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Choose from 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 2041 available holidays!
Discover your own holiday style. Browse and be inspired

Sailing holidays in Malta: discover the ancient heart of the Mediterranean.

11 available holidays

Dreaming about family sailing holidays? It's time to make that dream a reality.

23 available holidays

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

294 available holidays

Top destinations.

Italy

748 holidays

Greece

293 holidays

Tuscany

163 holidays

Croatia

155 holidays

Aeolian Islands

142 holidays

Northern Sardinia - Maddalena Archipelago and the Costa Smeralda

111 holidays

Pontine Islands

62 holidays

Liguria

57 holidays

Discover all destinations.
from the blog

A sailing holiday is good for you: 5 scientific reasons to prove it.

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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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Still looking for the right holiday ?

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