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Yacht sailing holidays & skippered tours in Greece

Discover more than 3 sailing holidays in Greece. Book a spot onboard and live 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 - Yacht sailing holidays & skippered tours in Greece

1904 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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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

10/19/2025

Jean-Loup N.

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Switzerland

Hello! We had a wonderful time with Andrea and Marta around the islands of Corfu, Paxos, and Antipaxos, discovering their hidden gems. The boat was spotless and spacious (we were five on board); everything was perfectly taken care of, and all I had to do was relax on the deck. As is often the case in the Mediterranean, sailing conditions aren’t always ideal, and our skipper preferred using the motor rather than the sails — which made the trip smooth and relaxing as we cruised from one beautiful anchorage to another. A special note for fans of the Netflix series Maestro in Blue: you might even come across the filming set — or the director and crew — during your cruise! Thank you again, Andrea and Marta! Cheers!

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