Exotic sailing holidays with skipper
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.
Catamaran holidays in the Seychelles
Sailing holidays in the Caribbean with a local skipper
Sailing holidays in Thailand with a local skipper
Sailing holidays in Polynesia with Skipper
Catamaran cruise Martinique & Grenadines: sail in paradise!
Caribbean cruise on a sailing boat in Guadeloupe
Catamaran Sailing holidays in Caribbean
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!
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