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Whole boat with skipper yacht sailing holidays & tours in Dodecanese

Discover more than 1 opportunities to get on board a Whole boat with skipper adventure in Dodecanese. A unique experience with a local skipper, starting at €350 a week.

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The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

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

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 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

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 - Whole boat with skipper yacht sailing holidays & tours in Dodecanese

37 reviews

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

10/22/2025

Douglas B.

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United Kingdom

An extraordinary experience that exceeded all expectations
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Secret Aegean with skipper and kitchen on board - Rhodes to Kos

10/19/2025

Catherine S.

My first sailing experience was simply extraordinary! ⛵️ Unforgettable moments spent at sea, surrounded by incredible people. Anna Lisa and Emmanuel were amazing hosts! Thank you to everyone for your good humor, your kindness and this unique adventure. Can't wait to do it again! 🌊✨
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Secret Aegean with skipper and kitchen on board - Rhodes to Kos

10/19/2025

Olivier P.

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France

Some sailings leave a softer trace than that of the boat's wake. The sailing week was perfect: beautiful sailing, delicious food and a friendly atmosphere. Thank you to them for this wonderful interlude — I will leave without hesitation!
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From Samos to North Dodecanese Kalymnos on a magnificent 15-meter boat

09/16/2025

Bruno P.

We had a great time aboard the Alizé! As the other passengers have already indicated, Fabio and Irene, thanks to their professionalism, their kindness, their attention to detail and also (this is important! :)) their delicious dishes, allowed us to enjoy a week of happy disconnection. They quickly understood what we liked (fishing, sailing, hiking and discovering the beautiful Greek islands) and adapted the program accordingly. For us, we didn't spend a week with two strangers, but with friends. See you next year!

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