Best exotic sailing holiday destinations

Discover the magic of sailing holidays in exotic destinations! Get onboard with a local skipper and live a unique adventure with your crew: learn to sail, explore incredible places, recharge your batteries and experience the local culture & gastronomy.

BEST PRICE GUARANTEE

If you find the same experience for a lower price elsewhere, we’ll match the price.

Paradise on a sailing boat with All Inclusive

Yacht sailing holidays & skippered tours in the BVI

45 holidays

Catamaran yacht sailing holidays & tours in the Seychelles

75 holidays

Yacht sailing holidays & skippered tours in the Caribbean

269 holidays

Yacht sailing holidays & skippered tours in Thailand

36 holidays

Yacht sailing holidays & skippered tours in French Polynesia

78 holidays

Yacht sailing holidays & skippered tours in Grenadines & Martinique

81 holidays

Yacht sailing holidays & skippered tours in Guadeloupe

46 holidays

Catamaran yacht sailing holidays & tours in the Caribbean

255 holidays

Why you should book a holiday with Sailsquare?

The leading sailing holiday marketplace

25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.

Get onboard solo, with your family, or your friends

Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.

Discover who’s already onboard

Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

Sailing holidays that suit all budgets

Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!

Customer Support

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Call us at +44 20351 44220 Check out our Help page