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Yacht sailing holidays & skippered tours in Dodecanese

Discover hundreds of sailing holidays in the Dodecanese Islands. Book a spot onboard and live a unique experience with a local skipper. Starting at €400 a week.

experiences

4.9

Super!

From Kos to Rhodes: the beautiful south Dodecanese

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€800

Per person

5.0

Super!

The enchantment of the sea: the Dodecanese islands

Greece: Dodecanese

7 days - 7 nights

2 departures available

September

Starting from

€650

Per person

5.0

Super!

Secret Aegean with skipper and kitchen on board from Kos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

September

€1,050

Per person

5.0

Super!

Treat yourself to an unforgettable holiday. Embark with us in Kos

Greece: Dodecanese

7 days - 6 nights

One departure available

August

€1,000

Per person

5.0

Super!

Secret Aegean with skipper and kitchen on board - Rhodes to Kos

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

4.9

Super!

From Rhodes to Kos: the fantastic South Dodecanese

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€880

€836

Per person

5.0

Super!

Secret Aegean with skipper and kitchen on board - Rhodes to Karpathos

Greece: Dodecanese

7 days - 6 nights

One departure available

September - October

€950

Per person

5.0

Super!

Secret Aegean with skipper and kitchen on board - Karpathos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

5.0

Super!

Sailing in the eastern Aegean, between the Dodecanese and the Cyclades!

Greece: Dodecanese

8 days - 8 nights

One departure available

September

€650

Per person

5.0

Super!

Experience the sea at 360 degrees? embark with us in Kos

Greece: Dodecanese

7 days - 6 nights

2 departures available

July - September

Starting from

€850

€750

Per person

5.0

7 islands in VIP formula - only 4 guests on board

Greece: Dodecanese

8 days - 8 nights

One departure available

July

€1,350

Per person

4.6

Cruise in the Dodecanese and off the coast of Turkey on a 17m boat with chef

Greece: Dodecanese

7 days - 7 nights

2 departures available

August

€1,600

Per person

Why book a holiday with Sailsquare?

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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Yacht sailing holidays & skippered tours in Dodecanese

197 reviews

Experience the sea at 360 degrees? embark with us in Kos

07/9/2025

Davide M.

Italy

Undecided about the choice of holiday to face, Gianfranco immediately put me at ease, so much so that it was difficult to get off his "[hidden]" on the last day. Crazy holiday with swimming in spectacular pristine coves not to mention the excellent restaurants he recommended. Gianfranco find me a location where you can dance Boogie boogie for June 2026 . Thanks again and we will see you again soon

From the Dodecanese to the Cyclades: sailing off the beaten track!

07/7/2025

Farida B.

Italy

The 10 days on a sailing boat were beautiful. An experience that filled my eyes and heart... it would not have been such if I had not sailed in the company of beautiful people with whom a pleasant connection was created. I thank the "Super Skipper Andrea", a professional: competent, reliable and generous. A holiday that I recommend to those who love the sea and freedom!

From Kalymnos to Samos Dodecanese North on a magnificent 15-meter boat

07/7/2025

Maddalena D.

Italy

A beautiful, regenerating and super positive week. Fabio and Irene welcomed us on Àlisè and immediately made us feel at home. The boat is beautiful, cozy and spacious. Fabio is an excellent skipper, very helpful and reliable, I always felt safe despite the fact that the maltemi never gave up on us and at times it was challenging. Irene was a great co-skipper both during the navigation and in the management of meals and the galley. She was also very helpful and attentive. Great experience. Thanks again

From Rhodes to Kos: the fantastic South Dodecanese

07/1/2025

Patrizia F.

Italy

Going on a boat with Alessio and Anna was a delight, beautiful bays, Alessio always very careful to understand the places to stop and how to please everyone as far as possible. Anna delightful and precious with her tireless energy. I recommend trying it !

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