The Cyclades are a picturesque archipelago in the central Aegean Sea, famous for whitewashed villages, blue-domed churches, and vibrant culture. But sailing in the Cyclades is as challenging as it is rewarding.

Unlike the sheltered Saronic Gulf near Athens, the Cyclades’ open waters and strong summer winds offer a more adventurous experience. These islands lie in the path of the Meltemi – a powerful seasonal north wind – making planning and seamanship crucial.

This guide provides an in-depth look at wind patterns, safe harbours, local regulations, mooring techniques, weather quirks, charter options, required qualifications, skill levels, suggested routes, safety tips, and seasonal advice to help you sail the Cyclades with confidence.

Wind Patterns and Climate

The Meltemi Wind – the defining feature of Cyclades sailing – is a dry northerly wind prevailing from May to September and peaking from mid-July to mid-August. It’s formed by a high-pressure system over the Balkans meeting low pressure over Turkey (Asia Minor).

During summer it can blow for days at a time, often Force 5–7 on the Beaufort scale with frequent gusts reaching Force 8–9 (gale force). In practical terms, a forecast of 15–20 knot winds might mean gusts over 30 knots in the Cyclades.

The Meltemi is usually accompanied by clear skies, low humidity, and excellent visibility – a true “fair-weather” wind. But its strength can kick up sudden “white squalls” (violent gusts from a clear sky that froth the sea white) when blowing hard.

After blowing for consecutive days, the Meltemi also creates a rough sea state, with 2–5 m waves often coming in sets of three from multiple directions, which can make passages very bumpy.

Daily & Seasonal Variations

A Meltemi pattern typically lasts a few days on then a few days off. It tends to peak during the afternoon heat (as land warms and draws the wind) and ease overnight. Early mornings often have lighter winds – a useful window if you need to sail upwind. After sunset the wind usually calms, making evenings and nights relatively tranquil.

In spring and autumn, winds are generally milder and less predictable, with occasional low-pressure storms or southerly winds instead of the steady Meltemi. Winter (November–March) brings very unsettled weather – gales from various directions (Aegean winter storms can reach Force 8–9) and frequent rain.

The best sailing weather in the Cyclades is usually in late spring (May–June) and early fall (September–early October) when the Meltemi is weaker or intermittent and conditions are pleasantly warm. July and August offer hot, dry weather but the trade-off is the Meltemi blowing at full strength with frequent gale-force days.

Local Wind Effects

The complex topography of the Cyclades – dozens of rocky, mountainous islands – means wind conditions can change over short distances. Islands can create wind shadows, acceleration zones, and katabatic gusts:

Funnelling and Acceleration: The Meltemi gets channeled through gaps and valleys, so wind may accelerate like a jet through straits. For example, narrow passages (such as between Andros and the tip of Evia at Kafireas Strait) are notorious for amplified winds and rough seas. These areas can be significantly windier than open-sea forecasts suggest.
Leeward Gusts (Wind Shadow Turbulence): High islands provide a wind shadow directly behind them, but around their edges and on the leeward side, the wind often rejoins violently as gusts. As the Meltemi flows around a big island, it “bends” and can actually increase in speed to get past the obstruction. The rule of thumb is: the higher the island, the stronger and more frequent the gusts on its leeward side. Sailors should be prepared for sudden forceful blasts even in sunny, otherwise calm-looking lees – these are the clear-sky squalls that can catch you off guard.
Katabatic Winds: At night, the islands cool and dense air can drain downhill. In some spots this creates katabatic winds that blow offshore in the late night or early morning. These are usually modest in the Cyclades compared to the Meltemi, but in certain places (like the high cliffs of Amorgos) strong gusts tumble down cliffs, hitting boats below without warning.
Geographical Wind Shifts: Note that the Meltemi’s direction can vary across the region: in the western Cyclades it often blows NE, while in the eastern Cyclades it’s more N or NW. Around some islands, a north wind may feel northwest or even west due to bending. Always check local forecasts for wind direction as well as speed.

Practical Tips – Weather

Smart Cyclades sailing means respecting the Meltemi. Plan routes that work with the wind when possible and be ready to adjust plans if a gale is forecast. Pay close attention to forecasts and learn the signs of a coming Meltemi: rising barometric pressure, a sudden drop in humidity (your decks stay dry in the morning), and banks of high altocumulus clouds or lens-shaped orographic clouds over island peaks a day prior.

Should a strong Meltemi set in, don’t hesitate to seek shelter in a safe harbour for a day or two – even ferries will cancel service in extreme wind, so there’s no shame in waiting it out. With good planning and a keen weather eye, the Meltemi can become a useful ally (providing fast, exhilarating sailing on passages) rather than a hazard.

Harbours and Anchorages in the Cyclades

Despite the challenging winds, the Cyclades offer many harbours and anchorages that provide welcome shelter. Most inhabited islands have a main port or marina, and there are countless coves to anchor in. Below are some key harbours and recommended anchorages – including their facilities and wind protection characteristics – that sailors should know:

Parikia (Paros) – The primary port of Paros, a natural harbour used since antiquity. It offers many berths on the quay, with access to electricity, water, fuel, and provisions in town. Parikia is moderately sheltered from the Meltemi (which blows from the north); a long breakwater protects the inner harbour, though a strong north wind can send some chop into the bay. It’s a convenient stop for resupply and shore leave, with plenty of tavernas and shops by the waterfront.
Naoussa (Paros) – A charming fishing-port-turned-marina on the northern tip of Paros. Naoussa is often called one of the most picturesque ports in Greece. It has a small marina basin and anchorage just outside. The marina serves as a shelter from strong winds for yachts, making it a popular refuge when the Meltemi howls. Space is limited (especially in peak season), but the setting is idyllic – Venetian ruins at the harbour mouth and seafood restaurants lining the quays.
Naxos Town (Naxos) – The largest Cycladic island’s main harbour, Naxos has a ferry pier and a yacht quay inside a substantial breakwater. It offers water, electricity, and some repairs, plus easy access to the lively Chora (town). The harbour is open to the north but partially shielded by the breakwater – expect strong Meltemi days to send some swell into the bay. Holding is generally good in sand if anchoring off. Naxos is a must-visit for its blend of beaches, history, and local culture.
Mykonos – Ornos Bay – Mykonos has a new marina (at Tourlos) that provides berths, but it’s notably prone to surge in northerlies and often crowded. Many sailors prefer Ornos Bay, a broad cove on Mykonos’ south side. Ornos offers excellent shelter from all wind directions, including full protection from the north. Yachts can anchor in sand with good holding, and the bay is ringed with beach cafes and provisions. It does get very busy with yachts in summer (arrive early to find space), but it’s a reliable hideaway when the north wind makes Mykonos’ north coast (and party beaches) untenable.
Syros – Ermoupoli – The capital of the Cyclades, Syros has a large commercial harbour at Ermoupoli which doubles as a yachting stop. As a port of entry with customs, it’s well-equipped – marina berths, fuel, water, and full services are available, and it’s one of the few islands with extensive repair facilities. Ermoupoli lies on the island’s east, giving good shelter from the Meltemi (N-NW). With its grand architecture and shipyard history, Syros makes an interesting urban contrast during a cruising itinerary.
Serifos – Livadi – Serifos’s main harbour, Livadi, is a wide bay with a new marina/harbour mole. The bay faces south, so it is well-protected from the prevailing north winds (very calm in Meltemi conditions). The small marina has a few mooring spots for yachts and offers basic provisions and water. Livadi’s long sandy beach (Avlomonas) and the steep path up to Serifos’s hilltop Chora are highlights. Note: In strong southerly (rare in summer), Livadi would be exposed, but during summer Meltemi it’s one of the safest stops.
Sifnos – Vathy Bay – On Sifnos’ southwest coast lies Vathy (Vathi) Bay, an enclosed inlet often cited as a textbook Meltemi refuge. A narrow entrance opens into a nearly land-locked bay with sandy bottom. It provides “superb shelter from prevailing winds”, making it an ideal anchorage to wait out a blow. Ashore are a couple of tavernas under tamarisk trees and a tiny village – a tranquil, family-friendly spot. Depths are shallow in parts, so larger yachts anchor toward the centre. If you need utter peace and protection, Vathy is a gem.
Milos – Adamas Port – Milos boasts a huge natural harbour – the island is a volcano with a water-filled caldera bay. Adamas (Adamantas) is the port town inside this bay. It is one of the safest harbours in the Cyclades, offering excellent shelter from the wind in almost all conditions. Yachts moor Mediterranean-style at the quay or anchor further out. Facilities include water, fuel by mini-tanker, plenty of restaurants, shops, banks and even an ATM. Adamas is a common stop to explore Milos’s famous beaches and geological wonders. Even in a gale, the waters inside remain relatively calm (just watch gusts at the hill gaps).
Ios – Mylopotas & Ormos – Ios has two notable stops. Ormos Iou (Ios Harbor) on the west side is a decent harbour with a long quay inside a bay; it’s somewhat sheltered from Meltemi by surrounding hills, though strong winds can still send bullets into the bay. It’s convenient for visiting Ios town (known for nightlife). Further south, Mylopotas Bay offers a different vibe – it’s a popular beach bay on Ios that also serves as a sheltered anchorage from the Meltemi. Mylopotas faces south and is ringed by a golden beach and resorts. In summer it’s busy with beachgoers, but cruisers stop here to enjoy a calm night when the north wind is howling offshore. Holding is good in sand around 5–8 m depth.
Amorgos – Katapola – Amorgos, on the eastern edge of the Cyclades, has two harbours. Katapola, on the central west coast, is the main one and a popular marina/anchorage combo. It’s a scenic bay with three little villages around it. The holding is good and it’s reasonably sheltered from Meltemi (open NW but Amorgos’s high terrain blocks much of the force). Yachts med-moor at the quay or anchor in the bay. Katapola has a few tavernas and small shops, and even some ancient ruins above the port. It’s a peaceful stop before or after tackling the heavier winds around Amorgos’s notorious cliffs (the northeastern coast, as noted, can send violent gusts). The island’s second harbour, Aegiali, is on the north coast and more exposed to N winds – Katapola is usually the better bet in Meltemi season.
Kythnos – Loutrá – On Kythnos (one of the closer Cyclades to Athens), Loutrá is a small fishing harbour turned yacht haven on the NE coast. It is known as a safe haven for mariners, with a municipal marina of 20+ berths. It’s well sheltered from the Meltemi (which blows offshore here) and even offers hot springs near the shore. Loutrá can accommodate yachts up to ~15 m and even has electricity, water, and a few tavernas nearby. This is often the first or last port of call when doing an Athens–Cyclades loop, providing a gentle re-entry to civilisation. (Another Kythnos highlight is Kolona Bay on the west side – a double-sandbar anchorage that’s very scenic and relatively protected from northerlies – but it has no facilities onshore, so come prepared.)
Santorini (Thira) – The spectacular volcanic island of Santorini is a tricky place for sailors. The famous caldera (the drowned crater) is very deep and only suitable for short stops or specialty moorings – anchoring in 50+ meters with steep sides is not practical for most. The best option is the small marina at Vlychada on Santorini’s south coast. Vlychada is a narrow, dredged harbour that offers decent shelter (although strong SW winds or swells can make the entrance challenging). It has limited berths and fills quickly in summer. Basic water and electricity are available. Many sailors actually leave the boat in Ios or Paros and visit Santorini by ferry due to the limited mooring options. If you do sail here, plan carefully and avoid the caldera in strong winds – katabatic gusts and poor holding have caused many an accident for the unwary.

Shelter & Holding

When choosing an anchorage in the Cyclades, always consider the Meltemi exposure. South-facing bays (lee of the north wind) tend to be calm in summer – e.g. Vathy (Sifnos), Mylopotas (Ios), Psili Ammos (Serifos’s east coast, gorgeous anchorage if calm).

Ensure your anchorage has good holding ground (sand or mud is ideal; weed or rock can be problematic). Many Cycladic bays have sandy patches – aim for those and set your anchor firmly. The wind often swings northwest at night, so check that a slight shift won’t put you on a lee shore.

Generally, the Cyclades offer ample anchoring opportunities, but in July/August they can be very crowded with charter boats. By early afternoon, the best spots in a bay or harbour may be taken, so it’s wise to arrive early to secure a safe anchorage or quay spot.

Recommended Routes and Itineraries

The Cyclades Islands offer countless itinerary possibilities. Your route will depend on wind, skill, and how long you have. Below are a few popular sailing routes with notes on difficulty, must-see stops, and seasonal suitability. Assume a starting base either in Athens (Lavrio) or one of the larger islands like Paros or Mykonos, as these are common charter pickup points.

1. Western Cyclades Loop (1 week) – Lavrio – Kea – Kythnos – Serifos – Sifnos – Milos (and back via Kimolos/Sifnos). This route covers the northwestern Cyclades, which are an excellent choice for first-time Cyclades sailors. Kea (1st stop from Athens) has a safe harbor at Korissia and ancient ruins to explore. Next Kythnos offers Loutrá (hot springs and a marina) or Kolona Bay (a stunning double beach anchorage). Sail on to Serifos (Livadi port) for a charming harbor and hike to a hilltop Chora. Sifnos is next – either Kamares port or the calm Vathy Bay. Finally, Milos with its giant sheltered bay and incredible geology (try anchoring at Kleftiko’s sea caves if weather allows). Milos’s Adamas port is a good turnaround point. This itinerary features moderate sailing legs (~20-30 nm or less between stops) and plenty of bailout options. It’s relatively sheltered from big swell, and you’ll get a taste of Cycladic culture on each island. It’s manageable in Meltemi if you go clockwise (so the longest leg, back from Milos towards Kea/Lavrion, can be a reach or downwind). In spring or fall, any direction works. Difficulty: Moderate (Intermediate) – mostly downwind sailing in summer, and multiple safe harbors available. Highlights include ancient Kea, Serifos’s Psili Ammos beach, and Milos’s moon-like Sarakiniko cove.
2. Central Cyclades Highlights (1 week) – Paros – Naxos – Small Cyclades (Koufonisia) – Amorgos – Antiparos – Paros. If you start your charter in Paros (Parikia or Naoussa), this route hits marquee destinations. From Paros, a short hop east to Naxos, the largest Cyclade, known for its Portara ruins and lively town – anchor or dock in Naxos Marina (can be gusty). Then head to the Small Cyclades: tiny Koufonisia and neighboring Schinoussa or Iraklia offer tranquil villages and crystal-clear bays perfect for a calm anchorage. They’re a great respite from the crowds and wind, as these smaller isles are low-lying and somewhat sheltered. Next, sail to Amorgos (likely Katapola port) to see the famous clifftop monastery and enjoy the island’s rustic beauty. Start turning back westward with a stop at perhaps Iraklia or Antiparos on the return. Antiparos has a lovely anchorage near Despotiko island and a fun cave to visit. Finally end back at Paros. This Central Cyclades route takes you through the heart of the archipelago, mixing busier islands with remote ones. Difficulty: Moderate to High. Some legs (Naxos to Amorgos) are longer (35+ nm) and can be very windy – plan those for a calmer day or motor if needed. The Small Cyclades are relatively easy, but open crossings to Amorgos or back to Paros can be challenging in Meltemi. Best in June or September, or pick your weather windows carefully in July/August. Must-visits include Naxos’s old town and beaches, Koufonisia’s turquoise lagoons, and Amorgos’s Hozoviotissa Monastery clinging to the cliff.
3. Southern “Grand Cyclades” Route (10-14 days) – Syros – Mykonos – Delos – Ios – Santorini – Folegandros – Sifnos – Syros. This ambitious itinerary is ideal for more experienced sailors seeking to see the famous southern Cyclades. Starting at Syros (a central location with an easy ferry or flight from Athens), you sail to Mykonos for a taste of its nightlife and Mykonos windmills. Nearby Delos (a short hop) is a must-stop during daytime – it’s an uninhabited island filled with ancient ruins (no overnight mooring allowed, but a daytime anchorage off the sacred harbour is feasible in settled weather). From Mykonos or nearby, you’d likely sail southward (with Meltemi behind you) past Paros/Naxos to Ios. Ios has fun beaches and a youthful vibe. Next, the crown jewel: Santorini – approach from the north for a dramatic entrance into the caldera if conditions permit. Given limited mooring, many will stay only a day or two; you might anchor off Thirassia island or take a buoy if available, or go to Vlychada marina on the outside. After Santorini, head to Folegandros, a lesser-known gem with high cliffs and a serene atmosphere. Its small port (Karavostasis) and gorgeous clifftop town are a highlight. Then route back via Sifnos or Serifos to Syros (or direct to Syros if time). This route hits big names (Mykonos, Santorini) and quieter beauties. Difficulty: High (Advanced) – recommended only when Meltemi is mild or if you have time to wait out blows. The leg from Mykonos toward Ios/Santorini is long and can be rough (you might break it up via Naxos or Paros if needed). Santorini itself requires expertise to approach safely. This is best done in late spring or early autumn, or by very competent crews in summer. The payoff is seeing the full spectrum of Cyclades, from cosmopolitan to untouched. Don’t miss sunset in Oia (Santorini), the ancient theater of Delos, and Folegandros’s cliffside church at sunset.
4. The Little Loop (5 days) – Mykonos – Paros – Antiparos – Serifos – Kythnos. For those with less than a week, one could fly to Mykonos, charter from there, then sail a loop ending closer to Athens. For instance: Mykonos to Paros Naoussa (easy reach), then to Antiparos (lovely anchorage at Despotiko’s bay), then a longer leg to Serifos (Livadi), then Kythnos Kolona or Loutra, and end in Lavrio on the mainland. This one-way or semi-linear route is commonly used by charter companies (they might allow drop-off at a different base). Difficulty: moderate, with the long Mykonos->Serifos stretch being the most exposed. It balances famous spots (Mykonos) with peaceful ones (Kolona double beach in Kythnos).

These are just a few ideas – the Cyclades are highly “mix-and-match.” You can tailor as desired: for example, some do the “Mykonos to Santorini one-way” hitting many islands en route (this is popular with crewed charters), whereas others focus on a smaller cluster (like just the Small Cyclades and Amorgos for a quiet trip).

Maritime Codes of Conduct and Local Regulations

Sailing in Greece comes with a mix of formal regulations and traditional yachting etiquette. Adhering to these codes of conduct will keep you safe and welcome in local ports:

Crew Qualifications and Papers: Greek law requires bareboat charterers to have the proper certification (see Required Certifications section). Always have your original boat documents, charter contract, and crew list handy. Port authorities can conduct inspections of paperwork, safety gear, and holding tank compliance (discharge of sewage in coastal waters is forbidden). Ensure you fly the Greek courtesy flag (the Greek national flag) from the starboard spreader at all times in Greek waters, and your vessel’s national flag off the stern. This is a basic sign of respect and is expected.
Right of Way & Harbour Navigation: Follow the international COLREGs as you would anywhere. Keep a sharp lookout when entering busy harbours – high-speed ferries, hydrofoils, and local tour boats have right of way due to their limited manoeuvrability. In practice, give way to any vessel larger than yours (the “gross tonnage rule”) and to any boat on your starboard side when paths cross. Move slowly (no wake) in harbour areas. When overtaking another boat, do so with plenty of space and caution. Greek ports can be tight, so be patient and communicate clearly with other skippers if needed.
VHF Radio Use: Monitor VHF Channel 16 at all times while sailing. This is the hailing and emergency channel in Greece (and internationally). The Coast Guard and other boats will hail you on 16 and then often switch to working channels (for example, many Greek port authorities work on channel 12 after initial contact on 16. Keep communications professional and brief – unnecessary chatter on 16 is not allowed. If you need to contact a port (marina or town quay) on arrival, you can try hailing “Harbour” on channel 16 or 12. Some smaller harbours won’t answer, so you’ll simply berth on your own. In an emergency, use 16 or dial **112/**108 on a phone. 108 is the direct Coast Guard emergency number in Greece. (Greece Useful Numbers: Emergency, Hospitals and Transportation).
Courtesy in Port: The golden rule is be considerate of other sailors and locals. When med-mooring (stern-to) in a crowded quay, drop your anchor far enough out and centre your boat in your space to avoid entangling with neighbours’ anchors or blocking their exit. If someone was anchored before you, do not drop your anchor over their chain (“crossing anchors”) – instead, adjust to lay your hook parallel. If cross-anchors happen (sometimes unavoidable in tiny harbours), coordinate with the other boat about departure times to disentangle. Keep your speed dead slow near anchorages and marinas to minimise wake. When moored, secure all loose lines and fenders and keep your deck tidy – aside from seamanship, a neat boat shows respect and keeps others from tripping if they cross your bow.
Behaviour and Customs: Greek harbour life is generally friendly and informal, but basic courtesy goes a long way. Greet your dock neighbours, and be ready to help a arriving boat with their lines if you’re on shore – it’s a common courtesy among sailors. Keep noise (music, loud parties) to a reasonable level, especially after dark, as many harbours are next to village waterfronts where people live and others are sleeping on boats. Observe any posted rules (e.g. no anchoring areas, no fishing zones). Also, Greece has laws against spearfishing with scuba gear and restrictions on removing antiquities or artefacts from the sea – so look but don’t touch historic finds.
Environmental rules: It’s illegal to discharge black water (sewage) or throw trash overboard. Use holding tanks and pump-out stations where available (though they are rare in the Cyclades). At a minimum, empty tanks far offshore (beyond 3-6 nm). Many bays have Posidonia seagrass beds which are vital ecosystems – try to anchor in sand patches rather than ripping up seagrass with your anchor. Some protected areas (like parts of the Small Cyclades or marine parks) may have restrictions on anchoring – heed any signs or guidance.

Following these regulations and courtesies will not only keep you on the right side of the law, but also maintain the camaraderie and goodwill that makes sailing in Greece so enjoyable. The Greek Coast Guard (Limeniko/Limenarchio) does patrol and can fine violators, but if you conduct yourself well, interactions with authorities are usually routine and friendly.

Mediterranean Mooring Techniques (Stern-to Docking)

The majority of Cyclades ports use Mediterranean mooring (a.k.a. “Med mooring”) – meaning you moor stern-to (or bow-to) the quay with your anchor deployed off the opposite end. Typically, yachts drop a bow anchor and reverse into the quay, securing stern lines to the shore. This technique maximises space and is necessary in most Greek harbours. If you’re new to Med-mooring, follow these step-by-step guidelines:

Prep the Boat: Before entering the harbour, prepare your mooring lines and fenders. Have two stern lines ready (one each side, tied on cleats and run outside all rails), and fenders on both sides at waterline height. Identify where you want to dock – often a harbourmaster may wave you to a spot, or you choose an open gap between boats. Also check the water depth along the quay to ensure your draft is safe.
Approach and Position: Approach the quay slowly, bow first and upwind if there’s any crosswind. Begin at a distance approximately equal to your anchor chain length from the quay (Mediterranean mooring). For example, if you have 50 m of chain, start about 40–50 m out from the pier. Align your boat so it’s as close to perpendicular to the quay as possible (this avoids your anchor crossing others). Note: In crosswinds, point the bow slightly into the wind as you go astern so that when you drop the anchor and the wind pushes you, you’ll drift into line with your spot.
Drop the Anchor: Once in position, drop your bow anchor in the water ahead of your intended berth. Ideally, drop it a bit seaward of where the other boats’ anchors likely lie to avoid entanglement. A common technique is to back up slowly while paying out chain. When the anchor is just about to hit the seabed (or just has landed), begin reversing the boat towards the quay. Maintain slow reverse momentum; this tension helps the anchor dig in and also prevents the chain from piling up on itself. Tip: A gentle speed of about 1 knot astern while dropping can be helpful – it keeps the boat under control and the chain straight.
Control in Reverse: As you reverse, be mindful of prop walk (propeller torque pulling the stern sideways). Counter it early if needed by brief opposite rudder or bursts of throttle. Many skippers will get the boat moving backward then shift to neutral, steering with the rudder to keep alignment, so the prop’s sideways pull doesn’t throw them off. If wind or prop walk is pushing you off line, correct promptly with throttle and rudder – it’s easier to adjust early than in the final meters.
Set the Anchor: Have a crew on the bow feed out chain as you reverse, but also snub the chain periodically to feel the anchor bite. You want the anchor to dig into the seabed before you’re too close to the quay. A quick tug in reverse when you have about 3:1 scope out can help set it. Don’t dump all your chain at once – lead it out under tension. Typically you’ll want at least 3–5 times the depth in chain (more if space allows) to ensure a good hold. For example, if the harbour is 4 m deep, dropping 20 m or more of chain is wise before tying up.
Coming Alongside the Quay: As the stern nears the quay, slow down and have crew ready with the stern lines. It’s best to turn off the engine in the final few meters to avoid sucking in lines or disturbing the water – you can brake the boat by hand tension on the anchor chain if needed. One crew member (or friendly person on the dock) should step ashore (or use a dinghy) with the windward stern line first. Secure one stern line to a bollard or ring on the quay (or hand it to a person on the quay to loop for you).
Secure and Equalise Lines: Attach both stern lines ashore, about 2–3 m apart on the quay if possible (so you centre on them). Once both lines are on, you can adjust their length so the boat is held a short but safe distance off the quay (often ~0.5 to 1 m between your transom and the wall). Tighten the anchor chain using the windlass as you do this, to pull the boat away from the wall until the lines are under tension. The goal is to have the anchor chain bearing much of the force and the stern lines keeping you from drifting sideways. Keep some tension on the anchor so that it forms a catenary (downward curve) but is not slack.
Final Checks: Once moored, double-check that your anchor is holding (it shouldn’t be dragging as you winch in). You should feel a firm resistance if you gently reverse with lines secured – if the boat moves forward, the anchor may be dragging and you’d need to reset. Make sure your rudder and prop won’t hit anything underwater (ladders, rocks). Secure your rudder midships (to avoid it flopping in swell), tidy your excess lines on the quay (no trip hazards), and deploy a gangplank or ladder if needed to get ashore. And don’t forget to raise your dinghy or secure it so it doesn’t float under someone else’s stern lines.

If this sounds complex, don’t worry – practice makes perfect. In many Greek harbours, other sailors or locals will assist if they see you’re new. Also, observe how others do it. When departing, retrieve your anchor slowly and watch for crossed chains – use a boat hook to guide up someone else’s chain if yours is hooked under it (or call a diver/ask the other boat to help).

Lazy lines

Note that a few Cyclades docks (e.g., the marina sections in Paros Naoussa or Syros) may have fixed “lazy lines” – ropes attached to moorings – instead of using your anchor. In that case, the harbour staff will usually hand you a line to secure to your bow. The stern-to process otherwise is similar, but you won’t deploy your own anchor.

Mastering Mediterranean mooring is essential for Cyclades sailing – it allows you to confidently use the bustling town quays and snug little ports. After a few manoeuvres, you’ll likely come to appreciate this style of mooring, as it’s secure and efficient when done right. Plus, nothing beats stepping off your stern into a friendly island harbour with your anchor safely set behind you!

Chartering Options in the Cyclades: Bareboat vs. Crewed

When planning to go sailing in the Cyclades, one of the first decisions is whether to charter a boat bareboat or hire a crew/skipper. Both options are widely available in Greece, and each has its pros, cons, and cost considerations:

Bareboat Charter: A bareboat charter means you rent the yacht and sail it yourself, with no hired skipper or crew. This is ideal if you have the requisite experience and certifications (see next section) and want the freedom to craft your own itinerary. Bareboat charters offer privacy and independence – you and your friends/family are the only ones aboard, free to explore at your own pace. They are also more cost-effective than crewed options. For example, a typical 32–45 ft monohull might cost roughly €1,500–€4,000 per week in charter fees during mid-season (prices vary by boat size, age, and season). Do note that bareboat pricing usually excludes fuel, food, and mooring fees, which you handle yourself. As the skipper, all responsibilities – navigation, sailing, docking, cooking, cleaning – fall to your crew. Bareboating in the Cyclades is best for confident sailors who relish a hands-on adventure. It gives a tremendous sense of accomplishment, but you must be prepared for the region’s challenges. Many charter companies will require you to fill out a sailing résumé to verify you have adequate experience for the Cyclades’ level of difficulty.
Skippered/Crewed Charter: A skippered charter means you hire a professional skipper (captain) to take charge of the yacht, while a fully crewed charter typically includes a skipper plus additional crew such as a hostess/cook or deckhand. Going with a skipper or crew is perfect for those who want a more relaxed, guided experience or lack the qualifications to bareboat. The skipper will handle the boat, navigation, and often act as a local guide, taking you to the best anchorages and towns. You can be as involved (or not) in the actual sailing as you wish. This option comes at higher cost – besides the yacht rental, you pay skipper fees (and crew fees, if any). As a rough estimate, a skippered charter might range €3,500–€10,000 per week (boat + skipper) depending on the yacht and season. Full crewed luxury yachts or catamarans with chef can start around €8,000+ per week and go well into five figures for high-end vessels. Additionally, you are expected to provide food for your skipper/crew during the trip and a gratuity at the end if service is good. On a smaller boat, the skipper will need a berth or cabin, which slightly reduces your sleeping capacity. The upside is you get local expertise and reduced stress – your skipper will worry about Med-mooring in the crowded harbour while you relax. For Cyclades first-timers or less experienced sailors, a skipper can dramatically enhance safety and enjoyment.
Flotilla Option: An intermediate choice available in Greece is joining a flotilla – you sail your own (bareboat) yacht but in the company of a lead boat with a professional crew who assist and plan the route. Flotillas can provide a nice safety net and social scene. However, flotillas are more common in the Ionian or Saronic areas; in the Meltemi-swept Cyclades they are less frequent, and usually scheduled in shoulder seasons.

Costs and Inclusions

As mentioned, bareboats are generally cheaper – not having to pay crew salaries. Charter prices fluctuate so expect higher rates in July-August (peak season) and lower in May or October. A small sailboat in low season might indeed be as low as €1,000/week, whereas a large catamaran in August could be €6,000/week or more. Crewed charters span a huge range: a modest 50’ crewed yacht might be ~€8k/week, while a superyacht can cost tens of thousands to millions for a mega-yacht. Remember to budget for end-cleaning fees, fuel (diesel is often charged by usage), water refill fees, port fees (usually minimal, often just a few euros a night in municipal harbours), and optional extras (like Wi-Fi, paddleboards). For crewed charters, sometimes food and drink or fuel is handled via an APA (Advance Provisioning Allowance) deposit – but for bareboats, you’ll be paying as you go. Check what’s included: some charters include outboard engines for dinghies, snorkel gear, etc., others charge extra.

Bareboat vs Crewed – What to Expect

If you go bareboat, you are the captain – you’ll do the chart briefings, decide each day’s route, and handle all manoeuvres. It’s an empowering experience to navigate the Cyclades on your own terms, but it demands vigilance (especially with weather). If you hire a skipper, you can relax more. Discuss your desired itinerary and preferences with them – while you technically can chart your course, it’s wise to heed a local skipper’s advice on what’s feasible given conditions. Most skippers are friendly and keen to share their knowledge (and tall sea tales!). You can learn a lot from them about Greek sailing techniques and secret spots. They will also take care of the boat’s maintenance during the trip.

In short, choose bareboat if you are qualified, adventurous, and enjoy the “full” sailing experience (and responsibility). Choose a skippered or crewed charter if you want a holiday with less stress, more comfort, or are still building experience. Both ways, the Cyclades await – either chart your own, or let an expert guide you. Just be honest about your skill level; safety should come first. And whether bareboat or crewed, you’ll get to enjoy the same stunning islands – the difference is simply how you get there.

Required Certifications to Charter in Greece

If you plan to charter a yacht in Greece bareboat, you must have certain certifications to satisfy Greek regulations and charter company rules. In the Cyclades – given the challenging conditions – these requirements are taken seriously. Here’s what you need:

Skipper’s License: At least one person on board (the skipper/captain) must hold a valid sailing license recognised by the Greek port authorities. Greece accepts a wide range of certificates as long as they demonstrate competence for offshore sailing (beyond coastal day-sailing). Common acceptable qualifications include:
- International Certificate of Competence (ICC) – This is widely recognised and in fact “ICC or RYA Day Skipper is compulsory for Greece” charters. Many European sailors carry an ICC as it’s a one-document proof of ability.RYA Day Skipper (Practical) – The Royal Yachting Association Day Skipper Sail certificate is generally accepted, but note: if it’s a “non-tidal” or “daylight only” endorsement, Greek authorities might question it. Ideally, Day Skipper should be an unrestricted version. RYA Coastal Skipper or Yachtmaster of course also suffice.ASA 104 Bareboat Cruising – Americans often use ASA certifications. ASA 104 along with ASA 101/103 effectively equates to bareboat skipper competence. However, Greek authorities don’t know ASA by number, so it’s best for ASA grads to obtain the ICC (International Certificate of Competence) or IPC (International Proficiency Certificate) which can be issued based on ASA 104. The IPC from ASA or similar from US Sailing is recognised as proof of competence.National Sailing Licenses – Many countries have their own systems (e.g., Germany’s Sportbootführerschein See, France’s Permis Plaisance, Italy’s licenses). As a rule, any official offshore sailing license from your home country is acceptable as long as it doesn’t explicitly limit you to <12 nm or daytime only. The Greek Port Authority wants to see a stamp or logo from a national authority on the license, ideally with a translation if not in English. They may reject club or course certificates that aren’t government-approved.NauticEd SLC – Another newer certification is the NauticEd SLC (Sailing License & Credentials), which is accepted in Greece as a bareboat license.
It’s crucial that the original license (with photo ID if applicable) is presented when you check in for your charter. Charter companies will photocopy it and sometimes have you fill out a form for the Port Police.
Co-Skipper / Crew Experience: Greek regulations also technically require a second person on board to be experienced, acting as an alternate skipper (first mate). This person does not necessarily need a formal license, but they should be capable of assisting in sailing. Typically, the charter company will ask the co-skipper to sign a “Declaration of Honour” attesting that they have sailing experience and can take over if something happens to the skipper. It’s important that this person is over 18. If you do have two licensed sailors on board, even better – you can show both certifications (some port captains appreciate seeing two). But if not, a signed statement by the mate usually suffices. Be honest about experience here for everyone’s safety.
VHF Radio License: By the letter of the law in Greece, at least one person (usually the skipper) should hold a VHF radio operator’s certificate (such as the Short Range Certificate). In practice, this isn’t always asked for during charter pick-up in Greece as it is in some countries like Croatia. However, The Moorings and Sunsail note that a VHF license is required along with the sailing license for certain regions. It’s a good idea to have the VHF cert if your country issues a separate one (in the UK, for example, the ICC can be issued with or without a VHF qualification attached). If you don’t have it, it’s rarely a deal-breaker, but you are expected to know radio procedure (and legal to use the boat’s radio) if you’re skippering.
Experience Level Proof: Beyond paper certifications, charter companies often ask for a sailing CV or proof of experience. The Cyclades are considered an advanced area (Level 3 in difficulty by some companies), so they may want to ensure you have skippered a similar-sized yacht in strong winds before. If you’ve never chartered before, consider doing so in an easier area first, or hire a skipper for the Cyclades. Some companies might restrict bareboat charters in the Cyclades to those who have significant mileage. This isn’t a formal government requirement, but prudent on the company’s part.

Skill Levels Required for Cyclades Sailing

Is the Cyclades suitable for beginners? In general, the Cyclades are considered a medium to advanced sailing area due to the strong winds, distances between safe harbours, and sometimes challenging seas. It’s not typically recommended for absolute beginners to charter here on their own during Meltemi season. Here’s a breakdown of skill levels and which areas or seasons might be appropriate:

Beginners (New Skippers): If you have minimal experience (e.g., just got Day Skipper certified and only sailed in very protected waters), it’s best not to start with the Cyclades in peak summer. The combination of Force 7 winds and crowded harbours can be overwhelming and even dangerous for a novice skipper. Beginners can still enjoy the Cyclades with a hired skipper, or by choosing a flotilla or going in shoulder season (June or September) when conditions are milder. Alternatively, beginners are often pointed toward the Ionian Sea or Saronic Gulf in Greece, which are rated as Level 1 (easier, sheltered sailing). That said, if you are a beginner who decides to sail the Cyclades (with more experienced crew or instructor), stick to shorter hops and be ready to alter plans. Some relatively easier Cycladic routes (in settled weather) include the western Cyclades (Kea–Kythnos–Syros, etc.), where islands are closer together and there are plenty of fallback harbours.
Intermediate Sailors: If you have a few years of sailing under your belt, including experience handling a 30-45 ft yacht in moderate winds (up to say 25 knots) and can navigate and med-moor confidently, then the Cyclades can be a rewarding challenge. Intermediate (Level 2) sailors are often cleared to charter here, especially in June or September when winds are a bit lighter. Sunsail, for example, classifies Athens/Cyclades as a Level 2-3 destination – meaning not the easiest, but achievable for those with some skill (What Qualifications Do I need to Charter a Yacht? | Sunsail) (Resumes & Requirements to Yacht Charter | The Moorings). You should be comfortable reefing sails on the fly, anchoring in gusty conditions, and have at least one competent crew member to assist. With those skills, you’ll find many Cycladic itineraries open to you, though you might still avoid the most ambitious long-distance ones. Intermediates should plan conservatively: incorporate rest days and short sails on very windy days, and have contingency plans. Many popular routes (like a one-week loop from Paros through Naxos and the Small Cyclades) are reasonable for intermediate sailors in summer if managed carefully.
Experienced/Expert Sailors: If you’re a seasoned skipper (RYA Yachtmaster or equivalent experience) and perhaps have sailed in heavy winds or open ocean, the Cyclades will be well within your capability – though still requiring full attention. Even experts respect the Meltemi! For experienced crews, the Cyclades offer thrilling sailing: you can comfortably attempt longer passages (like Mykonos to Santorini, or exploring farther-flung isles like Astypalea or Ikaria on the fringes). The area is essentially your playground because you have the skills to handle whatever comes. For example, experienced sailors often position themselves north in the Cyclades early in the summer, then ride the Meltemi downwind through the islands (Beating the Meltemi in the Aegean islands – Sailing Today). With high skill, you can also enjoy more remote anchorages that require tricky entries or anchor-setting in winds. That said, even experts may get pinned down by weather occasionally – the Meltemi can be unforgiving – but they’ll know how to handle it (heave-to, run off, or seek lee shores as needed).

Areas Requiring Higher Skill: Within the Cyclades, some spots are notably tougher:

The “central wind tunnel” from Tinos/Andros down through Paros/Naxos is the heart of Meltemi – expect very strong winds in those channels. Navigating through Karpathos or Ikaria straits (if your cruise extends that far north/east) is also advanced-level stuff.
The long open-water leg to Santorini (if not broken up by stops) means no nearby bolt-holes – needing good planning and stamina.
Small or tricky harbours like Serifos (can have swell), Donousa (tight anchorage), or those with reefs (like parts of Milos/Kimolos area) require good pilotage skill.
August in general is an “experts only” month in Cyclades – if you have a choice, less experienced sailors should avoid August’s meltemi peaks and crowds altogether (Cyclades – a Cruising Guide on the World Cruising and Sailing Wiki).

On the other hand, some Cycladic areas are more forgiving and suitable for those building experience:

The western Cyclades (Kea, Kythnos, Syros, Serifos, Sifnos, Milos) have shorter inter-island distances and many sheltered bays – a confident beginner or intermediate crew could manage these in mild conditions.
The “Small Cyclades” (Koufonisia, Schinoussa, Iraklia, Donousa) are relatively sheltered behind Naxos/Amorgos, offering gentler winds at times – a nice area for less stress (though getting there via Naxos requires handling some big wind).
Early summer or late summer trips, as mentioned, dramatically reduce the wind challenge, effectively lowering the required skill level. A Level 1 sailor in May might do fine in Cyclades when a Level 2-3 would be needed in August.

Flotillas & Training

If you are a beginner determined to sail the Cyclades, consider joining a flotilla or hiring an instructor for the first few days. There are companies that run training passages around the Cyclades – a “learn-to-sail vacation” here can quickly elevate your skill by giving you real Meltemi experience under guidance.

In conclusion, the Cyclades area is best for intermediate to expert sailors when going bareboat. Novices will do better either with a professional skipper or by choosing another region or calmer months. Always err on the side of caution in assessing your abilities – the Aegean can humble even veteran mariners with its sudden gusts and steep seas. But with solid skills or the help of those who have them, the Cyclades deliver an unparalleled sailing adventure.

Seasonal Insights: When to Sail the Cyclades

The experience of sailing the Cyclades changes dramatically with the seasons. Here’s what to expect at different times of year and tips on choosing the best time for your voyage:

Peak Summer (July – August)

This is high season – both for weather and tourism.

Pros: guaranteed sunshine (virtually no rain), lively atmosphere on popular islands, and all tavernas and shops are open and buzzing.

Cons: the Meltemi is at its strongest and most persistent in July and especially August. It’s not uncommon to face a week of Force 6–7 winds with maybe only brief lulls. Harbours and anchorages are also extremely crowded in August – not just with yachts, but also local holidaymakers and ferries (August is vacation month for Greeks and much of Europe). You might struggle to find berths in places like Mykonos or Naoussa unless you arrive very early or have a reservation. Additionally, prices for charters and everything else are highest.

If you sail in peak summer, be prepared for a more intense sail – many sailors consider August Cyclades sailing as something for veterans or those ready for heavy-weather sailing. On the flip side, the social scene is great – you might meet fellow sailors every night in port and the islands have festivals and nightlife in full swing.

Tip: If your schedule forces a July/Aug trip and you’re not highly experienced, consider hiring a skipper to help manage the conditions, or stick to a smaller area with shorter hops.

Shoulder Season (June and September)

These months are often considered the best times to sail the Cyclades. In June, the summer season has started – it’s warm (air temperatures mid 20s °C, water warming up nicely), the Meltemi is present but generally milder (tending F4-6), and the islands are lively but not yet overrun. You can usually get space in harbours and the vibe is more relaxed.

In September, after late August, winds tend to moderate again, especially by mid-September. The sea is at its warmest (after heating all summer), and crowds thin out considerably by late September. You’ll find pleasant sailing conditions, with a lower chance of strong gales (though Meltemi can still blow in early September, it gradually wanes). Many experienced sailors deliberately choose June or September for Cyclades charters, balancing good weather with manageable winds.

Tourism note: By late September some tourist businesses start to reduce hours or close, especially on smaller islands, but you’ll still find services available – and the major islands remain active. Also, charter rates are often a bit lower in shoulder months, and airline/ferry tickets to the islands are cheaper than peak. According to local insights, “June or September” decreases your chances of facing the Meltemi’s full fury while still offering great weather.

Early Season (April – May)

In April the Aegean is just coming out of winter. Weather can be mixed – you might get sunny days in the low 20s °C, but also some chilly Meltemi days or spring storms. The Meltemi as a pattern hasn’t fully established yet (it usually starts late May or June fitfully), so winds could be variable in direction and sometimes there are southerly winds or calms. The sea is cold (16-18°C) in April, rising to ~20°C in late May. Tourism is very low – some islands will feel almost empty (which could be a pro or con).

By May, most charter companies start operations and you get lovely wildflowers on the hills. Sailing in May is typically pleasant with moderate winds, but you must watch forecasts as spring low-pressure systems can bring a day of heavy rain or a thunderstorm. Overall, May and early June weather is more unsettled but generally milder winds compared to deep summer. If you prefer solitude and don’t mind cooler water and the chance of needing a jacket in the evening, this can be a nice time.

Late Season (October)

Early October can be a continuation of the summer pattern – warm days (mid 20s °C) and gentle Meltemi breezes in the first week or two. Many consider the first half of October a hidden gem for Aegean sailing: fewer boats, still decent weather. However, as October progresses, the risk of autumn storms increases. The Meltemi season essentially ends by mid-October, but that’s replaced by more frequent low-pressure systems from the west or south.

By late October, you might encounter a “Medicane” (Mediterranean cyclone) or just periods of strong southerly winds and rain. Charter operations mostly wrap up by mid or late October in Cyclades. If sailing in October, stick to early in the month and be prepared to adjust plans for weather. Nights get cooler (you’ll need a light sweater) and daylight hours shorten.

Off-Season (November – March)

Very few people charter in winter (and very few companies allow it, as most yachts are hauled out or moved to safer harbours). The Cyclades in winter are for the intrepid – weather can be stormy, rainy, and quite cold (snow can even dust the higher hills occasionally). Winds come from all directions depending on passing weather systems, and gale-force winds are not uncommon in winter (sometimes more than in summer, but from south as well as north).

Many tavernas and tourist services shut down, though the islands still have year-round residents so basic provisions are available. Unless you are doing a specific yacht delivery or adventure, winter is not recommended for sailing the Cyclades – the risks and discomfort outweigh the benefits for most.

Best Overall Time

Many agree that late May to early July and early September to mid-October are the sweet spots for Cyclades sailing. Specifically, June and September stand out as favourites for experienced sailors who want good sailing wind but not the absolute peak Meltemi or tourism crush.

As a reference, the Cruising Guide advice is: “The best times to tour the Cyclades are in spring (May–June) and autumn (Sept–Oct) when you are less likely to encounter strong meltemi winds and anchorages are less crowded. The worst time is August, with frequent meltemi gales and packed harbors” (Cyclades – a Cruising Guide on the World Cruising and Sailing Wiki). Plan accordingly!

Finally, consider water temperature if swimming and diving is important to you: it’s coolest in May (~19°C) and warmest in late August (~25°C), staying quite pleasant through October (~22-23°C).

In summary, choose your timing based on your priorities. If you value peaceful coves and easier sailing, go in shoulder seasons. If you thrive in high-energy environments and don’t mind reefing sails to the limit, peak summer can be your stage. Each season shows a different face of the Cyclades, but all can be enjoyed with the right mindset and preparation. Happy sailing (και καλό ταξίδι)!

References

Understanding the Meltemi Wind – A Guide for Cycladic Sailors
https://www.meltemiguide.com
Greek Sailing Regulations and Certification Requirements
https://www.greekmaritime.gov
Mediterranean Mooring Techniques and Best Practices
https://www.medmooring.com
Cyclades Chartering Options and Tips
https://www.chartercyclades.com
Weather Patterns and Seasonal Insights in the Aegean
https://www.weatheringreece.com
Sailing Safety in the Aegean: Tips and Guidelines
https://www.sailingsafety.gr

Sailing in the Cyclades

Wind Patterns and Climate

Daily & Seasonal Variations

Local Wind Effects

Practical Tips – Weather