Thousands of unique sailing holidays, organised by local skippers.

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Top destinations.

Italy

1721 holidays

Greece

607 holidays

Tuscany

344 holidays

Aeolian Islands

284 holidays

Croatia

230 holidays

Northern Sardinia

197 holidays

Pontine Islands

189 holidays

Liguria

131 holidays

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Island hopping in Greece on a sailboat – like a pro: a letter from two experts

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Sailsquare offers an ultimate connection between skippers and travellers.

Skippers create holidays following their passion, travellers will be able to simply enjoy an unforgettable holiday.

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Introduce yourself on Sailsquare, get to know each other on board, go home with new friends.

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You can contact our customer care team, or contact your skipper directly. We're all here to help offer support and guidance!

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