Why a sailing holiday is perfect for your family and kids?
On Sailsquare there are boats of all shapes and sizes waiting for you and your family to board in a dream destination. Sailing holidays have a unique trait in that how you enjoy the experience can be very different, whether you’re looking for a trip of relaxation, or would like to be more hands-on with the sailing. The art of sailing can be very engaging and enjoyable for people young or old. When browsing holiday experiences, feel free to message skippers to learn more about how children can be involved in the experience.
The age-old myth is that sailing holidays are only for the rich, well-connected, or experienced sailors - but this is no longer the case. Now with as little as €100 you can experience the magic of a sailing holiday weekend, and €400, a full week sailing. Sailsquare is built on sharing economy principles, meaning it connects skippers and curious travellers, which is how such unique experiences are available at such flexible prices.
Travelling on holiday with a family requires a lot of organisation and planning, setting sail on a Sailsquare sailing holiday with an experienced, local skipper allows you the peace of mind of knowing that there is always someone there to offer tips, guidance, and support - along with our Customer Support team who are present via email, live chat, and by phone.
The best sailing destinations and holidays for your next family adventure
Yacht sailing holidays & skippered tours in Tuscany
Yacht sailing holidays & skippered tours in Liguria and Cinque Terre
Private yacht sailing holidays with skipper in Croatia
Private yacht vacations & whole boat skippered cruise
Yacht sailing holidays & skippered tours in Corsica
Yacht sailing holidays & skippered tours in the Aeolian Islands
Yacht sailing holidays & skippered tours in Pontine Islands
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!
Would you like some support using the platform? We've (almost) always got the answers!