How about a warm winter sail in the Caribbean or the Seychelles? We have got you covered.

Escape the cold, and experience true blue waters. Find your exotic winter holiday on Sailsquare.

This winter get aboard a sailboat, and discover exotic islands and clear warm waters. Swap your boots and scarf for goggles and swim-gear!

A winter break is a great way for solo travellers, couple, and families to break out of normality, and enjoy an adventure in the sun.

At Sailsquare we're passionate about connecting people, and enabling unique, once-in-a-lifetime experiences. Search through our platform using the search tabs that best suit match your desires. and get to know with your future skipper before you book!

Caribbean islands on a sailboat, the experience of a lifetime.

From San Blas cayos to the Virgin Islands, from Tobago to Martinica: there are many places where you can experience the holiday of a lifetime! You will find warm water, crystal clear, perfect to see the exotic fish, you will love it!

And don’t forget great food, great wine and meeting new friend, this is all part of the experience!