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Sailboat yacht sailing holidays & tours in Dodecanese

Discover more than 6 opportunities to get on board a Sailboat adventure in Dodecanese. A unique experience with a local skipper, starting at €350 a week.

Why book a holiday with Sailsquare?

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 - Sailboat yacht sailing holidays & tours in Dodecanese

201 reviews

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Rhodes Kalymnos South Dodecanese on magnificent 15-meter boat

08/24/2025

Valentina B.

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Italy

We spent a wonderful week aboard Alizé, a boat very well cared for by Fabio and Irene and well equipped by them to ensure both safety and comfort for the crew. Fabio has shown great experience at sea, the one that humble, true captains have, with deep respect for the sea. His curiosity led him to delve into the history and beauty of the Greek islands, so as to be able to give us excellent advice and make us enjoy the places visited to the fullest. Irene with discretion and sweetness made us feel at home, always very careful to make us feel good and not to miss anything. Always professional and attentive, nice and engaging, they made the trip safe and fun. We visited wonderful coves and corners of land, always feeling in excellent hands. An experience and crew that we really ☺️ recommend
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Kalymnos Rhodes Dodecanese South on magnificent 15-meter boat

08/23/2025

Marco B.

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Italy

Elegant and spacious boat with excellent marine performance. Skipper of considerable experience and professionalism. Fabio and Irene, friendly and welcoming, made us discover the most characteristic bays, with stories of the places and very apt suggestions. Highly recommended, experience to be repeated.
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Secret Aegean with skipper and kitchen on board from Rhodes to Kos

08/10/2025

BARBARA C.

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Italy

Excellent experience both as a proposal for the various destinations visited and for the culinary aspect! Yes, you eat and surf well on MIVIDA! Interesting and well organized shore excursions!
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From Rhodes to Kos: the fantastic South Dodecanese

08/3/2025

Riccardo M.

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Italy

too much engine too little sail

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