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Yacht sailing holidays & skippered tours in Greece

The Greek Archipelago has over 16,000 km of coastline, with many beaches that run for kilometres, a host of secluded bays and coves, and a rich variety of wildlife. Some say the best sailing waters in the world can be found in Greece!

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

10/19/2025

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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CYCLADIC ESCAPE - Active Holidays: 5 days Sailing & Exploring Unknown Greece  

10/18/2025

Tina F.

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Germany

I very much liked the Mixture of sailing, stops for swimming, attractions and good food in the Taverns. The boat was very comfortable and well-equiped. Orestis Was very friendly, Attentive and professional. It was perfect and I would love to do another Trip in future.

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Guides & tips


Greece

Ionian Islands, Cyclades Islands and Dodecanese are just some of the most beautiful destinations for a sailing or catamaran vacation in Greece
Guide to Greece by sailboat

Ionian Islands

Paxos, Zakynthos, Kefalonia and Lefkada are just some of the best destinations for a sailing or catamaran vacation in the Ionian Islands.
Guide to Ionian Islands by sailboat

Cyclades islands

Sandy beaches, small bays and blue and white villages have made the Cyclades a world-famous landscape, perfect for exploring by sailboat or catamaran.
Guide to Cyclades islands by sailboat

Greece: the most beautiful places to sail

Greece: departures by month

Other travel ideas

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