Family sailing holidays with a local skipper
It is the best environment and relaxed atmosphere to spend time with family, and create long-lasting holiday memories. Can you travel with children? But of course! Sailing offers children the opportunity to engage with operation of boat, and most importantly have fun in doing so!
BEST PRICE GUARANTEE
If you find the same experience for a lower price elsewhere, we’ll match the price.
Why a sailing holiday is perfect for your family and kids?
Fun for adults and children alike
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.
Dream holidays that work with your budget
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.
Holidaying peace of mind
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 piece 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
Sailing holidays in Tuscany with a local skipper
Sailing holidays in Liguria and Cinque Terre
Hire a whole boat with skipper in Croatia
Hire a whole boat with skipper
Sailing cruise in Corsica with skipper
Sailing holidays in Aeolian Islands with a local skipper
Sailing holidays in the Pontine Islands with skipper
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
Would you like some support using the platform? We've (almost) always got the answers!
Call us at +44 20351 44220
Check out our Help page