Sail The Greek Dodecanese Islands

Sit back, relax, enjoy, savour.

The perfect balance between
tranquility and charm

The Dodecanese (dódeka nisiá = literally “twelve islands”), the easternmost group of islands just off the coast of Turkey, are known to be the sunniest part in Greece. They’re defined by crystal clear waters, sandy or pebbly beaches, important archaeological finds, imposing Byzantine and medieval monuments waiting to be discovered. We’ll take in the cosmopolitan Mediterranean flair of the historic towns of Rhodes and Kos, and discover the lesser-known, unspoiled destinations on the smaller islands. Every island has their own unique geography, landscape, culture and feel. And maybe we’ll see dolphins while sailing between them, if we’re lucky.

7-day return trip from kos

To see all the Dodecanese, north and south of Kos, you’d need at least 2 weeks. But one week is enough for a taster, and Kos is the easiest starting point from which to experience a bit of both sides: the north and the south, the well-known jewels as well as the more remote secrets. Our tentative itinerary isn’t too intense, averaging about 4-5 hours of sailing a day, and the rest, leisurely time to explore and enjoy the beauty of these unique islands.

We decided to place this route towards the end of the season in order to avoid the bulk of the tourists and charge up some sun while autumn rules the northern hemisphere. The air and sea will still be nice and warm, swimming opportunities will be plenty, and hopefully we’ll have the ports and taverns mostly to ourselves, and be able to experience the region in a more authentic light.

“Dodecanese” Route

⛵ 7 nights sailing,
☸️ professional skipper, 
🏨 bed linen, towels, end cleaning,
🏄 SUP board and dinghy,
🔒 trustful damage deposit,
💎 travel insurance.

💰 cashbox contribution ca. 130 € pp (food, port fees, fuel),
✈️ flights/transfers.

Departure: Kos Island Marina, Kos Town.

Nearest Airport: Kos Island International Airport (KGS)

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*To sail at other dates; to organize a private trip; to get in touch.

Sail from island to island

A different island every day, each with its own unique charm, character, and landscape!

Charming Greek Villages

Experience life’s purest pleasures. The laidback style of these charming little villages, and the delicious smells of fresh bread and fish emanating from their tavernas, will make for lasting memories.

Your home for a week

Experience authentic sailing on a 12-16m yacht. Live on board, become a team with your fellow crew members, learn the ropes, and feel the wind and sea. Enjoy the neverending views from the deck of your floating home.

Dodecanese Sailing Highlights

What you can expect to see and do on this route.

Dodecanese Sailing Itinerary

We are true to the discoverers’ spirit and plan our adventures accordingly to the winds, the weather and your wishes. This means the order as well as some of stopovers may be different than presented below. Leave planning at home! The plan showed below is only an indicative itinerary and your trip may differ. Only the mad ones sail against the wind!



We’ll have a great time walking around car-free pedestrian-friendly Kos, exploring cafes, taverns, restaurants and shops. Sandy beaches, turquoise waters, tree-lined wide roads, parks and vegetation make this a spectacular place to start our holiday. If we have time, we’ll explore beyond the town: for example, Zia is a beautiful, mountainous village – the highest point on Kos – with amazing views of the island. And maybe we’ll set anchor near Kefalos, a lovely resort with beautiful beaches and crystal clear waters which has managed to keep a lot of its whitewashed house and narrow alley charm despite its popularity.



Also known as the “island of the sea sponge harvesters”, after WWII Kalymnos remained the only Greek sponge-harvesting industry supplying both domestic and international markets with sea sponges. An internationally known alternative tourism destination, it’s popular among climbers and boulderers all year long. Póthia, the capital and the port of Kálymnos is spread majestically on two hills, and there are a number of interesting old ruins to visit.



This was one of our skipper Marc’s favourite islands, with a 3 kilometre wide active caldera in the middle. We’ll moor up in the lovely little town of Nisiros and rent scooters or a van in Paloi to go drive around the island and explore its volcanic centre. We’ll finish off our exciting day of adventure on land with some lovely seafood, chocolate cake, and/or ouzo!



Ragged mountainscape, densely forested ranges and hilly vistas, Tilos is an amazing ecological park protected by international treaties. Megálo Chorió, the island’s capital, boasts imposing stone houses, narrow alleys, a very cute small port. The view from the medieval castle at the top of the hill will certainly take your breath away. Alternatively, a walk to Mikro Chorió leads to an impressive abandoned ghost town. Definitely worth exploring.



The capital of Chalki is built amphitheatrically above the crystal clear sea, preserving its noble beauty, its picturesque alleys and its unique architecture. It is known as of the prettiest neoclassical settlements of Greece! We could hike up to see the sunset over the harbour, or just hang out sitting in a café watching old men play chess.



The largest of the Dodecanese, Rhodes lies close to the Turkish coasts. In ancient times, it was famous for one of the Seven Wonders of the World, the Colossus, a giant statue of the god Helios that towered over the harbour. Today, Rhodes is famous for its more tranquil side – lovely beaches, lush landscape and traditional villages. Rhodes Town, on the northernmost part of the island, is divided in the Old and the New City. The Old City is one of the best preserved Medieval sites in Europe. If we have time and the winds are favourable, we can set sail for Lindos, which boasts superb beach coves and it is dominated by an imposing acropolis that overlooks the picturesque bay.


Keep the connection

Day 8 is the day to say goodbye. All the miles sailed, islands visited, skills gained and time shared with others will make you bond and build relationships. Cherish these, keep in touch and remember that the Naleia Sailing family is there. Hope to see you onboard again soon!

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