Get on board and sail away: find travel mates on Sailsquare!

Find out in advance who will be on board with you

Browse among several holiday experiences and see who is already on board: name, age, interests, previous experience, all useful info to see who your next travel mates will be.

Get on board carefree: the crew builds up directly on the platform!

You don’t have to be a group to book the holiday of your dreams. With Sailsquare you can get on board and wait for others to join. Book the holiday you prefer and don’t worry about anything else.

Enjoy your holiday and go home with new friends!

There is nothing better than a sailing holiday with the right crew… or maybe there is: go home with new friends to share new wonderful adventures with.

Sailing holidays with Sailsquare: a brand-new experience


Sailing holidays to suit all budgets.

Rumor has it that sailing holidays are just for the rich. Don’t believe it, come and discover a world you’d never thought accessible!

Holiday experiences designed by local skippers.

Sit back and relax. They know their region like the back of their hand!

The adventures of your wildest dream.

Discover sailing, and explore places off the beaten track!

We carry out constant reliability checks, so that you can holiday with confidence.

Traveller feedback

Trust is the basic element of any form of community: for this reason, after each sailing experience we ask the members of the crew to write a review on the holiday and people who were on board, including the skipper… so that you can benefit from their experience.

Secure payments

Fees are collected and transferred to skippers directly by sailsquare within 48 hours after departure. In this way both parties are protected by terms of service.

Experienced skippers

All holidays are organized by experienced and qualified skippers. Also, each new holiday is checked and approved by our staff before being listed.

Join as skipper

Constant support

You can always count on Sailsquare team for any problem, concern or question related to a holiday. Our multi-channel support service is always there for you.

Contact Customer Support

Clear general terms and payment methods

  • Book your holiday by paying via debit/credit card or wire transfer.
  • If you are compelled to give up, find a substitute and you will not lose what you have paid.
  • If a holiday doesn't reach the minimum number of participants, you'll be fully refunded.

Get to know more about Sailsquare


Any doubts? Find the answer here!

It would be my first time on a sailing boat… Is Sailsquare the right choice for me?

If you're passionate about the sea, you like meeting new people and sharing unforgettable experiences, while also keeping an eye on your savings, Sailsquare is the right choice indeed. The holidays you'll find on our platform are very special because they’re created by people like you who want to share their passion for the sea, meet new people and live unique experiences. They are less expensive than those offered by traditional tour operators as they are organised directly by the individual skippers. At the same time, they are safe and transparent thanks to the feedback system on Sailsquare platform. The platform also allows you to learn about your future travel mates. Sailsquare sailing holidays are for everyone: from those looking for a holiday of total relaxation, to those looking for opportunities to learn or improve their sailing skills.

What is Sailsquare about?

Sailsquare is a marketplace where private skippers can post their sailing holiday experiences and where sun and sea lovers willing to meet new friends can find the perfect holiday solution, whether for just a weekend or for a week. We want to make the organization of sailing holidays easier, more reliable and effective day by day, by connecting people who want to share the same exciting experience.

Is it a reliable service?

sailsquare offers you a trustworthy and professional service. All holidays are organized by private boat owners or skippers who are enabled to list their experiences only after a careful selection process. The profiles of all users, as well as the email addresses and Facebook accounts, are verified and matched to real people. Also payments are safe because they are directly managed by Sailsquare, using reliable online payment systems.

Is the service free?

Signing up for sailsquare is completely free of charge. totally for free. As a skipper, you can also list your holidays for free. sailsquare will take a commission on fees for the holiday you book (5%) as well as a commission on the free that goes to the skipper.

What type of holiday can I find on sailsquare?

All holidays listed on sailsquare are created and organized by private users registered on the platform, therefore every holiday is a unique experience. You will find holidays where relaxation is the key element, flotillas for young people, holidays with children, special events, regattas, experiences that combine complementary activities such as diving or trekking. sailsquare provides users with the tools to organize their holiday, collects participation fees and gives assistance, but it’s not directly involved in the actual organization of the holiday.

Which boats are used for the holidays?

Most of the listed holidays are organized by skippers who own their own boat, that they maintain with care and dedication. Sailsquare requires skippers to verify the conformity with current laws and to have a boat in a well-mantained status. In some cases, the boat is chartered by the skipper. Sometimes the boat is chartered through Sailsquare partners.

Who are the skippers?

The skippers on sailsquare are expert sailors who have chosen to organize their holidays through platform, enabled by sailsquare after a careful selection process. In most cases, the skipper is also the owner of the boat. Visiting the skipper's profile page, you will be able to see his/her experiences and skills. You can get an idea of the type of holidays he/she likes to organize and read the reviews on his/her previous holidays. For any question you may have you can also contact your skipper directly.

Are payments safe?

sailsquare is responsible for collecting participation fees, and for transferring the amounts to the skipper, thus ensuring the security of transactions and compliance with the payment terms and the applicable cancellation policy.