Thousands of unique sailing holidays, organised by local skippers.

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Top destinations.

Italy

2102 holidays

Greece

644 holidays

Aeolian Islands

396 holidays

Northern Sardinia

342 holidays

Tuscany

341 holidays

Pontine Islands

238 holidays

Croatia

236 holidays

Liguria

162 holidays

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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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