Live unique experiences, meet like-minded people,save moneyand, travelsafe.

Get on board and cast off: you can find your 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!

It is not necessary to have a group already formed to book an experience: what is great about Sailsquare is the possibility to get on board on your own and wait for others to join. Choose the holiday you prefer and book your spot without overthinking too much!

Enjoy your holiday and get back home with new friends!

There is nothing better than a sailing holiday with the right crew… or maybe there is: getting back with many new friends with whom you can share new wonderful adventures!

Sailing holidays with Sailsquare: a totally brand-new world

Sailing holidays: terrific experiences to suit all pockets

Rumor has it that sailing holidays are just for Rockefeller, but don’t get stuck in prejudice and discover a world you would have never thought to be accessible!

Holiday experiences created directly by skippers: a unique and cheaper choice.

On Sailsquare, skippers are the creators of their own experiences. This means having a passionate and expert person on board who can make you live unforgettable experiences, as well as making you save some money.

Less intermediaries: the secret ingredient to respect your wallet

Sailsquare works with the values and principles of sharing economy, providing the platform and the service... a lean and effective structure, as well as cheaper, of course.

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

User feedbacks

Trust is the basic element of all communities: for this reason, after every experience we ask all members of the crew to leave a review about the holiday and people who were on board, including the skipper… so you too can benefit from their experience.

Secure payments

Fees are collected and transferred to skippers directly by Sailsquare within two working days after departure. In this way both parties are protected by terms of service.

Experienced skippers

All holidays are organized by experienced skippers who own the necessary licenses to steer leisure boats. Moreover, all new holiday experiences are checked and approved by our staff before being published.

Join as skipper

Constant support

For any problem, concern or need in the organisation or participation in a holiday, you can always count on us: a multi-channel support service is always there to side you.

Contact our Customer Support

Book your holiday in just 4 clicks!

Clear general terms and payment methods

Book your holiday via credit or debit card.
If you are compelled to give up, find a substitute and you will not lose what you have paid.
In case a holiday does not reach the minimum crew requested to start, you will be fully refunded.

Get to know more about Sailsquare

Have some doubts? Here you can find the answer!

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

If you love staying in close contact with the sea, meeting new friends and share with them an unforgettable experience while keeping an eye on your savings, Sailsquare is the right place for you. Holidays on our platform are special because they are created by people like you who want to share their love for the sea, new encounters and one-of-a-kind experiences. On one hand, they are cheaper than those offered by traditional tour operators as they are organized by individuals. On the other, they are safe and transparent thanks the feedback system, that can make you discover in advance the features of your next travel mates. Experiences on Sailsquare are truly for everybody: from those searching for a total relaxation holiday with mask and snorkel to keep company, to those looking for sailing experiences to practice sailing skills.

What is Sailsquare about?

Sailsquare is a market-place 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 us, using reliable partners recognized at international level.

The service is free?

Signing up for Sailsquare is totally for free. You can also list for free a holiday experience. Sailsquare requires the payment of a commission on gathered fees for holiday booking (5%), as well as keeping a commission on the fee given to the skipper after a booking by the user from the platform

Which types of holiday can I find on Sailsquare?

All holidays posted 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 holiday's organization.

Which boats are used for the holidays?

Most of the listed holidays are organized by skippers that own a boat, maintained 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 other cases, the boat is rented by the skipper. Sometimes the boat is rented through Sailsquare partners.

Who are the skippers?

The skippers on Sailsquare are expert sailors who have chosen to organize their holidays using the platform, enabled by Sailsquare after a careful selection process. In most cases, the skipper is also the owner of the yacht for the holiday. By visiting the skipper's public profile page, you can read about his/her experiences and skills, get an idea of the type of holidays he/she loves to organize and read the reviews of the users he/she's been on vacation with. For any curiosity you can contact his/her directly and ask all the necessary information about the holiday you are interested in.

Payments are safe?

Sailsquare is responsible for collecting holiday's partecipation fees, and for transfering the amounts to the yacht owner, thus ensuring the security of transactions and compliance with the payment terms and the applicable cancellation policy.

View all frequently asked questions.