Sailing the Leeward Islands

The Leeward Islands offer some of the Caribbean’s most idyllic sailing grounds. From tranquil turquoise bays to vibrant port towns, this region caters to sailors of all experience levels. This guide provides an in-depth look at what to expect when sailing in the Leeward islands, including seasonal conditions, regional highlights, chartering tips, and practical advice for a smooth voyage.

Sailing Conditions in the Leeward Islands

Located in the northeastern Caribbean, the Leeward Islands enjoy a warm, tropical climate year-round. Steady trade winds blow predominantly from the northeast, providing reliable sailing breezes most of the year. There is little variation in temperature between seasons – expect daytime highs around 27–30°C (80–86°F) and balmy nights. However, rainfall and wind strength do change with the seasons:

Dry Season (Winter/Spring)

Roughly December through April, the climate is drier and the trade winds are steady (often 15–20 knots). This period offers prime sailing conditions with plenty of sunshine and generally moderate seas. Do note the occasional stronger “Christmas winds” in December–January, when gusts can reach 25–30 knots for short spells. Overall, winter and spring are the most popular and predictable months for sailing.

Wet Season (Summer/Autumn)

From June through November, the weather becomes hotter and more humid, with more frequent rain showers. Winds tend to ease to 10–15 knots in early summer and can become more variable. Hurricane season runs from mid-summer into autumn – tropical storms are possible any time from July, peaking in August and September. Many sailors avoid late summer voyages due to the hurricane risk, or they keep flexible itineraries and monitor forecasts closely. By late October and into November, conditions start to improve as storms subside.

Leeward Islands Sailing Conditions

Despite seasonal shifts, the Leewards are sailable year-round for those prepared to adjust to conditions. Always plan around weather updates during hurricane months. If sailing in off-season, consider shorter routes and have contingency plans for storms.

Key Regions and Required Experience Levels

The Leeward Islands stretch in an arc from the Virgin Islands in the northwest down to Dominica in the southeast. Within this chain, sailing conditions and required experience can vary by region. Understanding these differences will help you choose an itinerary suited to your skill level:

The Virgin Islands (USVI & BVI): Easy Island Hopping

The U.S. and British Virgin Islands lie at the northern end of the Leewards and are famously beginner-friendly. Distances between islands are short, often just a few nautical miles, allowing for line-of-sight navigation in protected waters. Numerous sheltered coves and bays mean you’re rarely far from a calm anchorage. The BVIs in particular have a well-developed sailing infrastructure with plentiful mooring balls, marinas, and repair services. These factors make the Virgin Islands ideal for less experienced crews or those seeking a relaxed cruising holiday. Even novice bareboat charterers feel comfortable here, thanks to the forgiving conditions and easy routes. The trade-off is popularity: expect busy mooring fields and many fellow charter boats in high season. Still, for stunning beaches, fun beach bars, and gentle sailing, the Virgin Islands are hard to beat for newcomers and families.

St. Martin, St. Barths & Anguilla

Cosmopolitan Sailing – Further south, the northern Leewards around St. Martin (Sint Maarten) offer a mix of upscale harbours and open-water passages. St. Martin itself is split into French and Dutch sides, giving a blend of European and Caribbean culture in one island. Nearby, stylish St. Barths (Saint Barthélemy) and low-key Anguilla are within a day’s sail. Sailing here is moderate in difficulty: while distances are still fairly short (20–30 nm between main islands), you’ll encounter more open ocean conditions than in the Virgins.

The channels (e.g. between St. Martin and St. Barths, or to Anguilla) can kick up with Atlantic swells and stronger winds, requiring good seamanship. Harbours like Gustavia (St. Barths) are well-organised but may require med-mooring or picking up bow-stern moorings due to crowding. Overall, this area suits intermediate sailors – those with some coastal experience who are comfortable with navigation and heavier winds on occasion. The reward is a diverse sailing experience: one day you’re snorkeling off an uninhabited islet, the next you’re dining in a chic French café. It’s a fantastic region for sailors wanting a bit more adventure while still enjoying accessible ports.

Antigua, Barbuda, St. Kitts & Nevis: Classic Cruising Grounds

The central Leeward Islands include Antigua and Barbuda, along with the smaller nations of St. Kitts & Nevis (and the British territory of Montserrat). Antigua is a historic sailing hub, known for its 365 beaches and annual regattas. It offers a mix of easy coastal cruising around Antigua’s leeward side and more challenging trips like the 30+ nm sail to Barbuda, which is a flat coral island with spectacular reefs. Navigation around Barbuda requires care due to coral shallows, so some experience is recommended. St. Kitts & Nevis, just to the west, are relatively close together (only 2 nm apart) and can be reached from Antigua on a longer passage. These islands are less visited by charter fleets, meaning quieter anchorages but fewer facilities. Sailing here is typically intermediate level – the winds are the same steady trades, but you’ll have stretches of open sea between islands (e.g. Antigua to Nevis is about 50 nm). Montserrat, with its active volcano, is an adventurous stop only for those confident in their skills; it lacks large harbours and conditions must be calm to visit. In summary, this central region is perfect for experienced holiday sailors: you should be comfortable with full-day passages and self-sufficient anchoring, but you’ll be rewarded with uncrowded bays and a touch of exploration off the main tourist track.

Guadeloupe, Les Saintes & Dominica: Lush and Remote

The southern end of the Leewards transitions to a more rugged sailing experience. Guadeloupe (part of France) is a large island with mountainous terrain, creating occasional wind acceleration zones and lee calms. It has several ports and marinas (such as Pointe-à-Pitre) and lovely offshore islets like Les Saintes, which offer mooring fields in picturesque settings. South of Guadeloupe lies Dominica, often considered the last of the Leewards (before the Windward Islands begin). Dominica is relatively undeveloped, with no marinas and only a few designated mooring areas (Portsmouth and Roseau). Sailing between Guadeloupe and Dominica or onward to Martinique involves longer open-water stretches with potential strong currents and choppier seas. This area is best for confident sailors – those with offshore sailing experience or who have crewed long passages. Novices would likely find the lack of support facilities challenging. However, for advanced crews, the payoff is huge: Dominica’s unspoilt nature (rainforests, waterfalls) and Guadeloupe’s French-Caribbean charm make these islands a delight. Sailors venturing here should be adept at navigation (especially if arriving at night or in squalls) and prepared for self-reliance. Many who cruise this region join rallies or buddy-boat with others for safety, but competent skippers will relish the freedom of these more remote cruising grounds.

Harbours and Mooring Styles in the Leewards

One of the pleasures of Caribbean sailing is the variety of harbours – from full-service marinas to quiet natural coves. In the Leewards you’ll encounter several anchoring and mooring styles:

Anchoring

Many bays allow anchoring and have good holding ground (often sand). Popular anchorages like Antigua’s Dickenson Bay or Marigot Bay in St. Martin have sandy bottoms ideal for anchoring. It’s common to anchor in 5–10 metres of water just off the reef or beach. Always check that your anchor is well set and not near coral heads or sea grass. Given the tidal range in this region is small (usually under 1 foot), you don’t need to worry much about big tidal swings, but do pay attention to depth under your keel, especially in Barbuda’s shallow lagoons or near reefs. Some anchorages can be deep close to shore (e.g. parts of St. Barths or Saba), so ensure you have enough chain rode for a secure scope. Good anchoring etiquette is essential: give other boats ample swinging room and avoid dropping anchor too close to a vessel on a mooring or anchor.

Mooring Buoys

Throughout the Leeward Islands, you’ll find mooring buoys installed in popular bays and marine parks. These mooring balls are a convenient way to secure your yacht without deploying an anchor, and they help protect coral from anchor damage. In the BVIs and USVI, moorings are very prevalent – you’ll see fields of white buoys in spots like the Baths at Virgin Gorda or Cane Garden Bay, typically available for a nightly fee. Further south, moorings are common in places like Gustavia Harbor (St. Barths), Les Saintes (Guadeloupe), and marine reserve areas. For example, in Gustavia there is a mooring field with both bow and stern attachments to keep boats from swinging in the tight harbour. When using moorings, inspect the line and buoy for damage as a precaution. Normally, you’ll pick up the buoy from the bow – having a crew member with a boat hook ready is useful. Note that moorings in high season can fill up by mid-afternoon in popular spots, so arriving early to secure one is wise. Each island authority or park may have its own fee system (some require paying ashore or to a patrol boat in the evening).

Marinas and Docking

Full-service marinas are available on most major islands, providing docks with water, electricity, fuel, and other amenities. Tortola (BVI), Sint Maarten (Dutch side), Antigua, St. Kitts, and Guadeloupe all have yacht harbours or marinas. Docking styles can vary: in many Caribbean marinas, you’ll either med-moor (stern-to docking) using a laid line or your anchor at the bow, or dock alongside if space permits. For instance, yachts in Antigua’s English Harbour (Nelson’s Dockyard) often med-moor to the historic quay. In St. Martin’s marinas, you may be directed to back in between finger piers. Be prepared with fenders and dock lines on both sides as you approach. Marina staff (dockhands) are usually on VHF channel 16 or a working channel to guide you in and assist with lines. When docking med-style, the typical procedure is to drop your anchor a short distance off the dock, then reverse in while paying out chain, and secure stern lines to the shore – this is a bit advanced, so don’t hesitate to request assistance if you’re new to it.

Local Mooring Customs

In some smaller island harbours, you might encounter informal mooring or docking arrangements. For example, off Nevis there are a series of mooring buoys set up by the local tourism authority for visiting yachts; no anchoring is allowed in certain areas to protect the seabed. In Dominica, enterprising locals maintain moorings in Prince Rupert Bay (Portsmouth) – they will often guide you to a mooring and later collect a fee, which also contributes to a security patrol for the anchorage. These scenarios are part of the local sailing culture – it’s customary to pay reasonable fees and perhaps tip if someone helped you. Always ensure any mooring you take is well-maintained; if unsure, anchoring at a safe distance might be better.

Chartering in the Leeward Islands

Chartering a yacht is one of the best ways to explore the Leewards, and there are plenty of options to suit your preferences and experience. Here’s what to consider when planning a charter in this region:

Charter Types

There are many charter options available but here are the most popular types. If you require a different type of charter, fill out our concierge form and we will discuss options with you.

Peak Seasons and Booking Tips

The timing of your charter will influence availability and cost. High season in the Leewards coincides with the northern hemisphere winter: from mid-December through April. The Christmas and New Year period is especially busy – popular boats and crewed yachts get booked out up to a year in advance for the holiday weeks, and prices are at their peak. During high season, you’ll enjoy fantastic weather but should expect higher marina fees and crowded anchorages in prime spots.

Shoulder season (May, June, and November) can be a sweet spot – slightly lower prices, fewer boats, and generally still decent weather (with a bit more chance of rain or the odd squall). Off-season (July to October) is hurricane season; many charter companies either close operations for part of this period or offer steep discounts with generous rebooking policies in case of a named storm. If you charter in these months, consider purchasing travel insurance that covers weather events, and plan a flexible itinerary (maybe stay around one main island with a secure marina nearby). You’ll find the islands much quieter in summer – which can be enjoyable – but always keep an eye on the tropical weather outlook.

Booking Tips

It’s wise to book well in advance for high season, especially if you have specific dates, need a larger yacht, or want a crewed charter with a particular crew. Early booking can sometimes fetch discounts or perks. Conversely, some late deals can be found in shoulder and low seasons. Work with a reputable charter company or broker, and make sure you understand the payment and cancellation terms. When booking, you’ll submit a sailing résumé or certificates (for bareboat) so the company is confident you’re qualified for the area. Also, clarify what’s included – typically the base price covers the yacht and its equipment; extras might include insurance waivers, fuel, water, park permits, and sometimes outboard fuel or snorkel gear. Many companies offer provisioning services where they can stock the boat with groceries for you – consider this if you want to save time at the start of your trip (more on provisioning later).

Certifications and Requirements to Charter

One common question is what qualifications are needed to charter a yacht in the Leeward Islands. The good news is that formal sailing licenses are generally not mandatory in the Caribbean, unlike in parts of Europe. Instead, charter companies focus on your experience. Here’s a breakdown:

• Experience Over Licenses: In most Leeward Islands locations, there is no legal requirement for a skipper to hold a certificate. Charter companies will ask for a sailing résumé or experience declaration from the lead charterer. They typically look for previous experience as skipper or first mate on a similar-sized vessel. For example, a company might expect that you have skippered a 35-40 ft boat on coastal trips if you are renting a 40 ft bareboat. Experience in tidal waters or at night is less crucial in this region, but heavy-weather experience is a plus. If your résumé is borderline, some companies may require you to hire a skipper for the first day or two as a check-out (or for the whole trip if they’re not confident).
• Sailing Certifications: While not required, having a recognized certification can strengthen your charter application and sometimes is encouraged. Certifications such as the RYA Day Skipper (or higher), the ASA Bareboat Cruising (ASA 104), or the International Certificate of Competence (ICC) are well-regarded. These can serve as proof of competency. Notably, in some countries these are legally required – for instance, European Union waters often require an ICC or national equivalent. But in the Leewards, charter firms generally just use them as evidence that you have received formal training. Bring any certificates or licenses with you on the trip, even if not asked in advance, because if you visit a French island (e.g. St. Martin or Guadeloupe), local authorities could ask for proof of competency or a VHF radio license during a routine check. It’s rare, but it’s better to have documentation on hand. Sunsail, for example, advises that no license is needed for Antigua & Barbuda, but they strongly recommend having your sailing certification handy in case you’re asked by officials.
• Differences by Company: Some charter companies have their own “level” rating for destinations. For instance, The Moorings classifies the BVIs as an easy-sailing area (often accessible to sailors with around 5 days of skippering experience), whereas St. Martin or St. Lucia are considered advanced areas requiring more miles under your belt. If you’re planning to charter in a more challenging Leeward area (like a one-way from St. Martin to Antigua, involving longer passages), expect the charter company to scrutinise your resume more carefully. They might want to see that you’ve handled similar open-water sails. In contrast, for a week in the sheltered BVIs, they might approve a less seasoned sailor, perhaps with just a couple of flotilla holidays and a competent crew. Always be honest about your experience; it’s about safety, not judgment. If you exaggerate and encounter trouble, it could endanger you and your crew.
• Crew Requirements: If you’re the primary skipper, it helps to have at least one other experienced crew member or co-skipper. Many companies actually require a second competent crew on board (not necessarily licensed, but someone who can take over in a pinch). This is particularly important for managing the boat in marinas or heavy weather. Make sure your crew is aware of basic tasks (anchoring, sail handling, navigation) or be ready to teach and delegate as needed.
• VHF and Local Regulations: A VHF radio operator’s license is generally not policed in the Caribbean for leisure yachts, but having one (e.g. the Short Range Certificate) is beneficial and sometimes required by European-flagged charter boats. Check the specifics if your charter contract mentions needing a licensed radio operator. Also, confirm any other local rules – for example, if you plan to fish, some islands require a fishing permit (like the BVI). These are not “sailing certifications” per se, but additional permissions that might be needed based on your activities.

Who Is the Leeward Islands Sailing Region Best Suited To?

With such a variety of conditions and destinations, the Leeward Islands truly have something for every type of sailor and are best suited to those who seek variety. The region can be as easy or as challenging as you choose to make it. It’s ideal for mixed-ability groups too – perhaps one skilled skipper and a bunch of friends who are learning; there will be safe harbours to practice sailing and also a few exhilarating passages to keep the skipper entertained. The key is planning: tailor your route and boat choice to your capabilities and goals. And remember, sailing is supposed to be fun! The Leewards, with their perfect mix of conditions, truly deliver fun in spades for anyone who loves the sea.

Practical Tips for a Smooth Sailing Trip

To round out your preparation, here are some hands-on practical tips and advice specific to sailing around the Leeward Islands. These cover the nitty-gritty details that can make your cruise safer and more enjoyable:

1. Provisioning and Supplies:

Plan your grocery and supply stops wisely. The larger islands (e.g. Tortola, St. Martin, Antigua, Guadeloupe) have well-stocked supermarkets where you can do a big provisioning run. If your charter starts at one of these, you can either pre-order provisions through the charter company or visit a supermarket upon arrival. French islands are known for excellent food shopping – in St. Martin or Guadeloupe, look for stores like Carrefour or U Express, where you can get French cheeses, wines, and fresh baguettes (a treat during your cruise!). In contrast, smaller islands (Anguilla, Barbuda, Nevis, Les Saintes) have only tiny groceries or local markets with limited selection, so don’t count on finding specialty items there. It’s best to stock up on staples (and your preferred snacks!) before leaving the big ports. That said, do try the local produce markets: islands like Antigua or Dominica have vibrant public markets with tropical fruits, veggies, and fish – great for fresh, organic additions to your stores. Remember to buy drinking water if you’re unsure about tank water taste; although most yachts have water tanks for washing and possibly drinking, many sailors use bottled water for drinking/cooking. Refilling water: Marinas and some beach facilities offer water fill-up for a fee. Be mindful of water usage (take “boat showers”, etc.) since water can be precious on small islands.

2. Fuel and Maintenance:

Fuel docks are found in major harbours (Road Town, Jolly Harbour, Simpson Bay, etc.). Even on a sailing yacht, you’ll likely need to top up diesel for your engine and petrol for the dinghy outboard at least once if on a longer trip. Try to refuel when you have the chance, even if tanks are half-full – some islands might have occasional fuel shortages or the one fuel station might be closed for a holiday when you swing by. Basic maintenance checks on your yacht should be done as you go: every morning do a quick engine fluid check and visual inspection (especially if you have long passages that day), and keep an eye on the battery charge levels if you’ve been at anchor for a while (you may need to run the engine or generator to charge batteries if you don’t have solar panels/wind generator). The warm climate means managing refrigeration is important – don’t overload the fridge so it can keep things cold, and be prepared to run the engine or generator a bit to maintain battery power for the fridge overnight if anchored out. Spare parts: charter boats come with basic spares (like impellers, filters). It’s good practice to ask at the briefing where these are and what the procedure is if something breaks. Larger charter companies have chase boats or partner services on various islands for support, but if you’re far out (say, in Dominica on a boat chartered from Antigua), you might need to troubleshoot yourself or with phone guidance. A well-charged toolkit of your own, plus multi-meters, tape, cable ties etc., can be very handy for minor fixes.

3. Navigation Tips:

While the Leewards are mostly line-of-sight navigation, don’t rely solely on electronics. Chartplotters and apps (Navionics, etc.) are extremely useful – ensure your charts for the area are updated – but also cross-reference with paper charts or cruising guides that point out hazards. Coral reefs and sand banks shift slightly over time; local knowledge via cruising guides (like the Doyle or Cruising Guide Publications guides for Leeward/Windward Islands) will mention if, for example, a channel buoy is missing or a reef extends further than charted. If you’re approaching a new anchorage, do so in daylight whenever possible, with the sun ideally behind you or high overhead – this helps you spot reefs by color (the water colour will go from deep blue to turquoise to brownish over reefs). Many Caribbean sailors use a lookout on the bow when entering a reef-strewn bay. Navigation marks in the region follow the IALA-B system in the US-influenced islands (like USVI) and IALA-A in the French islands – this mostly affects which side buoy is red vs green when entering. Just be attentive; most main entrances are well-marked (e.g., the buoy colours switch at the Dutch/French border in St. Martin’s lagoon!). A key tip: avoid night sailing in reef areas. If you must sail at night (perhaps on an offshore leg between islands), aim to arrive at the destination by morning when you have good light. Use radar and AIS (if equipped) at night to keep track of any squalls or ships; there are some inter-island ferries and cargo vessels that operate at night, though not many. Also, note that around the full moon, coral heads in shallow water might be visible even at night due to bright moonlight – but don’t bank on it; it’s just an enchanting sight if you happen to see it.

4. Anchoring Techniques:

We discussed anchoring etiquette, but technique is worth mentioning too. Caribbean waters can be deceptively deep right near shore, so if you anchor in 10m depth or more, let out plenty of scope (at least 5:1 scope of rode, more if winds are strong). Always snorkel over your anchor once set, if feasible, to ensure it’s properly dug in and not on rock. At night, the wind often dies down, then may swing around or a land breeze can blow, so your boat might lie differently – that’s why having ample swinging room is important. If you plan to go ashore and leave the boat, double-check the anchor before you go. In spots with strong currents or swell, consider a second anchor or a stern anchor to keep the boat aligned. For example, in some anchorages in St. Barts or Barbuda a swell can roll in and cause boats to rock uncomfortably side-on; dropping a small stern anchor to hold the bow into the swell can make for a more peaceful rest. Just remember to retrieve it! Speaking of retrieval, if your anchor gets stuck under a rock or old chain (there’s a lot of history under these waters), maneuver the boat to change the angle of pull, and use a trip line or ask a snorkeler to help if needed. Patience is key – yanking aggressively can do more harm (to your gear or the seabed).

5. Using the Dinghy:

Your dinghy (tender) is your lifeline to shore when anchored out, so treat it well. Always secure your dinghy with a good knot at docks or secure it on the beach by pulling it up and perhaps tying to a tree or using a dinghy anchor. Unfortunately, dinghy theft can occur in some crowded harbors (Theft is not rampant, but places like St. Martin or Antigua have occasional issues), so it’s wise to lock your dinghy to the dock with a cable lock if you’ll be away for long. At night, lift the dinghy out of the water on the davits or with a halyard if possible, or at least tie it with a short painter – this prevents both theft and the dinghy accidentally drifting off if a knot fails. When driving the dinghy, observe the no-wake zones; go slow near marinas and mooring areas to avoid rocking other boats. If you’re landing on a beach through surf, approach bow-on to the waves at a moderate speed, then kill the engine at the last moment and tilt it up to avoid prop damage as you run it up the sand (practice makes perfect). It helps to have one person hop out just before it touches to guide it in. For docking the dinghy in town, never tie up in a ferry’s spot or on a private dock without permission. Most harbors have designated dinghy docks – use them so you don’t inadvertently trespass or get in the way of commercial operations. And a safety note: night dinghy rides – always carry a flashlight or better yet a 360-degree white light on a pole when motoring at night so you’re visible. Wear the kill-cord lanyard on your wrist in case you fall overboard while driving. Lifejackets should be accessible; often people don’t wear them on short dinghy hops, but be extra cautious if it’s choppy or a long ride (like taking a dinghy from an anchorage to a dock a mile away – consider lifejackets then).

6. Weather and Communications:

Even though the weather is generally stable, always check the daily marine forecast. You can get VHF weather reports (some local radio stations or the NOAA weather on VHF in the USVI/BVI). Many sailors in the Leewards also use forecast apps like Windy or PredictWind nowadays, which can show the expected wind, wave, and weather patterns. If a stronger tropical wave or developing storm is forecast, adjust plans to stay in a safer harbour or marina. Communication-wise, mobile phone coverage is surprisingly good around inhabited islands. Your phone might roam between different networks as you pass from a French island (Digicel, Orange) to a Dutch or English territory. Roaming charges can add up, so check with your provider. You can buy local SIM cards (e.g., Flow or Digicel are common carriers) if staying long and needing data. VHF radio is the primary boat-to-boat and boat-to-shore communication for short range. Always monitor channel 16 when sailing. Many ports and marinas use specific working channels (like 68 or 69) for communications – this info is in cruising guides. For emergency, the U.S. Coast Guard has a presence in Puerto Rico and cooperates with regional authorities for search and rescue; in the far Leewards (e.g. near Dominica/Guadeloupe), the French CROSS system is in charge of SAR. In a serious emergency, a call on VHF 16 or activation of a PLB/EPIRB will bring help. It’s wise to have a handheld VHF in your dinghy or on your person if you go hiking inland on a sparsely populated island, in case you need to reach your boat or call for help once back at the shore.

7. Money Matters:

The Leeward Islands involve different currencies and costs. The US Dollar (USD) is widely used in the USVI, BVI, and also accepted in many other islands (even if they have their own currency). Euros (EUR) are used in the French territories (St. Martin French side, St. Barts, Guadeloupe) but they also usually accept USD (often at a set rate like 1 USD = 0.85 Euro in shops, which may not be the best rate). Eastern Caribbean Dollar (XCD) is the local currency of many independent islands (Antigua, St. Kitts, Dominica etc.), but again USD is often taken. It’s handy to have some local currency for small purchases, tips, or remote areas. ATMs are available on major islands so you can withdraw XCD or Euros as needed. Note that credit cards are widely used for marinas, restaurants, and provisioning in the bigger islands, but smaller beach bars or village grocery stores might be cash-only. Budget for certain fees: each country may have small charges on entry or exit (clearance fees, environment levies). The BVI, for example, charges cruising taxes per person per day. St. Barths charges a small fee to clear in and a nightly fee if you’re on their moorings or dock. These won’t break the bank but keep some cash set aside for officialdom.

8. Health and Safety:

The sun is intense in the Caribbean – bring plenty of high-SPF sunscreen and apply regularly (nothing ruins a sailing trip like a bad sunburn on day 1!). Hats, UV-protective clothing, and sunglasses are essential gear. Stay hydrated; sailing in the wind can mask dehydration. Mosquitoes can be a nuisance on some islands, especially if you go inland or in rainy season – have insect repellent and keep hatch screens closed at dusk if anchored near mangroves or on a very still night. As for safety, violent crime against yachters is rare in the Leewards, but petty theft happens, as mentioned. Aside from locking dinghies, lock your yacht when you go ashore (most have padlocks or just lock the companionway). Don’t leave valuable items in plain sight on deck at night in port. Use common sense as you would traveling anywhere – e.g., in larger towns like Philipsburg (St. Maarten) or late-night parties, keep an eye on your belongings. Many islands have local Coast Guard or marine police; their contact info is in cruising guides, but you likely won’t need it. If you go swimming off the boat, be aware of current and drift – especially if snorkeling near passes or points, use a dinghy driver or a float so you don’t get swept away. Also, a tip: shuffle your feet a bit when wading in sandy shallows to avoid surprising stingrays (they’ll dart off). And don’t touch or step on coral or sea urchins (for obvious reasons!).

Local Customs, Codes of Conduct, and Etiquette

Sailing in a new region isn’t just about the winds and waves – it’s also about respecting local rules and culture. The Leeward Islands, being divided among several nations and communities, have certain protocols and etiquette points that visiting sailors should be aware of. Adhering to these will ensure you have a warm welcome wherever you drop anchor.

• Customs & Immigration Procedures: Whenever you sail to a different island country, you must clear customs and immigration. This typically means upon arriving at an island (before you go ashore elsewhere), you should sail to the designated port of entry and follow the check-in process. For example, if you’re sailing from the BVIs to St. Martin, you’ll clear out of the BVIs (exit paperwork) at a BVI port, then sail to (say) Marigot on the French side of St. Martin to clear into the new country. Ports of entry are usually main harbours or marinas – examples include Road Town (Tortola), Gustavia (St. Barths), St. John’s (Antigua), Basseterre (St. Kitts), Deshaies or Pointe-à-Pitre (Guadeloupe), and Roseau/Portsmouth (Dominica). The process generally involves filling out forms with crew/passport details and the boat’s information, presenting passports, and paying any relevant fees or cruising permits. Fly the yellow “Q” (quarantine) flag on your starboard spreader as you enter a new country’s waters; this signals that you need to clear in. Once formalities are done, you can take down the Q flag and hoist the courtesy flag of the country you are visiting (usually on the starboard spreader). Courtesy flags (small national flags of the host country) are a sign of respect and almost all yachts do this – you’ll want to have a set of courtesy flags for the islands you plan to visit (many chandleries sell a Leeward Islands flag pack). When leaving a country, you often need to officially clear out as well. Officers in these islands are used to yachties and the process is usually straightforward and friendly as long as you arrive during business hours (and not during lunch break, when offices might close!). Dress smartly (at least wear a shirt and shorts, not just swimwear) when dealing with officials, and be patient and courteous.
• Environmental and Marine Conduct: The islands are beautiful and largely well-preserved, and local authorities expect sailors to help keep them that way. Follow any rules about marine protected areas: if an area is marked as a nature reserve (like the coral reefs around Saba or the marine park in the BVI), make sure to use park moorings and refrain from anchoring on coral or damaging the reef. Many islands ban the use of holding tank discharge in nearshore waters – so avoid pumping out your waste tanks in any anchorage or swimming area (do it offshore in open deep water if needed, or use pump-out facilities where available). Avoid throwing any trash overboard; stow it and dispose of it in port properly (recycling is limited in some places, but do use it where available, e.g., St. Barts has recycling bins for yachts). It’s also illegal in many islands to fish or collect conchs/lobsters without a license – if you plan to fish, check the rules (BVI, for instance, requires a fishing permit for visitors, and no spearfishing is allowed). Essentially, treat the sea and the island environments with care: “leave no trace” when you depart an anchorage. Simple actions like picking up any floating litter you see or using eco-friendly sunscreen (to protect coral from chemicals) go a long way. Islanders are very tied to the sea; showing you respect their natural resources will win you friends.
• Anchoring and Mooring Etiquette: As mentioned earlier, give other boats space when anchoring. It’s bad form to squeeze in so close that there’s a risk of collision if the wind shifts. If a bay is very crowded, consider an alternative spot rather than forcing your way in. When on a mooring, don’t assume you can raft up (tie two boats to one mooring) – this is generally discouraged unless explicitly permitted by the mooring owner. Keep music and noise at reasonable levels, especially at night. Many people come to these bays for peace – loud partying into the night can disturb others (with a few exceptions, such as certain known party spots where everyone is in on the fun, like Foxy’s in Jost Van Dyke on New Year’s Eve!). Observe any local rules like no-wake zones for dinghies in harbors. Also, if you have a generator on your yacht, be mindful of when you run it – nobody likes exhaust fumes wafting over them during a sunset cocktail hour. A good practice is to run generators only during the day or early evening, and never late at night.
• Local Cultural Customs: The Leewards encompass different cultures and it’s polite to adapt accordingly. On the francophone islands (St. Martin’s French side, St. Barts, Guadeloupe), a friendly “Bonjour” (by day) or “Bon soir” (evening) when greeting locals goes a long way, even if you aren’t fluent in French. In more laid-back islands like Nevis or Dominica, people tend to greet others warmly – it’s common to say good morning/afternoon to strangers. So don’t be shy; a pleasant greeting or chat with a local vendor or fisherman can lead to great recommendations for your visit. Dress codes on shore are casual, but note that wearing only swimwear in town is usually frowned upon; throw on a cover-up or shirt when off the beach. When visiting churches, villages, or attending cultural events, modest attire is appreciated. Another custom: time moves slower in the islands. Don’t expect swift service at a restaurant or a dock – things happen on “island time”. Being patient and easygoing rather than pushing to stick to a strict timetable will make your interactions more enjoyable.
• Sailing and Right-of-Way: Standard maritime rules apply in the Leewards. Power gives way to sail (in general), but be mindful in busy channels (like Simpson Bay or near ferry ports) – ferries and commercial vessels may assume right-of-way due to their schedules and constraints. Keep a VHF tuned to channel 16 for any security calls (like large vessels announcing channel transits). Around dive sites, you’ll see dive boats flying the red-and-white diver down flag; give them wide berth and slow down to avoid endangering divers. If you’re sailing through a narrow cut or reef pass (for example, through the reefs of Barbuda or into the lagoon in St. Martin), announce your approach on VHF if it’s commonly used, or at least proceed with caution and a lookout.
• Interacting with “Boat Boys” and Vendors: In a few islands, particularly the less-developed ones like Dominica or parts of St. Kitts, you might be approached by local entrepreneurs in small boats as you anchor. They may offer services like water taxi rides, island tours, fresh fruit, or help with moorings. These individuals (often nicknamed “boat boys”, though they can be older men) can actually be quite helpful – for example, in Dominica the PAYS organisation members help yachties and provide security. The etiquette here is to be polite: if you need their services, negotiate a fair price (ask for a rate beforehand to avoid surprises), and if you don’t, a simple “No thank you, maybe later” will do. Most are not overly pushy if treated with respect. It’s also customary to tip for good service – e.g., if someone helps you tie a mooring and perhaps brings bread in the morning, a few extra EC dollars as a tip is appreciated.

FAQs – Common Questions from Sailors

Below are some frequently asked questions about sailing the Leeward Islands, with concise answers to clear up any remaining doubts:

Q: When is the best time of year to sail in the Leeward Islands?
A: The prime time is during the dry season from December to April. This period offers steady trade winds, minimal rain, and lots of social activity among cruising boats. It’s also peak tourist season, meaning vibrant island events but also more crowds. If you prefer slightly quieter conditions, consider the shoulder months of May or November, which still have decent weather. Try to avoid late summer (August–September), as this is peak hurricane season and many charter companies pause operations then. If sailing in summer, early July can still be nice – just be aware of increased humidity and the need to watch weather reports.

Q: Is it safe to sail during hurricane season at all?
A: Sailing in hurricane season (June–November) carries risks, but it’s not impossible with caution. Many experienced cruisers still roam the Caribbean in summer but have a strict eye on forecasts and typically a planned safe haven (like a hurricane hole or a quick haul-out plan) if a storm threatens. If you’re chartering, check with the company – some offer charters in summer with a clause that if a named storm is approaching, you must return the boat to base (or they’ll direct you where to go). Insurance policies often have exclusions during this period. In short, yes, it’s possible but you need to be vigilant and flexible. The safer approach if you want a summer sail is to go early in the season (June or early July) or late (October), and avoid the heart of August–September.

Q: Do I need a visa to visit different islands while sailing?
A: It depends on your nationality and the islands in question. The Leewards are governed by different countries: for instance, the USVI are U.S. territory (so U.S. entry requirements apply), the BVI is British (with its own entry rules), St. Martin/St. Barths/Guadeloupe are French (EU) territories, and other islands are independent nations (Antigua & Barbuda, St. Kitts & Nevis, Dominica, etc.) each with their own immigration rules. Many nationalities (US, Canadian, EU, British, etc.) get visa-free entry or a visa-on-arrival stamp in most of these places for short stays. However, if you require a visa for, say, the Schengen area (for the French islands) or for the US (for USVI), you’ll need to obtain those in advance. As the skipper, it’s your responsibility to ensure all crew have the right to enter the places on your itinerary. Check each destination’s official government website or consult a visa agent. Practically, in the yachting context, officials often just stamp passports at each stop. One helpful system in the Eastern Caribbean is SeaClear / SailClear (used by some islands like Antigua, St. Kitts, and others) where you can pre-enter crew info online to speed up clearance. Always travel with your passports (and any necessary visas) and be prepared to show return or onward travel plans if asked (though it’s rarely asked of yacht crews).

Q: What kind of sailing itinerary is possible in one or two weeks?
A: In one week, it’s best to focus on a small region: for example, exploring the BVIs alone (one-week itinerary could hit Tortola, Norman Island, Jost Van Dyke, Virgin Gorda, etc.), or St. Martin and its neighbors (e.g., St. Martin -> Anguilla -> St. Barths and back). In two weeks, you can be more ambitious, like a one-way from Antigua to St. Martin (including Barbuda, St. Kitts/Nevis, Statia, Saba, St. Barths, etc.), or even St. Martin to Guadeloupe and back (covering St. Barths, Nevis, Antigua, Guadeloupe, Les Saintes, etc.). Distances aren’t huge between each island, but a multi-island trip means more time spent on formalities and sailing, and less time relaxing at each spot. So plan according to whether you prefer a relaxed cruise (fewer islands, more time at each) or an exploration cruise (hopping to a new island almost daily). Both styles are rewarding. Just avoid overstuffing your itinerary – leaving some buffer time for weather or whimsy is wise. Many people find they only manage to see half the places they planned, but that’s okay, it’s an excuse to come back!

Q: Are the Leeward Islands suitable for absolute beginners to sailing?
A: As a crew member or on a skippered trip, absolutely yes. As a bareboat skipper, if you’re an absolute beginner, you should not be skippering yet – but you could join a training flotilla or take a sailing course in the region. The BVIs are often recommended as a place for newly qualified sailors to do their first bareboat charter (with perhaps an instructor or skipper for the first day or two). If you have zero sailing experience, consider joining a crewed charter or a sailing school. There are sailing school vacations, even some ASA courses that run in the Leewards where you learn while cruising around. In summary, beginners can enjoy sailing here under guidance, and the learning curve will be enjoyable because conditions are mostly forgiving. Just don’t jump in over your head – safety first.

Q: What if we encounter very bad weather or an emergency?
A: For regular squalls or strong winds, the best action is to seek shelter in a safe anchorage or marina. The Leewards have plenty of natural harbours. If a surprise system comes (say a tropical storm not forecast), get to the closest well-protected bay, set multiple anchors or moorings, and ride it out. All charter yachts carry VHF radios – you can hail the local coast guard or ask other boats for help if needed. In a dire medical emergency, use the VHF or a sat phone (if offshore) to call for assistance. Many islands have heli evac or marine patrol capabilities. Know the locations of clinics or hospitals on the islands you visit (e.g., there are hospitals in Tortola, St. Thomas, St. Martin, Antigua, etc.). Carry a good first aid kit – often the biggest “emergencies” are fish hook cuts, coral scrapes, or seasickness, which you can handle on board. For life-threatening situations (rare), trigger your EPIRB or PLB if you have one, which will alert regional rescue. It’s also wise to have travel insurance that covers medical evacuation from a boat, just in case. But rest assured, you are not venturing into the wild unknown – the Leewards have infrastructure and other boaters around. Help is usually not far away.

Q: How much does it cost to moor or anchor in these islands?
A: Anchoring is free virtually everywhere (assuming you’re not in a restricted zone). Mooring buoys typically have a nightly fee. In the BVIs, moorings often cost around $30 per night (it might be $25–$40 depending on the location and the managing company). In St. John, USVI, there’s a system where you pay $26 for a mooring (as of recently) via an app or self-service. In the French islands like Les Saintes or St. Barts, expect fees in Euros, roughly €10–€20 a night for a mooring (and in Gustavia, St. Barts, they’ll charge more in high season). Some marine reserves have moorings that are free for daytime use (like the diving buoys in Saba or the National Park moorings in the BVIs) but then you either can’t stay at night or you pay if you do. Marinas vary widely in cost: the fancy marina in Gustavia or Marina Fort Louis in St. Martin can be €1-2 per foot per night or more in high season (plus electricity/water); simpler marinas like Nevis or small town quays might charge very little. Budget for moorings if you plan to use them frequently – a week in the BVIs solely on moorings could add a couple hundred dollars. Many charter companies let you pre-book a mooring package or will advise which app to use for booking moorings (like BoatyBall in the BVIs for certain locations). Overall, these costs are modest in the scheme of your trip, but it’s good to have cash on hand to pay mooring fee collectors who come by in the evening.

Q: Can we drink the water from the boat’s tanks?
A: If your charter company says the water is potable and the tanks are clean, yes you can. They usually fill up with municipal or filtered water at base. However, many sailors prefer the taste and assurance of bottled water for drinking and cooking. The tank water is fine for washing, cleaning, and making hot beverages (if boiled). In some places, water has a bit of a chlorine taste or slight coloration, so crews opt to use bottled jugs for direct consumption. It’s really personal preference and sensitive stomachs. A nice middle ground is to use tank water but through a portable filter (like a carbon filter jug) for drinking. This reduces plastic waste and is convenient. Remember, staying hydrated is crucial in the tropical heat, so whichever water you choose, drink plenty.

Q: Are there any dangerous animals or marine life to worry about?
A: Generally, the Leeward Islands are free of anything extremely dangerous. There are no coral snakes or such on these islands. Mosquitoes can carry diseases (dengue, etc.), so use repellent to avoid bites. In the water, sharks are not a big concern for swimmers – reef sharks and nurse sharks are around and usually harmless if not provoked; there’s virtually no history of shark incidents in the swimming areas. Watch out for jellyfish or fire coral when snorkeling; some seasons have more jellies (like bits of thimble jellyfish larvae that can cause “sea itch”). Wearing a rash guard or thin wetsuit while snorkeling protects against sun and any stinging plankton. Sea urchins (spiky) lurk on rocks; wear water shoes if stepping in shallow rocky areas. Also be cautious of lionfish when diving or snorkeling – they have venomous spines (and are an invasive species often culled by divers). They won’t attack, but don’t touch one accidentally. On land, sand flies/no-see-ums can bite at dawn/dusk on beaches – again, repellent helps. One thing to note: some fruits or plants might irritate skin (e.g., manchineel trees found near beaches can cause rash if touched) – but those are usually marked or known by locals. In summary, the wildlife is more friend than foe. Take normal care and you’ll be fine. If you’re allergic to bee stings, carry an Epipen because there are bees/wasps around like anywhere.

Q: What’s the connectivity like (Wi-Fi, cell service)?
A: Connectivity is improving all the time. Most populated islands have 3G/4G mobile coverage around their coasts. You might lose signal in open water between islands, but near shore you can often get data on your phone. As mentioned, SIM cards from regional providers can give you data plans (e.g., Digicel’s Caribbean plan or Flow’s packages cover multiple islands). Some charter boats now come equipped with Wi-Fi routers – either GSM based (so you’d need to get a data SIM or the company provides it for a fee) or satellite based (which is usually slow and costly, used more for emergency emails). Marinas and cafes often have Wi-Fi; just be prepared that it may not be lightning fast, especially if many people are on it. If you need to do remote work, best to schedule that when you’re docked in, say, St. Martin or Antigua where infrastructure is better, rather than when you’re anchored off a tiny islet. But for checking weather or sending messages, your cell phone will suffice in most anchorages. Some cruisers also use devices like the Iridium Go (satellite) for backup weather and messaging when out of cell range. For a leisure charter, you likely won’t need that. Unplugging can be nice! Do inform close family or friends of your approximate route and that you might be offline for stretches, so they don’t worry if you don’t reply instantly.

These FAQs address the main concerns sailors have before setting off. If you have a question that’s not covered here, chances are a fellow sailor on a forum or a local charter company has the answer. Preparation is important, but once you’re there, you’ll find the sailing community and island residents are very welcoming and helpful. So, cast off the lines with confidence and get ready to enjoy the Leeward Islands!

References

• The Guardian – Weatherwatch: The climate of the Leeward Islands theguardian.com
• Adventure Life – Leeward Islands Weather (Climate summary for the Leewards) adventure-life.com
• The Moorings – BVI Yacht Charters (Experience Level 1) moorings.com
• The Moorings – St. Martin Yacht Charters (Experience Level 3) moorings.com
• The Moorings – Resume & Requirements (Sailing experience levels and requirements)moorings.commoorings.com
• Sunsail – Antigua Charter – Useful Information (Licensing advice) sunsail.com
• Ed Hamilton & Co. – “Am I Qualified to Charter a Bareboat?” (Charter qualifications in Caribbean) ed-hamilton.com
• Broadreach Blog – Caribbean Island Chains Guide (Leewards highlights and best-for info) gobroadreach.com
• Marinalife – Cruising the Leeward Islands (Harbour mooring example in St. Barts) marinalife.com
• SailChecker – Top 10 Islands for Caribbean Bareboat (Wind info and license note) sailchecker.com