Sailing in the Caribbean

Sailing in the Caribbean promises turquoise waters, steady winds, and an array of island destinations. This guide provides an in-depth look at Caribbean sailing for international sailors – from seasonal weather patterns to regional highlights, required skills, charter options, and local etiquette. Whether you’re a novice looking for gentle cruising grounds or an expert seeking bluewater challenges, the Caribbean has something for everyone.

Seasonal Weather and Wind Patterns

The Caribbean’s climate is famously tropical and generally warm year-round, but understanding seasonal wind patterns is key to planning a voyage. Trade winds prevail throughout the year, blowing steadily from the northeast to southeast.

The Caribbean Winter Season

In the winter dry season (approximately November through April), these trades average about 15–20 knots from the ENE–ESE, providing excellent sailing conditions with consistent wind​.

This period sees lower humidity, less rainfall, and generally calm seas – ideal for comfortable island-hopping. It’s also the peak season for charters, with popular anchorages bustling and many sailing regattas scheduled.

In winter months, sailors should be aware of the occasional “Christmas Winds.” These are stronger trade wind surges that typically occur in late December through January, when high-pressure systems produce several days of winds in the 20–30 knot range​. Christmas Winds can kick up choppier seas and require reefs in your sails, but they are usually short-lived, lasting a few days to a week. Additionally, winter can bring periodic north swell from Atlantic weather systems, which may affect north-facing bays (making some anchorages rolly or untenable). Wise sailors will check the swell forecast and seek south or west-facing harbours if large northerly swells are expected.

Sailing in the Caribbean’s Summer Season

The summer wet season (May through October) in the Caribbean is hotter, more humid, and features more frequent rain showers and squalls. Winds in summer tend to be lighter and can be more variable, often blowing 10–15 knots from the southeast, with calms or localised gusts around thunderstorms.

This season also coincides with the hurricane season, which officially runs from June 1 to November 30, with peak activity in August and September. During this period, the risk of tropical storms and hurricanes is higher (especially in September–October​), so sailors need to plan carefully. Many charter companies restrict operations or require hurricane waivers in these months.

Some southern parts of the Caribbean (e.g. Grenada or the Grenadines) lie on the fringe of the hurricane belt, but they are not entirely immune. If you do sail in the summer, keep itineraries flexible, monitor tropical weather forecasts closely, and have contingency plans for safe shelter or evacuation in case of a storm.

Caribbean Sailing Shoulder Seasons

Shoulder season months like May, early June, and November can be ideal times to sail. You’ll enjoy warm weather and fairly steady winds with fewer crowds, as well as reduced charter rates. Early summer (June–July) often still has consistent tradewinds and only occasional squalls before the heart of hurricane season hits​. Whenever you choose to sail, remember that tropical weather can be dynamic – always listen to local marine forecasts (VHF radio weather channels or online updates) for the latest conditions.

Best Sailing Season in the Caribbean

The best sailing conditions are typically in late fall through spring for stability and breeze. However, each season in the Caribbean has its charms: the winter brings the liveliest winds and sailing festivals, while the summer offers solitude and warm evenings (albeit with an eye on the weather radar). By timing your trip with the seasonal patterns, you can make the most of what the Caribbean winds have to offer.

Caribbean Sailing Regions

The Caribbean is not a single cruising ground but a tapestry of distinct regions, each with its own geography, weather nuances, sailing conditions, and shore facilities. Below, we cover the main regions – including the British Virgin Islands, the Bahamas, the Leeward and Windward Islands (eastern Caribbean chain), and the Grenadines – comparing their characteristics and the skill levels they demand.

British Virgin Islands (BVI)

Geography and Sailing Conditions

The British Virgin Islands are an archipelago of around 60 islands and cays clustered in a compact area at the northeastern edge of the Caribbean Sea​. The four largest islands (Tortola, Virgin Gorda, Jost Van Dyke, and Anegada) are surrounded by many smaller islets, creating a wonderful playground for sailors. Distances between anchorages are short – often just a few nautical miles – and most navigation is line-of-sight.

The islands (except low-lying Anegada) are hilly, which means many bays are well protected from open-ocean swell. The Sir Francis Drake Channel, running between Tortola and the smaller southern islands, acts like a sheltered highway with flat seas and consistent winds. Overall, the BVI offers easy sailing: steady tradewinds around 10–20 knots, gentle seas, and very few hidden hazards. Tides are minimal (under 1 foot) and currents are weak (perhaps 0.5–1 knot)​, so you won’t be fighting strong flows or complex navigation.

This forgiving environment makes the BVI ideal for beginners and relaxed cruising. In fact, it’s often called “the sailing capital of the Caribbean” because it caters so well to casual sailors. You can typically reach your next destination in 1–2 hours of sailing, which leaves plenty of time for snorkeling, beachcombing, and island exploring each day. The only moderately challenging area is the approach to Anegada, a flat coral island on the fringe of the group – it’s surrounded by reefs and shallows, so careful navigation (and good charts) are required if you venture there. Otherwise, hazards are few and well-marked. New sailors will appreciate that the BVI has far fewer reef challenges than places like the Bahamas.

Weather in the BVI

The BVIs enjoy the classic Caribbean tradewind climate. From December to April, expect very reliable NE-E winds (15–20 knots) and sunshine, with occasional stronger gusts during Christmas wind events. Summer brings lighter winds and some squalls, but year-round, the weather is generally friendly. Because the islands are close together, you’ll often be sailing in the lee (wind shadow) of an island or quickly finding lee after a short channel crossing, so conditions stay comfortable. Brief rain showers may roll through, but they tend to pass quickly. As with the rest of the region, hurricanes are a consideration in late summer – direct hits are infrequent but not unheard of (the BVIs were severely impacted by hurricanes in 2017, for example). During hurricane season, many yachts either leave the area or have storm plans in place.

Harbours in the BVI

The BVI boasts some of the best maritime infrastructure in the Caribbean for cruising yachts. There are numerous marinas and yacht clubs, especially on Tortola (e.g. Road Town and Nanny Cay) and Virgin Gorda (Spanish Town, Leverick Bay). These offer fuel docks, water refills, showers, and provisioning shops.

Popular anchorages like The Bight at Norman Island, Cane Garden Bay, North Sound, and Great Harbour (Jost Van Dyke) are equipped with dozens of mooring buoys for visitors. In fact, picking up a mooring ball each evening is more common here than anchoring, as it’s convenient and protects the seabed from anchor damage. Overnight mooring fees are typically around $30 (often payable to a local warden or via an app in some locations)​.

Anchoring is still allowed in many bays (look for sandy patches to drop the hook), but in marine parks or very popular spots you’ll be asked to use moorings. Navigation aids are present on major routes, and charts are excellent.

Onshore, the BVIs are extremely cruiser-friendly. You’ll find beach bars, restaurants, and even dedicated dinghy docks at many stops (for example, the famous Soggy Dollar Bar in Jost Van Dyke, or Foxy’s). Services like garbage disposal, laundry, and boat repairs are readily available around Tortola. Because the charter industry is big business here, support services are excellent – if you have a mechanical issue with a charter boat, the base can usually dispatch a chase boat or technician to assist quickly. The concentration of boats does mean that in peak season anchorages can fill up by mid-afternoon, so the protocol is to arrive early to snag a mooring. Also note that night sailing is generally not allowed for charterers in the BVI (and not advisable given the many reefs and yachts); plan to be moored for the night at least an hour before sunset.

Required Skill Level: Beginner to Intermediate.

The BVI is often recommended as a first bareboat charter destination because of its forgiving conditions and support. It’s perfect for sailors with basic skills – you should be comfortable handling a yacht in moderate winds and know how to anchor or moor, but you won’t need advanced navigation techniques.

Routes are simple and mostly in protected waters. Even relatively inexperienced crews can safely enjoy island-hopping here. That said, complete novices might still hire a skipper for the first day or two just to get familiar with the boat and area. More seasoned sailors also love the BVI for its laid-back sailing; while not challenging, it offers great recreation and line-of-sight passage-making. The BVI in many cases is considered a Level 1, so a nice place for beginners.

The Bahamas

Bahamas Geography and Sailing Conditions

North of the Caribbean Sea, the Bahamas is an expansive archipelago of hundreds of low-lying islands and cays stretching over 500 miles of the Atlantic. Two areas particularly popular with sailors are the Abacos (in the northern Bahamas) and the Exumas (central Bahamas). Bahamas sailing is a very different experience from the Eastern Caribbean islands.

Here the scenery features shallow turquoise banks, sandbars, and coral heads rather than tall volcanic isles. The sea bottom is often clearly visible – and often alarmingly close under your keel! Depths on the Bahama Banks can be just a few metres (or less), so navigation requires constant vigilance. Unlike the BVI, you won’t always have deep channels; instead, you “read” the water by its colour (bright green or pale blue indicates shallows, deep blue indicates deeper water).

Winds in the Bahamas still follow a tradewind pattern but with some twists. In winter, the winds are generally NE-E around 15 knots, similar to the Caribbean, but the Bahamas can also be affected by North American weather. Winter cold fronts occasionally sweep down, bringing westerly or northerly winds that can turn anchorages exposed to those directions into uncomfortable spots. These fronts can also kick up short-term gales or squalls even under otherwise sunny skies. In summer, winds often lighten and can be SE or variable, with afternoon thunderstorms. The Bahamas also have a hurricane risk in late summer/autumn (the northern Bahamas have seen a few very strong hurricanes in recent years).

Seas around the Bahamas are mostly small when you’re inside the shallow banks, because the reefs and banks break the ocean swell. However, to move between island groups you may need to sail through cuts or in the open Atlantic. For example, in the Abacos, boats must often transit “Whale Cay Passage” (going briefly into the ocean around an outlying cay) to reach the southern cays – this short voyage can be rough if ocean swell is running. Similarly, in the Exumas, sailing outside the reef on the sound (ocean) side can mean encountering larger swells and stronger winds than on the bank side. Planning routes with weather and tide in mind is essential.

Bahamas Navigation and Hazards

The Bahamas are known for offering more technical navigation challenges. Charts and GPS are critical, but so is old-school piloting using your eyes. Coral heads dot many areas (especially in the Exumas and farther south), and shifting sands mean some charted depths change over time. Tidal ranges are larger here than in the Eastern Caribbean – up to about 3 feet in some areas – and tidal currents through narrow cuts between cays can be swift. This means timing your passages through reef openings (for example, entering an anchorage from the ocean) at slack tide or with favourable currents becomes important. You’ll also need to account for tides when anchoring in very shallow areas, to ensure you don’t end up aground at low tide. While all of this is manageable, it’s certainly a step up in complexity compared to line-of-sight, low-tide BVI sailing.

Because of these factors, the Bahamas are considered an intermediate sailing ground. One cruising guide puts it plainly: “Sailing in the Exumas is not for beginners – you need to understand tides, conduct weather planning, and navigate by reading the colour of the water.”​ That said, within the Bahamas, the Abacos are somewhat more beginner-friendly than the Exumas. The Abaco Sea is a protected lagoon with mostly sand bottom and a few well-marked channels; it has resorts and marinas that cater to charterers. The Exumas chain, by contrast, is more remote: you’ll be anchoring out almost every night and dealing with more reefs.

Bahamas Harbour Infrastructure

The Bahamas has fewer full-service harbours than the Caribbean’s main islands. In the Abacos, Marsh Harbour and Treasure Cay were the primary yacht hubs (though they are rebuilding after hurricane damage). They offer marinas, fuel, water, and fairly large grocery stores. In the Exumas, Nassau (on New Providence Island) is often the start point – Nassau has big supermarkets, marine stores, and marinas for provisioning and preparation. Once you depart Nassau for the Exuma Cays, however, amenities become sparse. There are a couple of small marinas (e.g. at Highbourne Cay, Staniel Cay, and Emerald Bay near Great Exuma), but many nights you will be anchored off uninhabited islands or tiny villages. Mooring buoys are rare in the Bahamas; apart from a few in the Exuma Cays Land & Sea Park and perhaps at some private islands, you should be prepared to anchor every night. The good news is the holding is usually excellent in sand (bring a good scoop-type anchor), and the water is so clear you can often see your anchor on the bottom to ensure it’s well set.

Provisioning requires forethought

Stock up heavily on food, water, and supplies at your departure point (Nassau or Marsh Harbour), because once cruising, you’ll only find small stores with limited selections on the smaller cays. Prices for imported goods are high throughout the islands (plan for basics to be more expensive than back home). Many sailors plan a mid-trip stop at a settlement like Staniel Cay or Black Point which have small markets to grab extra bread, produce, or other essentials​. Fresh fish and lobster (in season) can often be caught or bought from local fishermen, which adds to the adventure. Regarding services, outside of major islands you won’t find much in the way of yacht chandleries or repair facilities – so ensure your boat is in good order before venturing far. In an emergency, you might have to sail a considerable distance back to Nassau or another large port for assistance.

Bahamas Required Skill Level: Intermediate

The Bahamas demand keen navigation skills and good skipper awareness. Charter companies typically recommend that at least one person on board have solid experience with coastal navigation and anchoring. Understanding tides and reading the water by sight are key skills here. While you don’t need to be an “expert” sailor in terms of heavy-weather sailing, you do need confidence in pilotage.

The Abacos could be handled by a confident intermediate sailor (especially outside of hurricane season), but the Exumas and farther south reward those with a bit more experience.

If you are a beginner, it’s wise to hire a local skipper or join a flotilla for a Bahamas cruise, or gain experience in easier waters first. For those with the know-how, the Bahamas offer incredibly rewarding cruising – isolated anchorages, dazzling water, and the challenge of mastering a unique sailing environment. Just be ready to handle your own anchoring every night and stay alert for shifting sandbanks and reefs at all times.

Leeward Islands (Northern Eastern Caribbean)

Leeward Islands Geography and Overview

The Leeward Islands form the northern half of the eastern Caribbean island chain (the Lesser Antilles), running roughly south from the Virgin Islands down to Dominica. Key sailing areas usually grouped as Leewards include Anguilla, St. Martin/Sint Maarten, St. Barths, Saba, St. Kitts & Nevis, Antigua & Barbuda, Montserrat, and Guadeloupe (and sometimes Dominica). This region offers a mix of larger islands (like mountainous Guadeloupe or Antigua with its many bays) and small islands (like the low-lying coral atoll of Barbuda, or the steep pinnacle of Saba). Unlike the compact BVI, distances here are greater and the sailing is more offshore in nature. You will often be sailing from one island country to another on half-day or full-day passages across open water.

Leeward Islands Wind and Sea Conditions

The tradewinds blow through the Leewards much as they do further north, generally from the northeast or east in winter and more east-southeast in summer. Wind strength is typically 15–20 knots, but can be higher in accelerated gust zones around certain headlands. Because the islands are spaced farther apart (often 20–50 nm between major stops), you will encounter more open-ocean swell and chop on passages. For example, sailing from St. Martin to Antigua involves an open ocean leg that can have Atlantic swells of 6–8 feet with wind waves on top when the trades are up.

There are also notorious acceleration zones where the wind funnels between islands or around volcanic peaks – sailors often find a calm shadow behind an island followed by a sudden increase to strong winds at the edges of the shadow. Being prepared to reef sails for those gusty areas (and then shake out reefs in lulls) is part of Leeward Islands sailing.

Leeward Islands Navigation

Navigation in the Leewards is generally straightforward open-water navigation with GPS and sighting island landmarks. Unlike the Bahamas, reef navigation is less of an issue except near certain islands (for instance, Antigua and Barbuda have surrounding reefs to mind, and St. Martin has a few shoals). Each island usually has well-charted approaches.

Whilst night sailing is possible for experienced crews (and sometimes necessary for longer legs), many cruisers still prefer to do passages in daylight to admire the views and avoid any stray hazards. A nice aspect of the Leewards is that most islands are visible from one another on clear days – for example you can see St. Kitts from Antigua on the horizon – so you often have a visual reference.

Still, unlike the BVI, you might sail for several hours not seeing your destination until it slowly rises from the sea in front of you. A pretty cool experience nonetheless.

Harbour Facilities

The availability of marinas and moorings varies by island. St. Martin (the French/Dutch island) is a major yachting hub, famous for its sheltered lagoons. It has multiple full-service marinas (Port de Plaisance, Simpson Bay Marina, Fort Louis Marina, etc.), huge chandleries, repair yards, and even mega-yacht facilities. It’s one of the best places in the Caribbean for repairs or re-provisioning, with large supermarkets (particularly on the French side) stocked with international goods.

St. Martin’s popularity means crowded anchorages in season; the island provides many mooring buoys in areas like Grand Case and the nature reserve, and anchoring is also possible in designated zones.

Antigua also has a strong sailing culture – it hosts the annual Antigua Sailing Week regatta. Antigua offers Nelson’s Dockyard and Falmouth Harbour on its south coast, which have marinas, docks, and some med-mooring along the quay (Nelson’s Dockyard, a historic harbour, often has yachts stern-to with anchors or bow moorings). Jolly Harbour on the west coast is another marina with slips and amenities.

Outside of these, most of Antigua’s numerous coves require anchoring (with generally good sand bottom). Neighbouring Barbuda has almost no facilities – it’s a wild, flat island with exquisite beaches, where you’ll be anchoring off the shore and bringing everything you need with you.

Smaller islands like Nevis, St. Barths, and Saba each have unique setups: Nevis and St. Kitts have some moorings off their main towns and a few small marinas for local boats; tiny St. Barths (St. Barthélemy) is upscale and has a harbour at Gustavia where visiting yachts med-moor along the quay or take a mooring outside – it’s common to stern-tie in Gustavia’s inner harbour (space is limited and reserved for smaller yachts, with larger ones anchored outside). Saba has no real beaches or natural harbours at all – it provides a handful of moorings on the west side for visiting boats (anchoring is extremely deep and not recommended), making it a destination only in settled weather.

Montserrat, with its active volcano, has an anchorage at Little Bay but no marina – yacht visits there are more for the adventurous souls.

Inter-island Customs

One important aspect of cruising the Leewards is dealing with multiple countries. Each island (or island pair) is often a separate nation or territory. For example, Anguilla is British, St. Martin is split French/Dutch, Antigua & Barbuda is an independent nation, etc. This means you will be clearing customs and immigration frequently as you sail from one to the next.

Fortunately, several of these islands use a common electronic clearance system (SeaClear/SailClear), and the process is usually straightforward, if a bit time-consuming. Always ensure you officially clear out of one country (obtaining clearance papers) before sailing to the next, where you must clear in. Skipping customs is taken seriously; expect fines if you fail to check in properly. (We’ll detail the general customs protocols in a later section, but keep this in mind when route planning in the Leewards – you may need to arrive at specific ports of entry.)

Required Skill Level: Intermediate to Advanced

The Leeward Islands present more challenging sailing than the protected waters of the BVI. They are best suited to sailors with some offshore sailing experience. You should be comfortable handling your vessel in open ocean conditions, including potentially brisk winds and sizable swells.

Docking stern-to in a harbour like Gustavia or English Harbour requires boat-handling skill. Additionally, managing longer day sails (50+ nm) and navigating around varying island geography calls for solid seamanship. Charter companies often rate destinations like Antigua or St. Martin as more advanced – for instance, Sunsail classifies Antigua as a Level 2 (intermediate) destination and St. Martin as Level 3 (advanced)​. This doesn’t mean you must be a veteran ocean sailor, but at least one crew member should have experience in similar conditions.

If you’re relatively new to sailing but eager to explore the Leewards, consider hiring a local skipper or joining a flotilla for added support. Those with a bit of coastal cruising under their belt will find the Leewards a fantastic step up – offering exhilarating sails between islands and a chance to hone navigation and weather-reading skills.

Windward Islands (Southern Eastern Caribbean)

Windward Islands Geography and Overview

The Windward Islands form the southern half of the Eastern Caribbean chain (the Lesser Antilles), traditionally comprising Dominica, Martinique, St. Lucia, St. Vincent, the Grenadines, and Grenada (Barbados, lying to the east, is also often included geographically, though it stands alone).

These islands are generally more lush and mountainous the further south you go, with active volcanoes on some (like in St. Vincent and Dominica). The sailing down here is again sometimes referred to as “blue water” cruising because you’re in more open sea conditions with the full force of the tradewinds. However, the chain is still linear, so you often have the option to sail on the lee side (western side) of the islands where waters are calmer, then make channel crossings in between.

Windward Islands Wind and Sea Conditions

The tradewinds in the Windwards tend to blow a bit more consistently from the east and can be strong, especially in the channels between islands. It’s common to have 20–25 knot winds in the winter through these gaps. Sailing southward (e.g., from St. Lucia down to Grenada) is usually a pleasant broad reach with the wind on your aft quarter, whereas going northward can mean hard on the wind if it’s easterly. Either way, expect lively passages.

The channels – such as between Dominica and Martinique, or St. Lucia and St. Vincent – are essentially open Atlantic stretches and can be choppy with 6–8 foot wind waves and occasional larger swells rolling in. It’s not unusual to get splashed with warm sea spray as your boat cuts through the trade-wind chop! By contrast, once you tuck behind an island, the wind often eases and seas flatten until you approach the next gap.

One noteworthy feature in the Windwards: the tall islands create significant wind shadows and katabatic winds. For instance, behind Martinique or St. Vincent, you might run into a dead calm a few miles offshore in their lee, or find that wind comes from an unexpected direction due to land breeze effects.

At night, cold air rushing down mountains can cause strong downdrafts in anchorages (sudden gusts in the middle of the night that test your anchor set). Sailors in places like the bay of Deshaies, Guadeloupe or the Pitons of St. Lucia often speak of midnight gusts that spin the boat around. These micro-scale wind quirks keep you on your toes, but they are part of the character of Windwards sailing.

Windward Islands Notable Areas and Routes

A popular itinerary is St. Lucia to Grenada one-way, which takes you through St. Vincent & the Grenadines. This route is well-liked because it’s mostly downwind. Another common starting point is Martinique, a French department with a large charter base at Le Marin.

Martinique’s modern marinas and European flair make it a convenient provisioning spot before heading to the more remote islands southward or exploring Dominica to the north.

Dominica, while officially part of the Windwards, stands out as a pristine natural gem with limited facilities – it’s more of an adventurous stop for those who love unspoiled rainforests (Dominica has mooring buoy installations in places like Portsmouth and Roseau now, partly to help visiting yachts since anchoring can be deep).

Windward Islands Harbours

The Windward Islands offer a mix of well-developed ports and very basic anchorages:

• Martinique: As an overseas region of France, Martinique has excellent yachting facilities. Le Marin in the south is one of the largest yacht harbours in the Caribbean, with hundreds of berths, repair yards, chandleries, and supermarkets full of French wine and cheese (a cruiser’s paradise for stocking up!). Fort-de-France (the capital) also has anchorage space and nearby dock facilities. You can find fuel, water, and even luxuries like marine electronics shops easily on Martinique. Many mooring buoys exist in smaller bays (often managed by local municipalities or parks).
• St. Lucia: The main yacht centers are Rodney Bay in the north (a large marina and enclosed lagoon) and Marigot Bay and Soufrière/Pitons area in the southwest. Rodney Bay Marina offers slips, fuel, water, shops, and restaurants – it’s a hub where events like the ARC (Atlantic Rally for Cruisers) finish. Marigot Bay has a small marina resort and moorings. Soufrière has a marine management area with park moorings (anchoring is restricted near the famous Pitons to protect coral). St. Lucia has fewer marinas than Martinique, but the basic needs are covered, and it’s very welcoming to cruisers.
• St. Vincent: The main anchorage is at the south end (Blue Lagoon/Young Island Cut) which has a marina and charter base. However, many charter itineraries don’t spend much time on the big island of St. Vincent itself, instead focusing on the Grenadines. Bequia, just south of St. Vincent, is the first of the Grenadines and a beloved sailor’s haunt – its Admiralty Bay is a wide anchorage with dozens of yachts swinging at anchor or on a few moorings. Port Elizabeth in Bequia has dinghy docks, beach bars, provisions, and some services (water and fuel via local barges or at the small dock). The Grenadines (we will cover them in detail next) continue southwards. At the end of the chain, Grenada is a major cruiser base again – with several marinas (Port Louis, Prickly Bay, etc.), a large haul-out facility, and a vibrant sailing community, especially during hurricane season when many cruisers head to Grenada for relative safety.

In general, as you sail further south in the Windwards, the infrastructure becomes sparser until you reach Grenada. So it’s wise to top off fuel, water, and groceries in places like Martinique or St. Lucia, because by the time you’re in the heart of the Grenadines, you’ll be relying on small island resources.

Required Skill Level: Intermediate to Advanced

The Windward Islands are often considered a Level 3 (expert) charter area by companies​. That doesn’t mean you need an ocean master’s certificate, but you should be a confident skipper in open water. You’ll be handling stronger winds on average, making longer passages, and visiting less sheltered anchorages at times.

Expect to use all your sailing skills: reefing sails appropriately, navigating without land in sight for a few hours, anchoring in deep waters or gusty conditions, and potentially executing a Med-moor or tricky harbour entry on occasion. For example, anchoring at the picturesque Tobago Cays (in the Grenadines) requires threading through a reef to enter, then anchoring in relatively shallow patches of sand amid strong currents – a task for a competent crew with good teamwork.

However, this region is by no means off-limits to recreational sailors – thousands of cruising sailors explore the Windwards every year. It’s about preparation: if you have moderate sailing experience (say, coastal cruising in varied conditions), you can step up to the Windwards, perhaps starting with a shorter itinerary (like Martinique to St. Lucia and back) to get a taste.

Many sailors build experience in the BVIs or Med and then charter in St. Lucia/Grenadines for a bit more adventure. If in doubt, take a skipper for the first day or two to guide you through the learning curve, or join a group of more experienced sailors.

When you do rise to the challenge, the Windwards reward you with some of the most dramatic scenery – from the towering Pitons of St. Lucia to the emerald rainforests of Dominica – and the satisfaction of having sailed “outside the kiddie pool,” so to speak.

The Grenadines

Note: The Grenadines are technically part of the Windward Islands (they lie between St. Vincent and Grenada), but they deserve a special focus. This chain of small islands is often considered a standalone cruising ground because of its unique charm.

The Grenadines Geography and Highlights

The Grenadines refer to the collection of islands that are split between two countries: the northern portion (including Bequia, Mustique, Canouan, Mayreau, Union Island, and the Tobago Cays) belongs to St. Vincent and the Grenadines, and the southern portion (notably Carriacou and Petit Martinique) belongs to Grenada. These islands are relatively small (most are just a few miles across or less) and are sparsely populated, except for Bequia and Union which have small towns. The area from Bequia down to Union Island is one of the most popular charter itineraries for those seeking an authentic Caribbean vibe away from big resorts.

Sailing in the Grenadines feels like a step back in time – you’ll be doing short island hops, often within sight of multiple islands at once. The scenery is postcard-perfect: turquoise lagoons, palm-fringed beaches, and coral reefs teeming with fish. Many sailors cite the Tobago Cays – an uninhabited cluster of cays protected by a horseshoe reef – as a highlight of the entire Caribbean. Here you anchor off shallow sand flats with turtles swimming around your boat, under the gaze of an infinite starry sky at night (there’s no light pollution out there).

The Grenadines Sailing Conditions

Conditions in the Grenadines are strongly influenced by the trades. Winds are generally 15–25 knots from the east or southeast. Because the islands are small, they don’t block the wind much – you’ll have a good sailing breeze even when tucked behind an island (though a high island like Bequia does give some lee in its immediate shadow).

The channels between islands (for instance, between Canouan and Mayreau, or Union Island and Carriacou) are open to the ocean on the windward side, so they can have significant swell, especially if the wind has an ounce of north in it and brings Atlantic swell around the corner of the reefs. However, the distances are short; you’re usually only in the channel for an hour or two before arriving in the lee of the next island.

One consideration is that the area is more remote – if something goes wrong, you are a fair distance from the larger islands that have resources. So, skippers need to be more self-sufficient. Weather-wise, the Grenadines are slightly south of the typical winter “Christmas wind” zone, but they still get strong trade winds.

They also are far enough south that, statistically, fewer hurricanes pass directly over them – though as Grenada’s experience with Hurricane Ivan in 2004 showed, they are not immune. Generally, during hurricane season, many yachts base in Grenada and can still enjoy the Grenadines in the quieter summer months, keeping a close watch on tropical forecasts.

The Grenadines Harbours and Facilities

The Grenadines have limited but sufficient facilities for cruising yachts:

• Bequia (Port Elizabeth, Admiralty Bay): This is the yachting centre of the Grenadines. Admiralty Bay is a large natural harbour where you’ll typically anchor. There are a number of mooring balls closer to the town shore as well. Bequia has dinghy docks, beachside cafes, a few grocery stores (you can replenish basic provisions, fresh bread, fruits, etc. here pretty well), and services like laundry, fuel (available via a fuel dock or from a barge), and water (often delivered by boat or at the dock). It’s a meeting point for cruisers – expect to trade stories at the Whaleboner bar or Devil’s Table restaurant. Local entrepreneurs known as “boat boys” will come by offering everything from fresh baguettes and ice to lobster or to help arrange island tours. They’re generally friendly; a polite decline suffices if you don’t need anything.
• Mustique: This private island is famous for its celebrity villas. Yachts are welcome but must take one of the fixed mooring buoys (anchoring is discouraged to protect the seabed). There is a nightly fee and usually a limit on how long you can stay (e.g., 3 nights). Mustique has a couple of eateries (don’t miss Basil’s Bar) but no resupply stores to speak of for visiting sailors. It’s a lovely stop if you want a bit of “glam” and to see an island managed by a conservation-minded private company.
• Canouan: Canouan has a gloss of luxury (with a big resort and golf course), and a small settlement. There is a marina development (Glossy Bay Marina) that opened in recent years, bringing a safe harbour and modern docks to Canouan – useful if you need an ultra-protected berth or some marina amenities mid-trip. Otherwise, most cruisers might anchor off Canouan’s bays or skip it for other spots.
• Mayreau: This tiny island’s main anchorage is Salt Whistle Bay, a gorgeous curved beach separated from the Atlantic by a thin palm-covered sand spit. Salt Whistle is very snug – only a limited number of boats can anchor inside the bay. It’s first-come, first-served, and can get crowded in peak season. Many yachts that can’t fit there anchor at Saline Bay on Mayreau’s south side instead. Ashore, Mayreau has a very small village on a hill (reachable by a steep walk) with a couple of bars and one or two mini-shops. It’s charming and rustic.
• Tobago Cays: These are uninhabited, part of a marine park. You must anchor in sand patches here (anchoring on coral is forbidden and damaging – park rangers will enforce good environmental practice). There are now some moorings installed in parts of the Cays, which visitors are encouraged to use if available to reduce anchor damage. No services, no structures – just natural beauty. Park rangers come by to collect a small fee for park maintenance. If you need anything, local vendors from nearby Union Island often boat over in the afternoon to offer fresh fish or a beach barbecue dinner.
• Union Island: Clifton Harbour in Union is the southern hub of the St. Vincent Grenadines. It’s a reef-encircled bay with a marked narrow entrance. Inside, it’s mostly moorings (anchoring space is limited due to sea grass and crowded moorings). Clifton has a bustling village with shops, an open-air market (great for fresh produce and local goods), and a couple of small guest harbours. It’s a bit tight and can be breezy (holding onto a mooring with winds funneling is an experience!). Just west of Clifton is Palm Island (a private resort island) and to the south is Petit St. Vincent (another private resort island with a couple moorings off it). Leaving Clifton and heading to Grenada’s waters, you clear out of customs here (or in Carriacou further on).
• Carriacou (Tyrell Bay): As part of Grenada, Carriacou is often the check-in point when coming south. Tyrell Bay is a large anchorage where many cruisers linger. There’s now a small marina and boatyard, and a decent selection of shore amenities (groceries, fuel, beach bars). Carriacou has that slow, easy-going feel – an island of boatbuilders and fishermen. It’s a nice re-entry to “civilization” after the smaller Grenadines. From here, you’re a day sail or less to Grenada, where you can fully reprovision and prepare for whatever is next.

Required Skill Level: Intermediate

Sailing the Grenadines is one of the highlights of the Caribbean, and it’s quite doable for intermediate sailors who plan well. It’s somewhat less about technical navigation (reefs are present, but many anchorages have moorings or clear sand areas) and more about seamanship and self-reliance.

You should be comfortable anchoring in sometimes crowded or windy conditions, as anchoring is the primary mooring style in this region. Also, inter-island channels like between Canouan and Mayreau can produce rough seas at times; having experience handling your boat in strong winds or squalls is important.

If you’ve only sailed in very protected waters before, you might find the Grenadines challenging. But if you’ve got a few coastal passages under your belt and know how to trim sails for 20+ knots, you’ll be in good shape. Many people do hire a skipper for the first part of a Grenadines trip if they’re unsure, or they buddy-boat with another vessel for peace of mind.

Once you adjust, the rhythm of short daily sails and quiet natural harbours is pure bliss. Overall, the Grenadines fall in the intermediate range – harder than the BVI, easier than, say, a trans-ocean crossing – and hugely rewarding.

Charter Options: Bareboat, Skippered, and Crewed

When planning a Caribbean sailing holiday, one of the first decisions is what type of charter suits your skills and preferences. The main options are bareboat, skippered, or crewed charters. Here’s what each entails and the kind of experience you can expect:

• Bareboat Charter: A bareboat charter means you rent the yacht (sailboat or catamaran) and skipper it yourself, with your friends or family as crew. Essentially, you’re “the captain.” This option offers the maximum freedom – you can create your own itinerary, sail at your own pace, and have privacy with just your group on board. Bareboating is ideal if you have sailing experience and the confidence to handle navigation, anchoring, and boat handling on your own. In the Caribbean, bareboat charters are extremely popular in easy-to-sail areas like the BVI and increasingly available in many other islands as well. Before taking the boat, the charter company will usually brief you on the vessel and the local sailing area (points of interest, known hazards, weather tips, etc.). What it’s like: Imagine waking up with the sun at anchor, deciding on a whim which island to visit next, hoisting the sails and going – all on your schedule. You’ll be responsible for everything on board, from sailing to cooking (unless you hire a cook separately) to keeping an eye on the anchor at night. Many find bareboating a thrilling and empowering way to explore, essentially your own floating home for the trip. It’s important that at least one or two people in your party have sufficient sailing skills. Charter companies usually require a sailing résumé or certifications (discussed in the next section) to ensure you’re up to the task.
• Skippered Charter: This is essentially a bareboat charter with a professional skipper (captain) hired to come with you. The yacht is still private to your group, but you have an expert on board who handles the pilotage and navigation. A skipper will take responsibility for sailing the boat (though you and your friends can certainly help and learn), route planning (often in consultation with you on what you’d like to see), and they’ll ensure safe anchoring/mooring each night. What it’s like: A skippered charter is a great option if you lack experience, or simply want a more relaxed time without the stress of managing the boat 24/7. The skipper can act as a local guide too – being familiar with hidden gem snorkel spots or the best beach barbecue in the area. You still do the cooking and general daily living on board (unless you also hire a cook/hostess), but the skipper takes the heavy burden of boat handling. By the end of the trip, many guests feel like the skipper became part of the family, sharing stories under the stars. You also have the flexibility to be as involved in the sailing as you wish: if you want to practice your skills, most skippers are happy to teach and let you take the helm under their supervision. Or if you prefer to sunbathe and leave the work to them, that’s fine too! One thing to note is that the skipper will need their own cabin or berth on the boat, so factor that into the boat size (for instance, if you charter a 40-foot catamaran with 4 cabins, one would be for the skipper, leaving 3 for your use).
• Crewed Charter: A crewed charter is the luxury end of the spectrum. You charter the yacht along with a full crew – typically a captain and a chef/host, and on larger yachts possibly additional deckhands or stewards. This is common for larger catamarans and motor yachts. The crew handles all aspects of operating the vessel and hospitality: navigation, sailing, cooking gourmet meals, mixing your sunset cocktails, tidying up the cabins, and often acting as tour guides at destinations. What it’s like: This is an all-inclusive, floating villa experience. You discuss your preferences with the crew (often before the trip, you’ll fill out a preference sheet for food, activities, etc.), and they tailor the experience to you. Fancy a secluded bay all to yourselves? The captain will find one. Want to try kiteboarding or scuba diving? Many crewed yachts carry extra toys and have instructors. Every meal is prepared for you, often highlighting local Caribbean flavors (grilled fresh fish, tropical fruits, etc.). You can truly relax and indulge, focusing 100% on leisure and exploration. Crewed charters tend to be more expensive (since you’re paying for professional crew and a high-end vessel), but for many, it’s the ultimate holiday treat or a way to celebrate a special occasion in style. In terms of involvement, you can still participate in sailing if you ask – some captains will happily let you take the helm for fun – but there is no requirement to do any work on a crewed yacht. It’s all taken care of by a friendly team dedicated to your comfort and safety.

In summary, your choice depends on your experience and the type of vacation you want. If you’re an avid sailor eager for the hands-on adventure, a bareboat gives you freedom (and responsibility). If you want freedom but need a bit of guidance or relief from full-time captaining, a skippered charter is a perfect middle ground. And if you’re looking for a worry-free, upscale retreat on the water, a crewed charter will meet those expectations. Remember that even on bareboats, you can often add services à la carte – such as hiring a cook, or provisioning in advance – to ease some tasks, so there’s flexibility to customize your experience.

Qualifications and Certifications for Chartering

One common question for those new to chartering is: “Do I need a license or certification to charter a yacht in the Caribbean?” The answer varies by location and charter company, but here are the general guidelines and recommendations:

• No “License” Required in Many Places: Unlike driving a car, there isn’t a universal mandatory license for recreational boaters in many Caribbean countries. For example, the British Virgin Islands do not require a formal sailing license by law for bareboat charters​. Instead, charter companies rely on your sailing CV (résumé) or certifications as proof of competence. Similarly, in places like St. Lucia, St. Vincent & Grenadines, and the Bahamas, there isn’t a government-issued “sailing license” that you must hold to skipper a bareboat. However – and this is important – charter companies themselves will insist on evidence that you know what you’re doing. They carry the responsibility for the vessel and insurance conditions, so they won’t hand over a yacht to you unless you demonstrate sufficient experience or qualifications.
• Sailing Résumé: If you don’t have a formal certification, you will fill out a sailing experience form for the charter company. This details the yachts you’ve sailed, the waters you’ve navigated, and any relevant skills (anchoring, navigation, etc.). The company’s team will assess if your background matches the difficulty of the area and boat you want to charter. For an easy destination like the BVI, a history of a few years of coastal sailing and perhaps previous charter crew experience might be enough. For more advanced areas (Grenada, for instance), they may want to see that you’ve handled similar challenges before.
• Certifications (Recommended/Required): Obtaining a reputable sailing certification greatly smooths the charter process and is strongly recommended if you plan to bareboat regularly. The most widely recognised certificates for charter are those from the Royal Yachting Association (RYA) and the American Sailing Association (ASA), as well as the international ICC. Here are some key ones:
  • RYA Day Skipper (Practical): An RYA Day Skipper certificate (or higher, such as Coastal Skipper or Yachtmaster) is accepted by virtually all charter companies worldwide as evidence of competence. It certifies that you can skipper a yacht in familiar waters by day. Many British and European sailors carry this qualification. Along with this, many places (especially European waters) require a VHF radio operator’s certificate, but in the Caribbean this is usually not asked for specifically (though good to have).
  • ICC (International Certificate of Competence): The ICC is like a “boating license” that’s valid in many countries. It’s often issued based on having an RYA certificate or passing an assessment. While not formally required in the Caribbean, having an ICC is a quick way to show charter companies you meet an international standard. Some charter firms might explicitly ask for it if you’re chartering in a territory that follows European norms (for instance, Martinique, being part of France, might appreciate an ICC or equivalent).
  • ASA 104 Bareboat Cruising (and ASA 101/103 prerequisites): For American sailors, the ASA sequence of courses leads up to ASA 104, Bareboat Cruising, which certifies you to charter boats (usually up to a certain length). An International Proficiency Certificate (IPC) can be obtained from ASA for use overseas, which serves a similar role as the ICC. Major companies acknowledge ASA certifications; for example, having ASA 104 with some experience is typically enough to satisfy charter requirements for a mid-size boat. Charter companies often list ASA 104 or US Sailing Bareboat certification as an acceptable credential for bareboat charter​.
  • Other certifications: Various countries have their own systems (e.g., Canada’s International Yacht Training, or local licenses). Generally, any nationally or internationally recognized skipper certification will be considered. Some examples: NauticEd’s SLC (Sailing License & Credentials), German “Sportbootführerschein See”, etc., all can demonstrate your training​. If you hold something like a U.S. Coast Guard captain’s license, that of course is also more than sufficient.
• Regional Specifics: While most Caribbean locales don’t legally mandate a license, there are a couple of exceptions and practical considerations:
  • Belize: Outside the main scope of this guide’s regions, but worth noting: Belize does require skippers to obtain a temporary local certificate. Charter companies there will help arrange a “temporary captain’s license” issued by Belize authorities before you can take the boat​.
  • Bahamas: The Bahamas doesn’t have a government license requirement for foreign charterers, but the major charter companies operating there (e.g., in Abacos) tend to have stricter policies. They often require that the skipper and/or co-skipper hold a sailing certificate or significant experience. It’s not uncommon for Bahamas charter contracts to stipulate an ASA or RYA certification, because the conditions (as discussed) demand prudent seamanship. In fact, Sunsail specifies that in the Bahamas there must be at least one certified skipper on board, and they list acceptable qualifications like ASA 104, ICC, etc. Additionally, they note that Bahamian port authorities may request to see proof of competence​.
  • French Islands (Martinique, Guadeloupe): As departments of France, technically the regulations might require a license for operators of pleasure craft above a certain size. In practice, if you charter out of Martinique, the base will want to see an ICC or equivalent (RYA/ASA). It’s more of the company’s requirement than the gendarmes checking you on the water, but it aligns with international norms. So if you plan to sail in French territories, having your paperwork in order is wise.
• Experience vs. Certification: Charter companies do recognise that a piece of paper isn’t everything. If you have extensive sailing experience but no formal cert, don’t be deterred – list your experience in detail. You might be asked to do a brief check-out sail with a company captain to demonstrate your skills before they let you loose (especially if there’s any doubt). Conversely, if you just got an ASA 104 certificate but haven’t sailed outside of class, consider gaining more experience or taking along a seasoned friend. A cert alone doesn’t make you ready for every situation, but combined with real practice it’s powerful.
• Crew Requirements: Most bareboat charters require at least two competent adults aboard – typically a skipper and a co-skipper (first mate). The co-skipper doesn’t need a license but should be able to assist in sailing and emergencies. Some companies may ask for the co-skipper’s experience as well.

So while you may not need a license by law in many Caribbean spots, it is highly recommended (and sometimes effectively required by charter providers) to have a recognised sailing certification or a strong documented history of sailing experience.

For an international sailor, obtaining the ICC via an RYA Day Skipper course, or an ASA Bareboat Cruising cert, will make chartering in the Caribbean (and elsewhere) smoother and give you confidence in your abilities.

Always check with your specific charter company for their requirements well before your trip; if you find you’re missing something (like a VHF radio license or night sailing experience), you might have time to complete an additional course or adjust your plan (such as opting for a skipper on the first voyage).

Etiquette and Best Practices for Visiting Sailors

The Caribbean may be a laid-back paradise, but it has its own set of unwritten rules and etiquette that sailors are expected to follow. Respecting the environment, local regulations, and other mariners ensures everyone enjoys these waters for generations to come. Below are key codes of conduct and tips:

Environmental Etiquette

• Anchor with Care: Coral reefs and seagrass beds are vital and fragile. Always anchor in sand, never on coral or living seabed. Clear water makes it easier – you can often see the sandy patches. If suitable mooring buoys are provided (especially in marine parks or sensitive areas), use them rather than dropping anchor​ coralreef.noaa.gov. Damaging coral by anchoring is not only harmful but sometimes illegal. In places like the BVI and the Grenadines, you’ll find park moorings (often color-coded) near reefs – typically you’ll pick these up for day stops when snorkeling or visiting certain sites, and pay a small fee to the park authority.
• Waste Management: “Pack it in, pack it out” holds true. Never throw garbage overboard. Dispose of trash onshore in proper bins when you reach port. Plastics and litter can be deadly to marine life (for instance, turtles mistake plastic bags for jellyfish). Many islands have limited waste disposal infrastructure, so reducing waste (say, by removing excess packaging before you set sail) is helpful. Also, no discharge of pollutants: use holding tanks for toilet waste when inside harbors or near shore – in some areas it’s legally required to only discharge black water beyond a certain distance offshore. Protect the clear water that you came to enjoy.
• Conserve Water and Energy: Fresh water can be scarce on small islands. If your yacht doesn’t make its own water, be mindful of consumption – take short “Navy” showers, don’t leave taps running, etc. Many charter yachts have solar panels or wind generators; still, be conscious of power usage to avoid running the diesel generator excessively, especially at night (noise travels across calm anchorages and can disturb others).
• Marine Life Respect: When snorkeling or diving, look but don’t touch. Disturbing coral, feeding fish, or chasing turtles is discouraged. Fishing is fun, but observe local regulations – some zones are fish sanctuaries where fishing is prohibited. Spearfishing is illegal in certain countries or restricted to locals with permits. If you’re keen on catching your dinner, ask about the rules in each area (and note conch and lobster often have closed seasons to prevent over-harvest).

Anchoring & Mooring Protocols

• Anchorage Etiquette: Popular anchorages can get crowded by late afternoon. When you arrive, take stock of the boats already anchored or moored. Give ample space when choosing your spot – not just for the current conditions, but also considering how your boat will swing if wind or tide changes. A good rule of thumb is to stay out of the radius of others’ anchor rodes. If someone was there first, it’s on you to anchor far enough away. If you must squeeze into a tighter spot, politely talk to nearby boats to coordinate and ensure everyone is comfortable with the spacing.
• Rafting Up: In the Caribbean, rafting (tying multiple boats together on one anchor or mooring) is generally only done by agreement (e.g., a group of charterers traveling together). Don’t raft onto a stranger’s boat without permission – it would put extra strain on their anchor. Many mooring buoys are one boat per buoy unless specified.
• Use of Mooring Balls: In areas with many moorings (BVI for instance), the etiquette is usually first-come, first-served. Some places have online reservation systems (like BoatyBall in the BVI for certain moorings). Otherwise, you cannot “reserve” a mooring by hovering or leaving a dinghy – you must physically occupy it with your yacht. If you arrive late and moorings are all taken, be prepared to anchor outside the mooring field. When picking up a mooring, approach slowly into the wind, have crew ready at the bow with a boat hook and mooring line, and secure both bow lines through the eye for security (charter briefings will usually cover the proper method).
• Respect Quiet Hours: Sound carries far over water. After sunset, most cruisers seek a peaceful atmosphere. It’s fine to have fun at the beach bar, but keep music and noise on your boat to reasonable levels when back aboard, especially later in the evening. Conversely, if you plan a party night with loud music, choose a spot isolated enough or perhaps go to a marina dock where such activity is more expected.
• Dinghy Conduct: The dinghy (tender) is your car on the water – and it too has etiquette to follow. Go slow (no wake) when driving through anchorages where people are swimming or boats are at rest. Use dinghy docks if available rather than tying to random piers or trees without asking. At a crowded dinghy dock, tie up short and make room for others; don’t lock the dock by roping your dinghy in a way that blocks access. And always lift and secure your dinghy at night or when leaving it – dinghy theft, though not rampant, can happen, so better safe than sorry (plus a drifting dinghy is a nuisance).

Customs and Immigration Protocols

• Check-In/Check-Out: As you cruise between islands, you will encounter different nations and customs requirements. It is crucial to follow each country’s clearance procedures. Typically, upon arriving at a new country, the boat should proceed directly to an official Port of Entry (with the yellow “Q” flag hoisted), and the captain goes ashore with the crew passports, ship’s papers, and clearance from the last port. In many Caribbean ports, clearance involves visiting Customs, Immigration, and sometimes the Port Authority or Quarantine office. Dress respectfully (a shirt and shorts, not just swimwear) and bring a pen – you’ll fill out forms, often in duplicate or triplicate. Some countries (like the Bahamas) also require cruising permits or fishing permits to be purchased on arrival.
• Stay Onboard Until Cleared: A common rule is that no crew (and certainly no disembarkation of trash or stores) should happen before the vessel is cleared in. For instance, in Grenada, “Inward clearance must be completed by the skipper before any other crew member lands”​. So don’t send the family to the beach while you handle customs – technically everyone should wait on the boat until clearance is done (practically, this is often relaxed if you need to stretch legs, but ask permission if unsure).
• Clearance Papers: When you clear out of a country, you’ll receive a document clearing you out. You must present this when clearing into the next country. Losing it can cause headaches, so keep all papers in a safe folder. Some places use an electronic system (e.g., SailClear online clearance is used by many Eastern Caribbean nations to pre-fill forms). It’s wise to use these when available to speed up the process – you can submit crew info online in advance, then just report to officials and sign the printed forms.
• Fees and Attitude: Budget for various small fees – customs/immigration overtime fees (if you arrive on a weekend or after hours), cruising taxes, environment fees, etc. For instance, many islands charge a per person arrival or departure tax. It’s a good idea to have some local cash for these. Always be courteous and patient with officials – a friendly “Good morning” and a smile go a long way. Remember, the islands might have a slower pace, and you as a visitor must adjust to their procedures. If an official tells you to come back at a later time or to go from one office to another, just roll with it pleasantly. Challenging or ignoring procedures can land you in legal trouble or at least sour your experience.
• Documentation: Keep your boat’s documentation (registration papers or charter contract listing you as operator) and passports handy at all times during clearance. In some places each individual crew member might have to appear or sign; in others only the captain deals with it. Follow the guidance at each port.
• Courtesy Flags: It’s maritime tradition (and polite) to fly the courtesy flag of the country you are visiting from your starboard spreader. So, have on board a set of courtesy flags for the nations on your route. For example, if you sail from Martinique (France) to St. Lucia, you’d take down the French courtesy flag and hoist the St. Lucian flag after clearing in. Charter yachts often have a locker of flags – ask the base. The yellow Q flag should be flown from departure of one country until you’ve finished clearing into the next, then replaced with the courtesy flag of that nation.

Respect for Local Communities

• Cultural Sensitivity: Each island has its own culture and customs. Embrace the differences – whether it’s understanding that service might be relaxed and unhurried (island time is real!), or that local holidays/festivities could affect business hours. Learn a few greetings: a smile and a “Good afternoon” or “Bonjour” (in French territories) when greeting locals is courteous. In some smaller islands, modest dress is expected when not on the beach (i.e., shirt and shorts in town rather than just bikinis or shirtless men).
• Supporting Locals: Cruising sailors rely on local services, so it’s good etiquette to support the local economy in return. Buying produce at the village market, hiring a local guide for a waterfall hike, eating at that family-run beach shack – these interactions make your trip richer and help sustain these communities. When locals offer help (like guiding you onto a mooring or carrying groceries), it’s kind to offer a small tip for their time if you accepted the help. If you’re not interested, a polite “No thank you, we’re all set” works.
• Safety and Courtesy: The Caribbean is generally safe for sailors, but petty theft can occur. It’s courteous and smart to lock your yacht when you go ashore and to lock or lift your dinghy at night – not only does this protect you, it also prevents any temptation and trouble in the community. Use common sense (don’t flash valuables, respect any areas that locals advise against visiting at night, etc.). By and large, islanders are friendly and welcoming, and treating everyone you meet with the same warmth will enhance your journey immensely.

In essence, sail with a spirit of respect: respect for nature, for the laws of each island, for fellow sailors, and for the local people who call these islands home. This will ensure you leave only footprints in the sand (and not anchors on coral!), make friends along the way, and forge a positive reputation for the cruising community.

Mooring and Anchoring Styles in the Caribbean

Throughout your Caribbean sailing adventure, you’ll need to secure your boat regularly – whether for a lunch stop, overnight rest, or docking in a marina. The common mooring styles you’ll encounter are anchoring, mooring buoys, and occasionally Med mooring (stern-to). It’s helpful to know what to expect in each region and how to handle each style:

• Anchoring: This is the primary method of securing your yacht in most of the Caribbean, especially in areas with fewer installed moorings. Anchoring involves dropping your anchor from the bow and letting out sufficient scope (length of anchor chain/line) so that the anchor digs in and holds in the seabed. In the Caribbean, the seabed composition can range from perfect sand (excellent holding) to seagrass or rock (more challenging). Always try to seek out sandy patches – not only for environmental reasons but because your anchor is most likely to set well in sand. A typical scope is 5:1 or more (in calm conditions) – meaning let out five feet of rode for every one foot of water depth – or even 7:1 at night or in windy spots. Many charter boats have all-chain rode; make sure to use the provided snubber line to take strain off the windlass once anchored. After you drop anchor and let out scope, reverse firmly to set the anchor – you’ll feel it catch and the boat will stop moving if it’s well-set. Then take transits (line up landmarks) or use your anchor alarm on a GPS to ensure you’re not dragging. In crowded anchorages, you may need to consider dropping a second anchor or using a fore-and-aft anchor setup to limit swing, but this is rarely needed if everyone just gives enough space. Regional notes: In the BVI, anchoring is sometimes secondary to picking up a mooring buoy (given how many are available). In the Bahamas, anchoring is the norm, but be aware of tidal range – you might anchor in 8 feet at high tide only to find 5 feet at low! Also, the holding in fine white sand is great, but in areas of heavy seagrass your anchor might sit on top and not dig through to the sand; you may need to find bare sand patches. In the Windwards/Grenadines, anchoring is common everywhere except designated no-anchoring marine park zones. Depths can change quickly near reefs or shore, so watch your depth sounder and the water colour keenly.
• Mooring Balls (Moorings): Mooring buoys are floating balls attached by a line to a heavy fixture on the seabed (usually a concrete block or drilled pin). They have a loop or metal eye on top to which you attach your boat via a line. Moorings are prevalent in high-traffic or environmentally sensitive areas: for example, the BVI has hundreds of white mooring balls installed by private companies or park authorities; the US Virgin Islands national park waters have moorings to protect coral; many marine reserves (like the Tobago Cays or Saba Marine Park) have moorings for visitors. To use a mooring, approach slowly into the wind/current, have a crew at the bow with a line (one end secured on a bow cleat, free end ready to thread through the mooring eye). The crew uses a boat hook to grab the small pickup line or the eye itself and thread the line through, securing both ends back on the bow cleat (so you’re effectively making a loop through the mooring). Do not just tie one end – use two points of contact for security. Once secured, double-check there’s adequate slack so the mooring isn’t yanking your boat if waves come. Mooring balls usually have color codes: for instance, in BVI, overnight moorings are white with a blue stripe, day-use only moorings (often near reefs for snorkeling) are yellow or another color and not for overnight. Always make sure the mooring is in good condition – if the rope is very chafed or the buoy looks damaged, it might be unsafe. In popular areas, moorings can save a lot of hassle – you don’t worry about dragging anchor or the space needed to swing. They do come with a fee (payable to whomever maintains it, often a park ranger or via an honesty box system). In some places like the Moorings field in the BVI, staff come by in the evening or morning to collect fees, or you pay ashore. Regional notes: BVI & USVI: Moorings everywhere; expect to use them at most stops (The Bight, Cane Garden, Great Harbour, etc.). Leewards: Moorings in select spots – e.g., the national park in St. John, the Cousteau reserve at Pigeon Island Guadeloupe, off Les Saintes, etc. Windwards: Moorings are found in a few places like Soufrière Marine Park (St. Lucia) and Tobago Cays (SVG) but many anchorages have no buoys. Bahamas: Outside of a few marine parks (Exuma Cays Land & Sea Park has some), moorings are uncommon – you’ll anchor or occasionally dock at a marina instead.
• Med Mooring (Stern-to Mooring): “Med mooring” refers to the style common in the Mediterranean, where boats park stern-to a quay or dock, usually using an anchor or bow line to hold the front end away from the dock. In the Caribbean, true Mediterranean mooring is not widespread in public harbors, but you will encounter it in some marinas or town quays. For instance, the classic Nelson’s Dockyard in Antigua often has yachts med-moored (they will either drop their own bow anchor and back into the dock, or pick up a bow mooring provided by the marina and reverse to the wall). Gustavia, St. Barths requires visiting yachts to Med-moor along the inner harbor wall when space is available. Marinas in French islands sometimes use a variant: they have fixed mooring lines (ground tackle laid out from the dock) – the marina staff will hand you a line for your bow as you back in, instead of you using your anchor. In a med-moor situation, the typical procedure is: drop anchor at a calculated distance off the dock (or snag the provided mooring line), pay out the chain as you reverse towards the dock, then secure stern lines to the dock on both port and starboard quarters. Adjust tension so the boat is held a few feet off the dock (not banging into it even if waves come) and the anchor/line holds the bow in place. This can be challenging if you haven’t done it before – it’s a good idea to have fenders ready and a crew member or two managing the stern lines quickly. Often, marina staff or friendly boaters will help catch your lines. Outside of marinas, stern-to anchoring with a line ashore is occasionally practiced in small Caribbean coves to limit swing. For example, in parts of Grenada or the BVIs, if you tuck into a tight corner near rocks, you might put an anchor down and take a stern line to a palm tree or rock on shore. Unless you’re familiar and conditions demand it, it’s usually not necessary in the Caribbean (anchorages are roomy enough). But it’s a handy technique if you ever need to keep the boat from swinging due to proximity of reefs or other boats. Regional notes: If you plan to dock in any of the historic harbors (St. Barths, English Harbour Antigua, etc.), be prepared for med-mooring – often the harbourmaster will assign you a spot and expect you to execute this maneuver. Marina slips (with finger piers) are more common in the USVI/BVI, Puerto Rico, etc., so you might not med-moor there. Panama and Cuba (though not main topics here) also have some med-moor docking in certain marinas.

Docking in Marinas

Besides med-moor, the other style is the familiar alongside docking or slips. Many Caribbean marinas, especially those built or influenced by American standards, have alongside berths or piers (e.g., Nanny Cay BVI, Yacht Haven Grande St. Thomas, etc.). When you plan to enter a marina, contact them on VHF (usually channel 16 or a published working channel) as you approach to get docking instructions. They’ll often assign a slip and might send a dinghy or staff to assist. Tipping marina dock hands a few dollars for help with lines is a common courtesy.

General Tip

Whatever method you use to secure your boat, always double-check everything before leaving the boat unattended or turning in for the night. If anchored, snorkel or use a dinghy to visually inspect the anchor if water clarity allows – see that it’s well dug in. If on a mooring, check the condition of the mooring lines for chafe. If med-moored, ensure your anchor hasn’t loosened with the reverse pull. The peace of mind from a well-set boat allows you to fully relax and enjoy paradise!

Harbours, Provisioning, and Local Support

Being prepared and knowing what facilities are available can make your Caribbean voyage much smoother. Here are some tips on harbours, provisioning, and support services across the islands:

Harbour Hopping and Route Planning

• Plan Around Safe Harbours: The Caribbean has an abundance of natural harbours and anchorages, but they vary in protection. Plan your day’s sail so you arrive at a secure anchorage well before dark. Afternoon winds can be brisk, but they often ease near sunset, so arriving by 3–4 PM gives you the best pick of spots and calm conditions for anchoring. If uncertain about an anchorage’s holding or space, have a backup option (many pilot books list “if X is full or untenable, try Y just 2 miles away” advice). For example, if you find the anchorage at White Bay (Jost Van Dyke) too crowded, Great Harbour around the corner might have space.
• Popular vs. Offbeat Harbours: Mix up famous spots with lesser-known ones. The big-name harbours (e.g., Gustavia in St. Barths, Georgetown in Exuma, Road Town in Tortola) offer services and buzz, but the real magic of Caribbean sailing often lies in quieter bays. Don’t be afraid to spend a night in a nearly empty cove – just ensure it’s safe in forecast conditions. Often the charter briefing or locals can recommend a hidden gem bay that guidebooks overlook.
• Weather Shelters: In the unlikely event of extremely bad weather (strong gale or approaching tropical disturbance outside of hurricane season), know where the nearest hurricane hole or all-weather harbour is. These are usually mangrove-lined inlets or very enclosed bays where you can seek refuge. Examples: Paraquita Bay in Tortola (BVI) is a noted hurricane hole (requires special permission to use in a storm), Tyrrel Bay in Carriacou is very sheltered, Simpson Bay Lagoon in St. Martin provides enclosed anchoring. While routine charters won’t require this, it’s good seamanship to have a plan for foul weather. At a minimum, if squalls are forecast overnight, set extra anchor scope and maybe a second anchor if in a questionable spot, so you can sleep soundly.

Provisioning Tips

• Initial Provisioning: Most charter bases offer provisioning services – you can preorder food and drinks and have them on board when you arrive. This is convenient, though doing it yourself can be cheaper and lets you choose exactly what you want. In places like Tortola, St. Martin, Martinique, Grenada, Nassau etc., you’ll find large supermarkets. These often carry a mix of local products and imported goods (in the French islands, expect excellent baguettes, cheeses, and wines at reasonable prices; in the BVIs and Grenada, lots of UK/US brands but at higher island prices, etc.). Try to do a big shop at the start at one of these “stock up” locations.
• Fresh Produce & Local Foods: Take advantage of local markets for fresh tropical fruits, veggies, and fish. Many islands have a morning market or certain market days. For instance, Bequia’s produce stands by the harbor or St. George’s Market in Grenada (especially on Saturdays) are great for finding just-picked mangoes, plantains, etc. In the Bahamas, mail boats bring supplies weekly – timing your stop right after a mail boat arrives means better selection in stores. Buying local not only supports island farmers and fishermen but also gives you fresher and often tastier ingredients. Keep in mind storage on a boat: produce that lasts unrefrigerated (cabbage, carrots, green bananas that will ripen gradually, etc.) is useful, whereas delicate berries might not survive long.
• Seafood: Many sailors dream of catching their dinner. Trolling a fishing line while sailing can indeed yield mahi-mahi, tuna, or barracuda (careful with reef fish that may carry ciguatera toxin – locals can advise which fish are safe). If you’re not lucky with fishing, you can often buy fish or lobster straight from fishermen. In the Grenadines and parts of the Bahamas, fishermen come by in small boats offering their catch – negotiate a fair price and enjoy a super fresh meal. Lobster (spiny lobster) is seasonal (closed season typically April 30th through mid-July in many areas) – obey those to help stocks replenish.
• Water and Ice: Hydration in the tropics is important. If your boat has a watermaker, great – just ensure you run it in clean open water, not in harbor. If not, you’ll need to refill water tanks during the trip. Many harbours have a water barge or marina where you can get water (often for a fee per gallon). Plan water stops in your itinerary if you’re on a longer voyage – e.g., fill up in Road Town before exploring the outer BVIs, or top off in Union Island if heading toward the less inhabited southern Grenadines. Ice is a luxury turned necessity for many (who doesn’t like a cold rum punch at sunset?). Most populated cays have ice for sale (even if just at a beach bar or fuel dock). Stock up when you can; a cooler on deck with extra ice can help extend your fridge’s capacity during a hot week.

Local Support and Services

• Charter Base Support: If you’re on a charter, remember that your charter company is your biggest support asset. They usually provide a 24/7 emergency phone or radio contact. If you have a breakdown or problem, don’t hesitate to call them. In the BVI or other high-density areas, they might send a chase boat with a technician if needed. In more far-flung spots, they’ll coordinate with local contractors to assist. It’s in everyone’s interest to keep the boat safe and you happy, so use their support rather than silently struggling with an issue.
• Maintenance and Repairs: For those on longer journeys or their own boats, the Caribbean offers several hubs for repairs. St. Martin (Sint Maarten) is famed for its chandleries and technical services – you can find everything from riggers to electronics experts there. Guadeloupe (Pointe-à-Pitre) has good yacht repair facilities as well. Trinidad (Chaguaramas) and Grenada are known for haul-out yards and skilled labor, especially in hurricane season when many cruisers haul their boats there for storage or refit. Keep these hubs in mind if you need anything major. For minor repairs, ask around locally – island communities often have a “go-to” diesel mechanic or sailmaker, even if unadvertised. Other sailors on the VHF net or at the bar may point you in the right direction.
• Communications: VHF radio is the standard short-range communication tool. Monitor Channel 16 while at sea – you’ll hear important broadcasts like weather alerts or a nearby boat issuing a distress call (which hopefully you’ll never hear, but if you do, you might be in position to help). In popular cruising anchorages, there are often daily VHF “cruisers’ nets” on a set channel each morning, run by volunteers. These nets provide local announcements, weather, social events, and buy/sell offers among cruisers. They’re a great way to plug into the community. (For example, Grenada and St. Martin have very active cruisers’ nets, as do parts of the Bahamas.)
• Fuel and Spare Parts: Diesel and gasoline are generally available at most islands that have marinas or fishing fleets. Plan your refuel stops according to range. Some smaller cays have fuel only in jerrycans via local supply, which can be pricier – better to fuel up at main ports. Carry some basic spares in your kit: extra impeller, engine oil, fuel filters, light bulbs, spare lines, etc., if it’s your own boat. If it’s a charter, they’ll have spares for critical things stowed (and they’ll handle replenishing them if used).
• Medical and Emergencies: Health services in the Caribbean vary. Big islands like Guadeloupe, Martinique, Barbados, etc., have good hospitals. Smaller islands may have clinics for minor issues. For serious injuries or illnesses, sometimes evacuation to a larger island or even Miami may be considered. It’s wise to carry a good first aid kit on board and know basic first aid. In a true emergency at sea, use the VHF or sat phone to contact coast guard or regional maritime rescue (French islands have MRCC Fort-de-France, US areas use US Coast Guard in San Juan, etc.). While this rarely is needed, knowing how to say your position and nature of emergency over VHF 16 is basic seamanship.
• Friendly Locals: Don’t underestimate the value of local knowledge. Islanders can be incredibly helpful to sailors. From the dockmaster who might find you an extra adaptor, to the local sailor showing you the safest channel through a tricky reef, people are often happy to assist if you engage with respect. If unsure about something (can I dock here? Is it okay to swim there? Where can I find cooking gas?), just ask. Caribbean folks are generally proud of their home and eager to help newcomers appreciate it – and fellow cruisers are usually an equally valuable resource.

Finally, embrace the adventure aspect of provisioning and local interactions. Not everything will be like home – you might not find your favourite brand of cereal on a tiny cay, but you might discover delicious local johnny cakes for breakfast instead. You might have to dinghy a mile for water jugs in a pinch, or shower in a cool waterfall rather than under the boat’s limited water supply – but these moments often become cherished memories. With a bit of preparation, flexibility, and the supportive network around you, cruising the Caribbean will be the experience of a lifetime.

FAQs

Q: When is the best time to sail in the Caribbean?
A: The best time for Caribbean sailing is during the dry season, from late November through April. This period offers steady tradewinds around 15–20 knots, lots of sunshine, and minimal rain – perfect for comfortable passages. It’s also outside the hurricane season. December through March is the peak with the liveliest sailing and many fellow cruisers around. If you prefer fewer crowds and slightly lower prices, the shoulder months of May and November can be great – just on the edge of the rainy season but still generally good weather. Hurricane season runs June to November (peaking in Aug–Sep); while some experienced sailors do cruise then (especially in the far southern islands), it requires vigilance and flexibility (and often special insurance or charter agreements). In summary, for most people, winter and early spring offer the ideal mix of reliable weather and sailing events (regattas, festivals), whereas summer is off-season due to storm risks and hotter, more humid climate.

Q: Do I need a sailing license or certification to charter a boat in the Caribbean?
A: In most Caribbean countries, you are not legally required to have a license to skipper a recreational yacht (unlike in some European waters). However, charter companies will demand proof that you’re a competent skipper. This can be a sailing résumé detailing your experience and/or a sailing certification. It’s highly recommended to have a credential such as an RYA Day Skipper, ICC, ASA Bareboat Cruising (ASA 104), or equivalent, as these are widely accepted by charter firms as evidence of ability. Some companies, especially for certain destinations or larger yachts, make a formal qualification effectively required. For example, charters in the Bahamas often expect the skipper to hold a certification because of the navigational challenges. French islands (Martinique, etc.) might ask for an ICC or similar, aligned with European norms. So while you might not be asked to show a “license” to authorities, you should either have a recognized cert or solid skippering experience (with references) to satisfy the charter provider’s insurance and safety policies. If you lack these, you can still enjoy sailing by hiring a professional skipper to accompany you.

Q: Which Caribbean islands are best for beginner sailors?
A: The British Virgin Islands (BVI) are hands-down the top choice for beginners. The BVIs offer short hops between islands, line-of-sight navigation, and well-protected waters with plenty of safe anchorages and mooring balls. You can sail there with limited experience and build confidence. Another relatively forgiving area is the Abacos in the Bahamas – the sea there is mostly in sheltered shallows behind reefs (though you do need to be careful with navigation). St. Martin to Anguilla/St. Barths can be moderate if you stick to shorter sails on calm days. In contrast, areas like the Grenadines, St. Lucia, or St. Martin to Antigua involve longer open-water passages and stronger winds, better suited to those with some miles under their belt. If you’re a beginner wanting to sail outside the BVIs, consider joining a flotilla (group of boats led by a lead crew) or taking a skipper along for the first few days. But overall, if it’s your first bareboat charter or you have a novice crew, the Virgin Islands (both British and US) provide the easiest, most reassuring environment.

Q: What’s the difference between a bareboat, skippered, and crewed charter?
A: It boils down to crew and service:

• A bareboat charter means you rent the boat only – you are the captain (and chef, and crew, etc.). It’s DIY sailing: total freedom but all responsibilities on you. Ideal if you’re experienced and want independence.
• A skippered charter is a boat hire with a professional captain onboard. The skipper will handle navigation, piloting, and safety of the yacht. You and your friends can relax more, help as much or as little with sailing as you like, and benefit from the skipper’s local knowledge. This is great if you lack experience or want a stress-free time without worrying about the technicalities of sailing and mooring in unfamiliar waters.
• A crewed charter includes an entire crew – typically a captain and a chef/host as a minimum, sometimes additional crew for larger yachts. This is a fully serviced experience: they sail the boat, cook meals, mix drinks, tidy up, and often act as guides for activities. It’s akin to staying in a floating luxury villa with staff. You won’t need to lift a finger unless you want to. Crewed charters are usually on higher-end vessels (big catamarans, luxury monohulls or motor yachts) and the cost includes provisioning, gourmet dining, and personalized itineraries. In summary, choose bareboat if you want to sail yourself, skippered if you want guidance or lack qualifications, and crewed if you desire an all-inclusive pampered sailing holiday.

Q: How do customs and immigration work when sailing between Caribbean islands?
A: Whenever you sail from one country to another, you are required to clear out of the first country and clear into the next. Practically, this means: before leaving Country A, visit its customs/immigration office (at an official port) to get clearance documents. Then sail to an official port of entry in Country B and present those clearance papers, along with your crew’s passports and the ship’s registration, to the authorities there. Each country has its own fees and forms – for instance, clearance into the BVI involves some environmental and cruising permit fees; entering The Bahamas you’ll fill out arrival cards and buy a cruising permit (which covers fishing permit). The process is usually straightforward, and often the officials will guide you through it. Many Eastern Caribbean nations use an online system called SeaClear/SailClear that lets you pre-enter your crew and voyage info, speeding up the office visit. It’s wise to carry multiple copies of your crew list and boat docs. Always fly the yellow “Q” flag upon arrival until you’ve completed clearance, then switch to the courtesy flag of the country. Don’t forget to clear out when departing a country’s waters (failing to do so can cause issues when you try to clear in elsewhere). It might sound bureaucratic, but it becomes routine after the first couple of times. Budget a bit of time for it on travel days and remember it’s part of the experience – you often meet interesting fellow sailors at customs offices! If chartering, the base will brief you on local customs procedures and sometimes assist with paperwork.

Q: Is it safe to sail in the Caribbean and are there piracy or security concerns?
A: The Caribbean is generally a safe region for cruising sailors. Unlike some other parts of the world, piracy is not a common issue in the Caribbean islands that cruisers frequent. The only areas that have had piracy reports are well away from the charter circuits (for example, off the coast of Venezuela or some parts of Central America, which typical itineraries do not include). The island chains covered in this guide (BVIs, Leewards, Windwards, Bahamas) have no modern history of pirate attacks on yachts. You are far more likely to encounter friendly locals than any threat.

That said, petty crime can occur, as in any place where tourism mingles with economic challenges. The most common incidents are dinghy theft or occasional break-ins to unattended boats. To mitigate this: always lock your dinghy (with a cable to the dock or a lock on the outboard) when leaving it, especially in bigger towns. Lock your boat’s companionway or close it when you go ashore. Don’t leave valuable items in plain view in the cockpit. These simple steps greatly reduce temptation. Choose well-populated anchorages or marinas if you’re worried, and ask locally if any areas are best avoided.

Personal safety on shore is generally very good in tourist areas and villages alike. Normal precautions apply: stay aware of your surroundings, and if somewhere feels sketchy (few do in the island communities), then visit in daylight or with a group. Many islands have a community-based security or watch system in anchorages. For example, in Grenada, there’s an organized night watch that patrols popular bays and you can call them on VHF if needed.

Weather-wise, safety is about prudence: always check forecasts, especially for any potential storms or rough conditions. The biggest safety risk for sailors is weather and the sea itself (e.g., squalls, groundswells, coral reefs) rather than crime. Good seamanship – like keeping an eye out for coral heads, navigating with up-to-date charts, and not pushing on in unsafe weather – will keep you out of trouble.

In summary, the Caribbean is a welcoming and safe environment for sailors. By following basic security habits and seamanlike caution, you can expect a trouble-free cruise. Most sailors recount that the only “attacks” they suffered were from overly generous rum punch pours or perhaps a thieving seagull stealing their lunch!

Q: What kind of etiquette should I follow as a visiting sailor?
A: Caribbean sailing etiquette mostly boils down to respect – for nature, for other boaters, and for local customs. Some key points:

• Protect the reefs: Don’t anchor on coral or grass beds; use moorings or anchor in sand. Never toss trash overboard and be mindful of sewage discharge (use pump-out or open waters). Basically, leave no trace in the pristine environments.
• Anchoring courtesy: Give other boats ample space. The rule is whoever anchors or moors first has seniority; later arrivals must adapt. Avoid loud noise at night in quiet anchorages – sound travels far.
• Mooring manners: If you pick up a mooring, use proper technique (thread lines correctly) and pay the fee honestly. Don’t poach reserved or private moorings if they’re marked as such.
• Dinghy decorum: Go slow in dinghy zones, don’t create wakes near others. At docks, tie up efficiently and don’t block everyone else.
• Local culture: Greet locals politely, learn a few basic phrases, and be conscious of local norms (for example, some towns may appreciate modest dress away from the beach). Patronize local businesses in a fair way – haggling lightly at markets is okay, but remember a few dollars means more to a craftsperson than to a tourist, so be generous in spirit.
• Customs and laws: Adhere to each island’s rules – check in and out properly, respect marine protected areas (no fishing or only catch-and-release where mandated), and observe any park regulations (like no drone zones or permit requirements).
• Helping others: The sailing community is friendly – it’s good etiquette to lend a hand if you see a neighbor in a tricky anchoring situation or needing a jump-start for their engine. Pay it forward and it will come back to you.

By following these guidelines, you’ll get along wonderfully with both the cruising community and island residents. Essentially, be the kind of visitor that locals are happy to welcome back.

Q: Will I have access to marinas, fuel, and repairs if needed?
A: Yes, throughout the Caribbean there’s a network of marinas and support services, though density varies by region. In the BVIs, there are many marinas (Tortola alone has several) where you can dock, refuel, take on water, and get minor repairs done. In the Leeward and Windward Islands, each major island usually has at least one marina or yacht club facility – for example, Antigua has Falmouth Harbour Marina and others; St. Lucia has Rodney Bay Marina; Grenada has Port Louis and Prickly Bay marinas, etc. These places offer fuel docks, water, ice, and often amenities like showers, laundry, and Wi-Fi. Between those, smaller harbours might have just a fuel station or a town dock.

Fuel (diesel and petrol) is generally available somewhere on every inhabited island or island group that sees yacht traffic. We recommend refueling when your tanks are around half, just so you always have plenty in reserve. Keep in mind that in very remote cays, you won’t find fuel until you get back to a main island.

If your boat needs repairs, the best hubs for marine services are places like St. Martin (Sint Maarten), Antigua, Martinique, Grenada, and Trinidad. These have skilled labor and parts. Many charter companies have bases spaced through the islands (e.g., Moorings/Sunsail have bases in St. Martin, St. Lucia, Grenada, etc.), so they can coordinate support if you’re on one of their boats. If it’s your own boat, networks like local VHF nets and the Coconut Telegraph (SSB net) can connect you with mechanics and specialists.

In the Bahamas, outside of Nassau and perhaps Marsh Harbour (which have marinas and repair yards), services are thinner. The Bahamas are more remote, so you should be more self-sufficient if venturing far – bring spare parts and be prepared to jury-rig if needed until you reach a port. But for normal chartering in places like the Abacos or Exumas, the charter base support will handle any major issues by either guiding you or swapping boats if absolutely necessary.

Overall, you are never too far from help in the main Eastern Caribbean chain. It might be a day’s sail to a bigger island with a marina, but it’s accessible. Modern communication (mobile phones often work in range of populated islands, local SIM cards or Wi-Fi at cafes can get you internet) means you can usually call ahead to arrange what you need.

Q: Can I drink the water onboard and what about provisioning enough food?
A: Most charter yachts have water tanks filled with municipal or desalinated water – it’s generally safe to drink, though many people prefer the taste of bottled water or use a filter. If in doubt, ask the base if the tank water is potable. In some places (like the Bahamas), water is precious and some marinas produce it via reverse osmosis – it’s clean but can taste a bit flat. Many crews use tank water for cooking and washing, and keep bottled water for drinking. Be environmentally conscious and refill jugs or bottles from larger containers to minimize plastic waste.

Provisioning enough food is usually easy. All charter bases either provide a provisioning service or are located near grocery stores. Caribbean stores are quite well-stocked these days (you might be surprised to find familiar brands even on small islands, albeit at higher prices). The key is planning meals and snacks for the duration you’ll be away from shops. In the BVIs or USVIs, you’re never far from a store if you need something. In the Grenadines or remote Exumas, you might have several days without re-supply, so plan accordingly. It’s a good idea to plan a mix of meals: some nights you might dine ashore (be sure to experience local BBQ or seafood restaurants), other nights cook on board (grilling on the boat’s BBQ is a joy under the stars). Bring or buy any special dietary items in advance (for example, if someone needs almond milk or gluten-free products, get those in the larger supermarkets at the start).

One tip: provision a few extra days of food beyond your planned trip length, in case of any itinerary changes or just if you get extra hungry with all the swimming! Staples like pasta, rice, canned goods, etc., are good to have as backup. Also, don’t underestimate how much drinking water, soda, or beer you might go through in the tropical heat – better to have a little extra than to run low.

Q: What if I’ve never sailed before – can I still go on a Caribbean sailing holiday?
A: Absolutely! If you don’t know how to sail but want to enjoy the experience, you have a couple of options. You can do a skippered charter or join a crewed charter, where an experienced captain (and crew, if applicable) will handle the sailing for you. You get to do all the fun parts – snorkeling, island exploring, sunset cocktails on deck – without needing any sailing knowledge. It’s a fantastic way for non-sailors to experience the magic of cruising. Many people bring a skipper not because they can’t sail, but because it makes for a more relaxing vacation for everyone. You can be as hands-on or hands-off as you like; some guests end up learning a lot from the skipper during the trip (think of it like an informal sailing course in paradise), while others just sit back and relax.

Another way is to join a cabin charter or flotilla. Cabin charters (common on larger crewed catamarans) allow you to book a cabin and share the yacht with other guests – the voyage is managed by a professional crew. Flotillas are when you helm your own boat but follow a lead boat; however, since that still requires sailing skills for your own boat, a flotilla wouldn’t be for a true novice unless you had a hired skipper on your boat.

Finally, if your heart is set on learning to sail in the Caribbean, you could do a sailing course at a local sailing school (places like Antigua, Grenada, BVI have sailing schools offering RYA or ASA courses in warm waters). It’s a holiday and learning experience in one.

In short, you don’t need any sailing experience to enjoy a sailing vacation – just choose a format where professionals handle the hard stuff. You’ll quickly see why sailors love this life, and who knows, it might inspire you to take some lessons and come back as a budding skipper next time!

References

• David H. Lyman, “Understanding Wind in the West Indies,” Cruising World – Detailed insights into Caribbean tradewinds, seasonal variations, and local wind effects.
• The Moorings, “When is the Best Time to Sail the Caribbean” (2024) – Overview of Caribbean sailing seasons, weather patterns, and timing tips for charters.
• Kraken Travel, “Sailing in the British Virgin Islands” – Cruising guide highlighting BVI conditions (line-of-sight navigation, protected anchorages) and best season to visit.
• Matt Weidert, Yacht Warriors, “Sailing the Virgin Islands: What We’ve Learned” (2023) – Comparative look at BVI, USVI, Spanish VI, including cruising conditions and navigation notes (e.g., few hazards in VI vs Bahamas).
• Matt Weidert, Yacht Warriors, “Exumas Cruising Guide: Our Favorite Bahamas Sailing Destination” (2023) – Covers Exumas (Bahamas) challenges like tides, visual navigation, anchoring, and skill level required.
• Sunsail, “Sailing Destination Difficulty Rating Explained” – Charter company’s guide to experience levels needed for various locations (e.g., BVI as Level 1, St. Martin/Grenada as Level 3), and license requirements by destination.
• The Moorings BVI Charter Information – Charter company notes confirming no formal license required in BVI but sailing résumé needed, plus details on mooring fees and local regulations in BVI.
• NOAA Coral Reef Conservation Program, “Coral Etiquette 101” (2015) – Guidelines for boaters and snorkelers on protecting coral reefs (anchor in sand, use moorings, don’t touch marine life).
• Sunsail Grenada Base Guide – Includes customs clearance procedures in Grenada and the requirement of sailing experience Level 3 for that region, reflecting the advanced nature of Windward Island charters.