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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!

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experiences

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

1709 reviews

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Pack your suitcase and we'll take care of the rest!! Stewards on board!

09/20/2024

Hollie D.

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Australia

Alessandro made us feel seen and safe. He is quiet knowledgeable and did his best to try ensure we were all happy. Recommend
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From Corfu sailing between turquoise sea and white beaches - hostess on board

09/17/2024

Florence D.

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Spain

It was such a wonderful experience! We sailed to some beautiful spots, with crystal-clear water and some incredible shades of turquoise. This holiday is a great way to combine some relaxation: chilling on the deck, sunbathing, reading together with some water activities: SUP, swimming and snorkeling alongside some local culture and entertainment: visiting Corfu town and charming villages, shopping, having dinner in some local restaurants, exploring further by hiking/cycling/driving a scooter on land, Enrica and Omar are the best hosts and they form such a strong partnership. They made sure everything was perfect for all the guests. We all felt totally safe on board with Omar's experience and skills and Enrica cooked some tasty and healthy meals with an Italian touch. The boat was always kept perfectly clean and cosy. I will miss falling asleep to the gentle rocking motions of the sea ! Thanks for sharing your boat with us and for all your kindness!
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Che meraviglia navigare tra Rodi e Kos , cabine con bagno privato

09/16/2024

Philippe H.

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Belgium

Joyeuse croisière de Rhodes à Kos, avec un équipage sympathique. Que du bonheur!
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South of Lefkas, unspoiled nature, bays of Meganisi and myths of Ithaca

09/15/2024

Maurizio C.

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Italy

il titolo della nostra vacanza: una continua sorpresa! A pochi giorni dalla partenza, scopriamo che è stata cancellata dall'armatore per problemi tecnici al motore. Luca di Sailsquare mi ripropone "al volo" un'alternativa che accetto e che ci ha soddisfatto immensamente; lo ringrazio per la sua professionalità! E qui conosco Francesco, una persona davvero professionale, con cui abbiamo avuto la fortuna di condividere la vacanza e la sua barca in maniera esclusiva, essendo io e la mia compagna unici membri dell'equipaggio. Ho potuto veleggiare con la sua supervisione ed accrescere così la mia passione e le mie capacità per la vela, che amo sempre più. Grazie Fra!

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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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