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Thousands of unique sailing holidays, organised by local skippers.

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Travel alone or in a group, and meet new sailing friends.
Discover the other 3936 available holidays!
Discover your own holiday style. Browse and be inspired

Sailing holidays in Croatia: discover the islands, islets, and reefs of the Croatian Archipelago.

233 available holidays

The Balearic Islands

246 available holidays

Sailing holidays in Greece: discover the thousands islands of the Greek Archipelago.

606 available holidays
Flotillas on a sailing boat: the best 50 experiences. See all Flotillas experiences.

Top destinations.

Italy

1772 holidays

Greece

606 holidays

Tuscany

363 holidays

Aeolian Islands

289 holidays

Croatia

233 holidays

Northern Sardinia

206 holidays

Pontine Islands

200 holidays

Liguria

122 holidays

Discover all destinations.
from the blog

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.

Discover who is already on board before you set sail!

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

We're here to help you before, during and after your holiday.

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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