Crewed yacht sailing holidays & tours in Italy

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!