Family sailing holidays & cruise trips with kids

Family sailing holidays & cruise trips with kids

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!


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?

sailing holidays family with skipper

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.

skippered sailing holidays with kids

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.

sailing trip family rent a boat with skipper

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 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.

Why you should book a holiday with Sailsquare?

Location point above a wave

The leading sailing holiday marketplace

25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.

Two people with sailor hats

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.

A boat with a magnifier above it

Discover who’s already onboard

Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

Two coins with a currency on top

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!