header cover

Choose your sailing holiday among thousands of unique experiences

<b>Unique</b> experiences, suitable <b>for all</b>

Unique experiences, suitable for all

Live, even if you have no experience, the unique thrill of a sailing holiday. Choose from thousands of sailing holidays worldwide offered by passionate skippers and selected local organisations.

Holidays for <b>singles</b> and <b>small groups</b>

Holidays for singles and small groups

Whether you want to set off alone and meet new people or enjoy unforgettable moments with your friends, the only thing you need to bring on board is the desire to live an experience in touch with the sea and nature.

<b>Sustainable</b> tourism

Sustainable tourism

For more than 10 years, we have been working to spread an environmentally friendly way of experiencing the sea and are committed to the preservation of the sea and its inhabitants.

Flexible Cancellation

Buy the extension to cancel your booking until your departure!

Our favourites

Memories from our community

A global community

Over 150,000 people from 80 countries already joined our community of travellers and skippers, united by the desire to discover other people and the sea, leaving 28,000 reviews. The average rating is 4.8 out of 5.

trust wrap image
avatar image

Cyclades Islands cruise

07/31/2022

Eva S.

-

France

The skipper, Alexandros, with his mastery of going to sea and his friendliness, made our holiday flawless. His boat is comfortable, modern and spotlessly clean!

Travel with peace of mind

Total transparency

Total transparency

Want to avoid surprises? Find out before you book who your skipper and fellow travellers will be. Do you have questions or doubts? Send a message to the skipper!

Flexible cancellation

Flexible cancellation

Cancel within 30 days of departure for any reason and receive a full refund. Want even more? Purchase the extension to cancel your booking until your departure.

Constant support

Constant support

Our dedicated multilingual support team is always ready to assist you, before and during your holiday, and is always in touch with the skippers we work with.

Can't <b>find the perfect holiday</b> for you?

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964