Choose your sailing holiday among thousands of unique experiences
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 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.
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.
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 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.
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
Our favourites
Our collections
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.
Cyclades Islands cruise
07/31/2022
Eva S.
-
France
Guides & tips
The Caribbean archipelago by sailboat
Christmas and New Year 2024 on a sailboat or catamaran
Seychelles by sailboat or catamaran
Norway by Sailing Boat
British Virgin Islands by catamaran
Guide to catamaran interior spaces
The Caribbean archipelago by sailboat
Christmas and New Year 2024 on a sailboat or catamaran
Seychelles by sailboat or catamaran
Norway by Sailing Boat
British Virgin Islands by catamaran
Guide to catamaran interior spaces
Travel with peace of mind
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
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
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.
Let's talk Sailsquare!
Secure payments
© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964