Sport & Wellness sailing holidays & skippered tours
Do you like to relax but at the same time need to stay active?
active? You can enjoy a week or a weekend of Sport & Wellness.
Choose from dozens of activities such as sailing, hiking, yoga,
snorkelling and, of course, sailing and, of course, sailing.
25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.
Get onboard solo, with your family, or your friends
Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.
Discover who’s already onboard
Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.
Sailing holidays that suit all budgets
Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!
Reviews - Sport & Wellness sailing holidays & skippered tours
Skipper Mario has a great experience and has always made us feel in very good hands. At our request, he was very helpful in letting us participate in the maneuvers and conducting of the boat, allowing us to enjoy the beautiful sailing crossings, even arming the Gennaker when the wind and the route allowed it. He and his partner Antonella are of excellent company and, between dinners and evenings in the cockpit sipping a glass of wine, they have established a cheerful and convivial atmosphere, which has made the holiday truly unforgettable for all the crew :)
Beautiful experience, with a particular skipper who combines sailing skills with the passion of freediving and underwater fishing. We were lucky to have 3/4 hours of wind every afternoon to sail. Do not forget the presence on the boat of the excellent cook Renzo.
Traveling by sailboat with Mattia and Laura was really a beautiful experience.
For years I wanted to take a holiday on the island of Elba and as the first time we chose to live it from the sea, it was a beautiful idea.
Mattia and Laura are two very helpful people and that make you feel immediately at ease, we found ourselves very well and it was nice to share aperitifs and lunches on board, all accompanied by the beautiful sea they had around.
We participated in the excursion with the Biodivers center of Porto Azzurro was magnificent, personally I had never seen such a breathtaking seabed full of fish and marine vegetation!
It was a fantastic weekend, we thank you guys for everything you shared with us about this beautiful island.
Until next time!!!
Good wind!
Silvia and Luciano
Tommaso and Laura are two very pleasant and welcoming people. and caring. They have a great passion for the sea. Skipper very attentive and prepared. Excellent their vegan cuisine, which they made us discover with simple but tasty and very varied recipes. On days of bad weather, when unfortunately we were forced to stand still in port, they organized tours by rental car. All great and highly recommended.
Very relaxing and fun holiday.
Roberta was a perfect Captain, attentive and scrupulous during the navigation and with the guests on board.
I recommend without delay to travel with her.
The boat is comfortable, clean and tidy!
I must say that the holiday met expectations
Beautiful experience, although it was my first sailing holiday Joshua and the rest of the group were of great company and hospitality, absolutely recommended!
Relaxing day of sun and sailing. Mirco is an extremely helpful person towards his guests and attentive to their needs. We were absolutely comfortable. Highly recommendable.
Season still cold but when you need a holiday you go ...
The weather was not on our side but the attentive and professional reliable crew made these cold days of March a beautiful experience.
Mario precise and available to our many requests. The boat is spacious, well equipped and well maintained in its interior.... with the new sails it will be super!
Although the climatic conditions have changed the program forcing us to limit the movements at sea, the experience, the sympathy and generosity of Nicola have made the holiday very pleasant and absolutely to be repeated!
To color the experience the maritime stories of Nicola and Salvatore who have been able to excite and entertain the entire crew!
Absolutely to be repeated!!
Expert skipper, great historical, political and social culture of Greece. He knows all the excellences present in the territory, a great connoisseur of wines and typical foods. Great cook and organizer. He was a great colleague for organizing holidays out of standard.
Beautiful weekend! Perfect tour from every point of view: Marco and Cristina are very professional and pleasant and have put everyone at ease, providing all participants with many notions on sailing techniques. Boat kept in excellent condition, clean and comfortable.
The good weather and great company were the icing on the cake to make this holiday a real escape of reality!.
Experience a must do!!
trekking and night in the tented camp on Vesuvius and then sailboat .....
The guide named Stefano and the skipper Alessandro ... I would say great and very fun !!! To the next adventure ......
Leo was a skipper available from the beginning to facilitate the organization of the trip and during the holiday he showed us his competence and perfect knowledge of the places. Then the sympathy and the feeling did the rest... (also good food). great experience, which I recommend.
I speak on behalf of 5 friends who have had the pleasure and fortune to share this experience with Daniela and Enrico.
The whole thing was just perfect.
For some of us it was the first time but we all immediately found ourselves very well with the crew and the spaces of the boat.
Delicious snacks and the cuisine of Daniela who has never made us miss anything from a culinary point of view always satisfying what were our needs.
The boat is very nice and clean and we immediately felt at ease.
The crew has decades of experience in this kind of charter and you can see from how they treat guests and how the day is organized to maximize the experience on board and not lose even a second of the little precious time you have.
Enrico is also a deep connoisseur of both the sea and local history so there is never a lack of dialogue to learn more about the area.
The experience with Vincenzo was very positive. He is a very helpful and nice person. He took us around the gulf showing us the beauties of Liguria. We spent some beautiful days between baths, a visit to the villages on the sea and inevitable aperitifs and meals.
He was very attentive and explained to us the details of the operation of the sailboat making us actively participate in the management of the boat and the maneuvers.
a suitable definition for Romulus would be
"the skipper friendly and great storyteller"
present, courteous, helpful, extremely professional!
my niece and I are really excited!
thanks to romulus and esther
In one word, a "fantastic" day that is all superlative!!! Umberto, the skipper, as well as being a very kind person and an excellent cicerone, is also an excellent cook. A tip ..... TRY WITHOUT HESITATION
ps: a greeting to my travel companions :-)
With Giulio I found myself very well, all week he explained the sails and limited the engine to the only entry into the port or at anchor, always available to take us to shore with the tender, also an excellent musician and singer, a superlative evening at anchor in Lavezzi accompanied by music and the beautiful songs of his repertoire.
Bravo Istvan, you have fully met our expectations! You made us have fun and dream on your boat with attention to detail!
Next year we will definitely come back on holiday with you, prepare us a relaxing and interesting itinerary!
Gérard and Maéva were attentive and caring hosts for our family. They really knew how to meet our wishes and organized the week according to our requests, all with a constant concern for safety at sea. It was really nice. Thanks to them, we spent a great week by boat discovering the best "swimming" spots in Malta and were spoiled by the small dishes of Maéva. All with the good mood of Gérard. The children loved, in short, a stay that we recommend of course !!!!
