Sail the Greek Dodecanese Route

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.

590€ 490€* PP
*early bird price until 31.03.2019

📆 7 nights, departures:
19th October 2019
✈️ Kos (KGS) or Rhodes (RHO) Airport
🌊 Southeastern Aegean Sea
🔵 Easy Route

Yachts Confirmed:
1) Oceanis 45, 2015 Built, 4 cabins, 2 heads, 8 crew + skipper
Total Yachts Expected: 3

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!

What people say about Naleia
Naleia is awesome for everyone who enjoys traveling and a little adventure. I've been on the first trip to Croatia and it is great to see how far Naleia has come since. There is a variety of routes, I like the idea of social deposit scheme and it always attracts nice lovely people to share the trip with. Skippers are top notch and you will be able to balance learning how to sail with a few relaxing days at the sea with all it's joys. I'm now on the way to Thailand trip and can't wait to start
09:42 10 Feb 19
I usually fly solo when traveling, and it never occurred to me to sign up for a package tour. But I took a gamble here and Naleia exceeded my expectations. They have somehow figured out how to get adults to buy into a sincere spirit of group adventure and camaraderie without it ever feeling forced. And obviously, the locations are beautiful, the other people are engaging, the sailing is fun (you'll grow in confidence throughout the week), and it's clear that the Dominick and his team really care about the experience they are creating. You can easily do this trip alone, with friends, or with your significant other. I'm sure I'll sail with them more
Holly Masek
Holly Masek
14:15 03 Oct 18
Stop thinking about sailing with Naleia... and just book it. You’ll love it! Your fellow crew members are a wonderful bunch – and we had the most laid-back skipper ever to roam the Med. The scenery is amazing and varied: you’ll moor-up in a port one night amongst super-yachts then drop anchor the following night in a nearly-deserted bay. You’ll learn so much if you’ve never sailed before, but it’s all really relaxed. I’m so glad I took the plunge – you will be too. Maybe see you out there one day more
Suzanne Lantos
Suzanne Lantos
14:00 21 Jul 18
Dominik has an amazingly ability to make everyone feel included and have a great time while also teaching new skills. But the best part is that people grow and learn new skills for life and learn things about themselves without even knowing. I’m already booked on another trip and have made new connections with people that I know will be friends for life. Thank you all.
Gary Jenkinson
Gary Jenkinson
22:41 17 Jun 18
Well organised trip, with Dominik competently answering all questions before the trip. Skipper Nico with endless patience to teach the basics of sailing to complete Newbies - I'll be back!
17:38 17 Jun 18
Loved the sailing trip to Azores.Dominik and the crew were amazing!We had a beautiful experience whalewatching and learning the basics of sailing.I'll definitely sail with Naleia again!! 🙂
Giuseppe Enriquez
Giuseppe Enriquez
12:43 14 Jun 18
Having done the 'Same Same' tour in Thailand. It was one of the most amazing experiences we had. The snorkeling was beautifull and we saw so many fishes and coral. The group of people we were with was great and spending time with experienced skippers we learned a lot about sailing. I highly reccomend it. One tip, do bring your seasick pills if you are sensitive to that. You don't want to recover from your seasickness while the rest of us is swiming in bioluminescent glow in the dark plankton and having an amazing time.Cheers, Joao and Margaread more
joao caldeira
joao caldeira
08:54 08 May 18
I had such a great trip with Naleia! Me and my friends sailed in Thailand with them. It was wonderful. Our skippers Marc and Nico are the friendliest, most fun and professional people. Being on a boat for 10 days is a intense experience, exciting and deeply relaxing at the same time!Sailing is such a gentle way of traveling, you have to be in tune with nature. Our skippers managed to avoid most mass tourism by arriving at our destinations for the night just when everyone else was leaving. This meant that we had the most beautiful islands to ourselves. Thailand is such beautiful country and the islands we discovered were absolutely stunning. I especially loved snorkeling in Ko Ha.On top of all the wonderful experiences we learned about sailing. Hoisting the main sail, standing at the helm, doing tacks, ankering etc are all very empowering experiences!I absolutely loved the trip and am planning to go on other trips with Naleia!read more
Teresa Liska
Teresa Liska
01:50 03 Apr 18
Great sailing experience.. well not too much wind in the Seychelles in February but still an awesome trip! And Nico's a 5 star skipper 🙂
Cba Xyz
Cba Xyz
16:34 02 Mar 18
I had the best time in Croatia. If you ever had the thought to try sailing, I can thoroughly recommend Naleia! The organisation is superb, the people are warm and open and you will learn much more than just the sailing itself. Personal highlights include spotting dolphins, feeling us come together as a team, swimming in deep blue waters and enjoying local restaurants in remote locations accessible by the sea.
Steven Lynch
Steven Lynch
13:26 16 Sep 17
I just went to Croatia with Naleia and I can honestly say it was the best vacation I've ever had. It was the perfect mixture of adventure and relaxation. Dominik and Marc were fantastic skippers, and yacht life is the best life! Equally as important is the community that Naleia cultivates, we traveled with a great group of diverse people who were interesting, easygoing, and fun to spend time with. I will definitely be sailing with the Naleia crew again soon.
Elizabeth Moody
Elizabeth Moody
15:28 22 Aug 17
I joined the Croatia Sunset Route with Naleia having never sailed in my life before and finished as a competent crew member of a fun and international team of new friends. I’d thought about joining a party cruise and seeing some beautiful scenery along the way but the connection with nature and the flexibility of being on two small yachts was so much better as we were able to visit tiny local villages and go swimming and snorkelling in bays that would have been inaccessible otherwise.Learning to sail – great! Making new international friends – great! Flexible personalised routes - great! Professional organisation – great!Beautiful Croatian scenery – great!read more
Bryn French
Bryn French
16:43 19 Aug 17
I went on a trip to Croatia having never sailed before and couldn't have had a more positive experience. The skippers were friendly and happy to teach, the boat quickly became a team and a lot of thought was put into the program of the day! Highly recommended for anyone looking for an adventure on the high seas with a great bunch of people.
Christopher Mills
Christopher Mills
18:16 17 Aug 17
I went on a week trip in Greece, and would definitely recommend sailing with Naleia! Great organization, very kind, fun and interesting people, and amazing places. Personally, it was quite a different travel experience, which I welcomed since that was what I was looking for. Also, you don't need previous sailing experience. Learning is really fun! It was great, I'm looking forward to doing it again!
Maria Bertogli
Maria Bertogli
11:33 07 Jul 17