Thousands of unique sailing holidays, organised by local skippers.
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Pierre Or Panos D. 52 minutes ago
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Pierre Or Panos D. 54 minutes ago
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Pierre Or Panos D. 54 minutes ago
Pierre Or Panos D. 54 minutes ago
Top destinations.
Italy
2042 holidays
Greece
667 holidays
Tuscany
371 holidays
Aeolian Islands
356 holidays
Northern Sardinia
319 holidays
Croatia
253 holidays
Pontine Islands
203 holidays
Liguria
151 holidays
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!
Still looking for the right holiday ?
You have some idea of your perfect holiday, but can't find what you're looking for? Get in touch! We can find the right experience together!
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Would like some support using the platform or making an online payment? We've (almost) always got the answers!