The Cyclades Islands
The Cyclades are one of the largest and most iconic island groups in Greece, located southeast of Athens. Among them are some of the country’s most famous destinations—Mykonos, Santorini, Paros, Naxos, and more—renowned for their whitewashed houses, blue-domed churches, and crystal-clear turquoise beaches that many associate with the essence of classic Greece.
This entire region is characterized by its distinctive architecture, breathtaking coastlines, charming villages, and a rich abundance of ancient ruins.
The name “Cyclades” comes from the word “cycle,” referring to the way the islands encircle the sacred island of Delos—mythologically known as the birthplace of Apollo. Delos is a small island southwest of Mykonos and is officially part of the Mykonos municipality.
In terms of vegetation, the region is quite arid—similar to other well-known parts of central Greece such as the Saronic Gulf and the Dodecanese Islands. This dry landscape creates a dramatic contrast, with rugged mountains and rocky cliffs plunging into the turquoise waters that define the Greek seascape.
So Why Is This Stunning Region Less Commonly Recommended as a Sailing Destination?
Despite its breathtaking beauty, the Cyclades can be particularly challenging for less experienced crews due to several key factors:
The primary reason is the Meltemi wind. During the summer months, the Meltemi blows with significant force across this region, making sailing particularly demanding. This northerly to northwesterly wind typically picks up in the afternoon and can often reach 30–40 knots, especially from July through early September—the peak of the sailing season. While these winds are part of what gives the Cyclades their dramatic allure, they can also turn an otherwise pleasant voyage into a difficult or even dangerous experience.
The shoulder seasons—April to mid-June and mid-September to October—tend to be more manageable, but even then, close monitoring of weather forecasts is essential, and daily consultation with local sailors is strongly recommended.
In addition to the wind, the islands are spread out across a large area. This means that within a standard one-week charter, starting and ending at the same base marina (typically Lavrio), it’s only feasible to reach a limited number of islands. Interestingly, many of the most famous Cycladic islands are located beyond a comfortable range for a week-long itinerary, particularly for leisure crews or families.
What complicates this further is the return leg. Most routes head southward at the start, with the Meltemi at your back. However, returning north often requires beating into the wind—an uncomfortable and potentially hazardous leg, especially when weather forecasts aren’t reliable more than a few days out.
The region is also notably more exposed than many other sailing areas in Greece, lacking the natural protection offered by enclosed gulfs or closely spaced island chains. This means that sea conditions can deteriorate quickly and unexpectedly, particularly in summer, creating rough passages and challenging anchorages.
Adding to the challenge, most marinas and ports in the Cyclades are small and can be overcrowded during the high season. Combined with strong winds, maneuvering and mooring in such tight spaces can be especially difficult for less experienced skippers.
That said, it’s important to stress: the Cyclades are absolutely sail-worthy—but best suited for confident, experienced crews who are comfortable handling strong winds, long passages, and the Mediterranean mooring style, even under pressure.
For those seeking adventure, the Cyclades offer a truly rewarding experience—particularly on longer itineraries of two weeks or more, where there’s more flexibility to explore distant islands, wait out weather windows on land, and enjoy the region without the time constraints of a standard charter.
Charter Bases in the Cyclades Region
The most convenient departure point for sailing in the Cyclades is Lavrion Marina, located just south of Athens—about a 30-minute drive from the international airport. This makes access easy with a single flight and a short transfer, and the marina’s location allows for a very quick sail directly into the island group.
Another option is Alimos Marina in Athens, one of the largest charter bases in Greece. While this base offers a wider selection of yachts, starting your trip from Alimos adds at least a full sailing day each way—both at the beginning and end of your charter—making it harder to truly reach the heart of the Cyclades during a standard one-week itinerary.
A third, less common option involves starting from a small, local charter base on one of the islands within the Cyclades themselves. These are typically operated by one or two companies and, while they offer excellent access to the islands from day one, getting to these bases is logistically more complex and less convenient for most sailors.
Important Note / Safety Reminder
All of our anchorage and bay recommendations are entirely dependent on favorable weather conditions. The Cyclades are known for frequent strong winds, and in such conditions, anchorages that are otherwise beautiful can become uncomfortable at best—and unsafe at worst, with swell and gusts.
The iconic images of crystal-clear turquoise waters in tranquil bays? Those are taken when there’s no wind.
It is essential to monitor weather forecasts closely and to adapt your sailing route accordingly, day by day. Never rely on fixed plans—safety and comfort must always come first.
For your convenience, all highlighted location names on this page are linked directly to their coordinates on the NAVILY map, allowing you to explore, plan, and review real-time local conditions as part of your trip preparation.
Planning the Sailing Route for Your Holiday
There are many factors to consider when planning a sailing itinerary, which is why we’ve chosen not to recommend one fixed route, but rather to present a variety of highlighted points of interest. The best route is the one that’s right for you—and that same route might be completely unsuitable for another crew.
Some sailors enjoy covering long distances, while others prefer shorter hops. Some seek quiet anchorages, others want a lively quay and a good taverna each night. And of course, beyond all these preferences, the most important factor is the daily weather.
We believe that the best way to sail is to make smart, flexible decisions day by day, based on the most recent forecasts—not to stick rigidly to a pre-planned route. That could mean battling rough seas unnecessarily, or sailing in conditions that exceed your comfort or capabilities as a crew.
So instead of giving you a fixed itinerary, we’ve provided a selection of recommended spots in each sailing area. This way, you can build a route that suits your sailing style—and adapt it during the week as needed.
Wishing you enjoyable planning and an amazing sailing adventure!
– Ronen & the SAILING AROUND team
A tiny, narrow island about 3 kilometers long, located very close to Lavrion. Makronisos is nearly uninhabited, aside from a few small churches and archaeological remains—so there are no marinas here.
However, the island offers two beautiful bays that are perfect for a swim stop or even an overnight anchorage for those seeking peace, nature, and quiet solitude.
Recommended Anchorages:
1. O. Vathiavlaki
A small and beautiful bay offering nothing but peace and nature all around.
Ideal for a midday swim stop or an overnight anchorage—weather permitting.
Gerolimionas
Another peaceful bay, ideal for a midday swim stop and short rest in calm surroundings.
2.KEA ISLAND
A relatively large and inhabited island, Kea differs from the more southern Cycladic islands in that it doesn’t feature the typical white-and-blue architecture the region is famous for.
The island has two marinas, both located within the same bay on the northern coast: one is a proper town marina with full facilities, while the other is smaller and more locally run.
Kea is dotted with beautiful bays all along its coastline, making it a great spot for daytime stops or overnight anchorages, depending on conditions.
Marinas:
1.ORMOS LIVADHI MARINA
A functional marina located next to a small town. While it may not be the most picturesque or charming spot, it certainly offers an authentic Greek coastal vibe.
There are a few tavernas and restaurants right by the marina, and limited but pleasant walking areas nearby.
VOURKARI MARINA
Located in the same bay as Ormos Livadhi, Vourkari is a small and charming marina—or more precisely, a single quay set in a beautiful and protected inlet.
There are a few restaurants and beaches nearby, making it a cozy and convenient stop.
If you’re in the mood to explore inland, renting a car or scooter is a great option. Head up into the mountains to discover scenic villages, ancient ruins, breathtaking viewpoints, and don’t miss the famous Stone Lion of Kea near the island’s old capital.
Recommended Bays:
A very large and sheltered bay, except from the north. Tourist-friendly beaches, with restaurants scattered around. Very suitable for a midday stop or an overnight stay, weather permitting.
A very large bay, well protected from the north and west, less so from the south and open to the east. Features organized swimming beaches.
Possibly the most beautiful bay on the island. A large bay with stunning views, surrounded by arid mountains and a large, impressive archaeological site directly above the bay. If you’re sailing to Kea and have to choose just one spot, in our opinion – this is the place (except in strong south winds).
A classic and beautiful Greek island, definitely worth a visit. Two charming marinas, stunning landscapes, picturesque villages, and countless beautiful turquoise bays. If you have time to explore the island, it’s highly recommended to rent a car or scooter and head up into the mountains and villages, and visit some of the amazing beaches scattered along the island.
Marinas:
A small, charming, and well-organized marina. A lovely little village surrounds it, with tavernas and natural hot springs that flow into the sea.
2. MERICHAS MARINA
A small, well-organized city marina with everything you need around it.
Recommended Bays:
A magical bay with a strip of sand between two coves leading to a peninsula. If you’re in the area and looking for a beautiful bay, this is definitely the place! Perfect for a swim stop or an overnight stay at anchor. There’s also a taverna on the beach 🙂 One of the most beautiful spots and one of the best sunsets in Greece 🙂
A large and beautiful bay, relatively quiet and calm compared to more touristy spots. Open to the west.
A bay with a large and beautiful beach. Relatively quiet. Open to the southeast.
A small and magical bay – open to the south. Very, very beautiful. Taverns, a few houses, and a church on the beach. There are places to walk around and explore the surroundings.
A quiet, beautiful bay with stunning views. Along the shore, a few scattered houses, a taverna, and traditional agricultural terraces – incredibly scenic! Recommended for those who love nature and tranquility.
4. SERIFOS ISLAND
A small, quiet, and not very touristy island. Full of beautiful bays ideal for swim stops or overnight stays. There’s one small city marina — the marina itself isn’t particularly attractive, but the surrounding village and the Chora (the old village center) at the top of the hill (requires a vehicle to reach) are very charming.
Marinas:
A small city marina — the marina itself isn’t amazing, but the surrounding area is very, very beautiful. Definitely worth renting a car and exploring the island.
Recommended Bays:
A large and beautiful bay with a very wide beach. Slightly touristy. The bay is well protected from all directions except directly from the south. Two neighboring beaches are also beautiful, so you can choose whichever spot is most comfortable and available.
https://www.navily.com/carte/mouillage/24197
https://www.navily.com/carte/mouillage/17948
A small, quiet, and magical bay. Perfect for those who love nature and tranquility, with nothing on the beach.
A large and beautiful bay, with tavernas on the beach. Note that it is open to the north.
A tiny bay, but one of the most beautiful spots! Possibly the most stunning bay on the island. Perfect for a swim stop or an overnight stay, weather permitting and if there’s space. The bay can accommodate two, maybe three yachts for a comfortable overnight anchorage. An amazing spot with a small sandy strip leading to a peninsula with a hill and a monastery on top. A magical place.
5. SIFNOS ISLAND
A small island, but without a doubt one of the most beautiful. Mountains, landscapes, ancient ruins, bays, and entire villages in white and blue — everything here is simply stunning. The island has two very small marinas and several bays, each more beautiful than the last 🙂
It’s definitely an island worth stopping at for a day — rent a car and explore the island.
Marinas:
A small and charming city marina. The marina is set within a beautiful bay surrounded by high mountains and stunning views. White houses are scattered across the surrounding slopes. A classic Cycladic-style marina. Keep in mind there are only 8 berths available on the dock, but there is plenty of space to drop anchor outside the marina and enjoy the view and the village.
https://www.navily.com/carte/mouillage/15992
The only downside of the marina is the frequent ferry traffic. Keep that in mind when choosing your anchoring spot.
Another small and charming marina. Slightly larger, with around 15 berths, and perhaps a bit less picturesque than Kamares, but still features a beautiful bay, village, and stunning surrounding views. Here too, there is a wide area along the shore outside the marina where you can drop anchor.
Recommended Bays:
A small, magical, and authentic bay — definitely one of the most beautiful and unique. An amazing spot for an overnight stay at anchor, with a fishing village and tavernas around.
Recommended Bays:
A small, magical, and authentic bay — definitely one of the most beautiful and unique. An amazing spot for an overnight stay at anchor, with a fishing village and tavernas around.
Another must-visit spot if you’re in the area! You can stop for lunch, spend the night if the weather allows, or even reach it by car from one of the marinas — or simply sail past to admire it during your trip without stopping. A stunning bay, a beautiful village, and a monastery perched on a dramatic cliff. Definitely one of the most beautiful places.
Another stunning bay along the southern chain. A well-maintained and beautiful beach. It can get crowded during the season.
6. PAROS ISLAND
One of the most well-known and touristic islands in the area. The island is very organized and developed, and full of tourists — partly because it has an airport with direct flights throughout the summer from several destinations, including Israel. So, if you enjoy more structured and lively places that are still incredibly beautiful, this is the spot for you. But if you prefer the natural, peaceful side of Greece, you might want to consider nearby Antiparos — a quiet and laid-back destination off the beaten tourist path.
Paros is definitely a great and convenient island to spend a day or more on, with a rental car and time to explore this charming island.
There are two relatively large and organized marinas on the island (by local standards), but it can still be very difficult to find a berth during the season — keep that in mind. One is a large and organized marina in Parikia (the main town of Paros), and the other is a slightly smaller marina in the lovely village of Naoussa, which is a tourist attraction in itself and a must-see during your visit to Paros.
Marinas:
A large (relatively) and well-organized city marina, right next to the charming town. A great base for renting a car or scooter and exploring the island. Outside the marina, there’s a beautiful and spacious area along the shoreline within the bay for anchoring — ideal for those who prefer not to enter the marina itself or in case there’s no space, but still want to enjoy Paros.
Naoussa is a charming Greek village that’s definitely worth a visit and a stroll. So if you’re in the mood for a night in a marina but not in a big city, this is the place. Just keep in mind that the marina is small, and during the high season, there’s a good chance you’ll end up anchoring outside the marina.
Recommended Bays:
A sheltered area with a stunning coastline! Just keep in mind that it’s quite touristy during the season, and the beaches are organized and busy. If you stay overnight, the village of Naoussa is also within dinghy distance.
A wide and spacious bay, open to the west, with a large and beautiful sandy beach.
7. ANTIPAROS ISLAND
The neighboring island right next to Paros is the quieter, less touristy alternative to Paros. However, there is no marina that can accommodate sailboats, so it’s only suitable for a midday stop or an overnight stay at anchor — ideal for those who enjoy and seek more nature and tranquility.
For those who still prefer tavernas and anchoring near a village, this is the option in Antiparos. Drop anchor just outside the town’s small fishing harbor.
A beautiful rocky beach, perfect for a swim stop — of course, when the weather is calm 🙂
A perfect spot for a swim stop, weather permitting. A small cave and a natural rock arch you can swim through. A very beautiful place.
A very tiny bay, but absolutely stunning! Perfect for anyone seeking wild nature, peace, and tranquility. Space for only 2–3 yachts at most. If it’s full, you can continue to the neighboring bay, which is also amazing.
https://www.navily.com/carte/mouillage/24092
8. NAXOS ISLAND
It is the largest island in the group, and it also has an airport. It is very touristic and well-developed. That said, it doesn’t take away from the island’s stunning beauty — mountains, villages, bays, tavernas, and everything we love about Greece. The island is known for its white sandy beaches and popular kite-surfing spots. However, these areas are usually packed with tourists and less suitable for yachts.
There is one marina on the island — a beautiful, well-organized city marina located next to the stunning town of Naxos. Despite the size of the island and the town, the marina has only 25 berths, so don’t count on finding a spot 🙂
There is also a tiny harbor in the village of Kalantos on the southern part of the island, but it has just a few berths available for yachts.
If you’re looking for quieter and more pastoral spots, you might want to skip Naxos. But if you enjoy lively towns and organized beaches along with breathtaking views — this is absolutely the place for you.
We managed to choose only one bay from the entire island, as most beaches are very crowded, with music and water sports, so we avoided recommending more.
Marinas:
A city marina, but in one of the most beautiful towns in Greece. If you’re looking for a night in an organized, urban setting — this is the most scenic place to do it. A stunning town with whitewashed houses, an old historic center, and plenty to explore around.
If you arrive and the marina is full but still want to visit the town, there’s a sheltered area just outside the marina where you can drop anchor.
A tiny harbor with a single dock for just a few yachts, located in the heart of a beautiful bay. If there’s no space at the dock, it’s absolutely possible — and recommended — to drop anchor along the charming shoreline.
https://www.navily.com/carte/mouillage/22624
Recommended bays:
A magical, well-protected bay. There’s a tavern, there are antiquities – definitely worth a visit for a lunch stop and absolutely also for the night if the weather permits.
9. MYKONOS ISLAND
Perhaps the most famous and well-known island in the region. It also has an airport with direct flights and active Israeli and international tourism. The island is very famous for luxury tourism, white houses (found on most islands in the region), parties, clubs and beaches. All of these might actually be reasons NOT to come here if you’re looking for the quiet and pastoral Greece we usually encounter on sailing trips – you probably won’t be able to find a single bay here without music on the beach throughout the summer, at least we couldn’t… But if an urban experience and vibrant nightlife combined with Greek scenery suits you, this is the place for you. Keep in mind that in accordance with its character, the island is significantly more expensive than most of the region, which is already relatively expensive compared to other areas in Greece, and the atmosphere is very different from what we know from most Greek islands.
The island has one large marina (relatively speaking for the region) but with quite harsh reviews on NAVILY, very few services, and despite this, very high demand and difficulty finding available space during the season. And keep in mind that in addition to the many ferries, large cruise ships also arrive here frequently and regularly throughout the summer.
Marinas:
The only marina on the island. 50 spots, relatively large for the region. Surprisingly without any services at all except for mooring space and the possibility to refuel. No water and electricity, no showers. The marina is quite notorious in relation to yachtsmen – keep this in mind. Additionally, note that you cannot arrive without booking a spot in advance!
Recommended bays:
A beautiful bay with a large sandy beach. Part of it is organized for tourists with sun loungers and a beach bar.
10. TINOS ISLAND
A relatively large island that is, for now at least, completely off the known tourist track in the region. So if you’re looking for some quiet and scenery at several levels less chaotic than the more famous islands, this is a great visit. The island has two small marinas. One in Tinos town itself, a municipal marina within the port, and another marina or more accurately just one municipal dock with a few mooring spots 🙂 and an extensive area around it to drop anchor, with a quiet and charming village nearby.
Definitely recommended to rent a car here and tour around the island.
Marinas:
A municipal marina that is part of a larger municipal port. There aren’t many mooring spots and it’s not the most pastoral and quiet place. The town is definitely charming and it’s an excellent place to stock up and also to rent a car and tour the island, which has many charming corners and beautiful beaches.
The quieter and more beautiful alternative to the marina on the island. Only it’s not really a marina but rather one municipal dock with few spots and plenty of room to drop anchor along the adjacent coastline. A charming and completely quiet Greek village outside the tourist circuit. Very suitable for those looking for quiet and a slightly more authentic and less touristy Greece. An excellent point also for going on walking trips or by vehicle around the magical island.
Recommended bays:
A protected bay open only to the north. Large and beautiful beach, part of it with nothing, part of it organized for tourists. Stunning scenery. Worth a stop and even an overnight stay if the weather permits, of course.
Another excellent point for a swimming stop in southern winds (open to the north) – a charming bay.
A large and beautiful bay with a sandy beach along its entire length. Protected to the north. Relatively quiet and without many tourists. An excellent swimming spot when the weather is suitable.
11. ANDROS ISLAND
A relatively quiet and charming island that combines a bit of everything. Landscapes, villages, antiquities, bays and much of Greece’s charm. One relevant and charming marina. Some magical bays and plenty of places to explore around the island.
Marinas:
A charming municipal marina, in a lovely village full of tavernas and charming corners. Definitely worth an overnight stop and also an excellent base for island tours. If you’re renting a car to get around the island, don’t miss a visit to Andros town itself, which is located on a kind of promontory above the water and creates a very special view.
Recommended bays:
A beautiful bay with a large sandy beach. There’s a taverna on the beach. Perfect for a swimming stop or overnight stay. Of course when the weather is suitable.
Another wide bay with a huge and beautiful sandy beach. This beach isn’t really developed and is mostly empty. A charming and perfect place for swimming or overnight stay when the weather permits.
A small bay that’s quite open except to the west. But in calm weather it’s a beach stunning in its beauty.
A small and quiet bay with nothing on the beach. Stunning scenery around with a beautiful beach. A perfect place for those seeking nature and quiet. Note that it’s open to the north.
A relatively large bay, with a beautiful and completely undeveloped beach! Tourists still arrive but as of summer ’23 the beach is empty of businesses and umbrellas. Perfect for a swimming stop or overnight stay for those who love quiet and nature, of course only in suitable weather.
Even if you’re just passing through the area without stopping, you must sail by and peek at the bay and the beauty that sits on the cliff/promontory into the sea with one of the most beautiful lighthouses you’ll ever see. Visit, you won’t be disappointed. And if you’re already here and the weather is calm, then the place is definitely suitable for dropping anchor and jumping into the water 🙂
12. SYROS ISLAND
If you want to visit a large, vibrant and bustling port city that’s full of Greek charm and magic – to walk through enchanting alleys, shops, churches, impressive architecture right from the waterfront up to the mountains above, antiquities, museums and more… then this is definitely the place to visit! The island is beautiful and dotted with amazing beaches and bays, but there’s no doubt that this time we especially recommend visiting the large and special city – ERMOUPOLI.
The island has a large central port around which the city of ERMOUPOLI is built, and it contains a relatively large and organized marina. On the other side of the island, there’s another marina located in the village of FINIKAS.
Marinas:
So as we said, if it suits you to give up pastoral villages for one day and go for a visit to the big city – but a beautiful city full of Greek charm and magic with tons and tons to see and do in the city and surrounding area – this is the place! The marina is indeed located alongside a large commercial port and you need to take that into account, but the city is absolutely worth the visit and in our opinion is one of the must-visit points in the area.
A small and beautiful fishing harbor with several spots for yachts on the breakwater (facing south, the bay is protected from other directions) both inside and outside. A cute village, tavernas, bakery, relaxed Greek atmosphere 🙂 If there’s no space in the harbor you can drop anchor along the coast outside, as long as there’s no southern wind the bay is relatively protected…
Recommended Bays:
A tiny and magical bay. Just wild nature and tranquility. There’s room for only a few individual yachts!
Another magical and tranquil bay. Stunning in its beauty and again just wild nature and peace. The bay is divided into three sections – you can anchor in all three. Highly recommended to take a few hours to wander and hike on the peaks around! The view is amazing! One of the most beautiful places.
