Thousands of unique sailing holidays, organised by local skippers.
Travel alone or in a group, and meet new sailing friends.
Giovanna G. 
Yutian L. 
Berracasa V. 
TERESA Z. 
Peter T. 
Greco P. 
Annamaria R. 
Liuka P. 
Martin A. 
Gulet cruises with skipper and sailing boat cruises
Crewed sailing holidays with a skipper
Catamaran cruise Martinique & Grenadines: sail in paradise!
WWF Sailing Cruises
Sailing cruise in Corsica with skipper
Sailing holidays in Greece with a local skipper
Sailing courses & regatta with professional skipper
Sailsquare Yachts: rent your boat with or without skipper
Sailsquare Yachts offers a detailed selection of sailing boats, catamarans and gulets, from the best charter companies in Italy and in the world, both for experienced sailors who want to rent a boat without skipper and for families and groups of friends who wishes to rent a boat with a skipper for a private cruise .
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!
Try our holiday concierge service!
Can't find exactly what you're looking for? Try our free concierge service! Let us help you find the experience that's just right for you.
Need some help?
Would you like some support using the platform or when making an online payment? We've (almost) always got the answers!
Contact us