Get on board of a vacation with crew and live the sea without
thoughts. Whether you choose a sailboat, a catamaran or a gulet,
comfort and gulet, comfort and well-being will be the first place
for a holiday of absolute relaxation. vacation of absolute
relaxation.
25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.
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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!
We had a truly fantastic holiday with Olmo and Margerita and can recommend it to everybody looking for a nice and relaxing sailing vacation!
Olmo is a very knowledgable sailor, with whom you feel safe at all times and who is also happy to teach about sailing, if desired. Margarita is a very fun person and a great cook. They knew the area very well and adjusted the trip to our preferences, so that we had the best possible experience. Furthermore, are very nice and easy-going people, so that you like to spend time with them beyond the sailing. The boat is also nice and comfortable.
After a stormy start due to the weather we spent a wonderful holiday, the boat has large interior spaces and Francesco is experienced and reliable, he managed to satisfy us on all our requests.
Thank you!!!
A week among crystal clear waters, suggestive coves, romantic towns, ancient hermitages, relaxation and good company. All sailing on Eleda, a sailboat rich in history captained by Cesare, a very capable and experienced skipper, who will tell you endless anecdotes and stories of the sea. In addition, if you wish, it will involve you in the different aspects of navigation.
Together with him you will meet Carla, his companion and precious assistant in all the maneuvers that, with her sunny sympathy, kindness and constant good humor, is a fundamental presence on board.
Every day, between one bath and another, you can enjoy the excellent dishes prepared for you: Cesare has even prepared the tagliatelle made by boat ... with a rolling pin!!!
In short, thanks guys!
We had a really good time, the Dalmatian islands are gorgeous and sailing with you was a beautiful experience.
Good wind!
Maria Cristina & Stefano
First Sailing Experience.
Leonardo is a person who lives the sea at 360 degrees, he transmits this visceral passion.
Visited all the corners, coves and seabed of each island.
Too bad only for not having gone to Ventotene and being back 2 days before, but this does not have weight from him but from adverse weather conditions .
I conclude by saying that surely as in any family after several days many in a small space can be born some friction, but with a good dose of adaptation also passes.
Lucky to have found another very nice and friendly couple.
Great trip reliable and confident skipper. Friendly and welcoming hostess. Boat with large outdoor spaces for pleasant moments of conviviality. The kitchen is also excellent.
I have just returned from my holiday with Gianni to the Ionian islands of Greece. What can I say? He and Giovanna were wonderful. Gianni is a true connoisseur of the sea. Together with my travel companions we lived an experience of joy and safety. He made us discover lovely places with joy and availability. He and Giovanna cooked for us, accompanied us on excursions and we also learned a few more secrets about the winds and navigation. Giovanna amazing! Goliardic and playful climate always. I recommend to everyone!
Roberto is a skipper very prepared and attentive to customer care. I would recommend him for any crossing as he is a guarantee of safety and passion for what he is doing. With him we had the opportunity to see the true face of Ibiza: the non-commercial one but of the 70s hippies, to be clear. An itinerary between Ibiza and Formentera made of magical views, interesting coves and cozy brains with the characteristic bongos.
Unique experience!
Breathtaking scenery on board Rebelle, a brand new boat equipped with all comforts: from the coffee maker to the air conditioning for the hottest nights.
The professionalism, competence, grace and hospitality of Clelia (the skipper) and Simona (as a sailor) made this experience unforgettable.
Felt thanks to them, to my fellow adventurers and to the splendid Sicilian views :)
The places visited were wonderful, the company on board excellent.
Thanks to the high experience and professionalism of Massimo (and Martina) the holiday was beautiful and will be unforgettable.
Quiet navigation, stops without problems, excellent cuisine (I will always remember the dishes prepared - spaghetti mussels and clams, pasta with sardines, zucchini oil and pecorino cheese and many others).
The welcome on board was impeccable.
It was a fantastic week and very relaxing. With the group a beautiful harmony was created and I felt good from the first moment. An added value was certainly the sleep in the harbor for most of the nights: waking up in a bay and immediately taking the first dip before having breakfast has no equal. Thanks then to Claudio and also to Barbara, for being a cook attentive to my celiac needs. I hope there are other opportunities to travel together!
Top week! The skipper Simon was fantastic, he immediately put us at ease and always shared with us the best itinerary often satisfying our requests ... with a lot of patience! We shared lunches and dinners always with so much joy and he taught us the key maneuvers to enter and exit the ports and often helped him with sails. Sleeping in radda is a unique experience... we lived in close contact with nature... what can I say?... super experience!
It was an unforgettable week aboard Kikko, a wonderful boat, very spacious and kept like a jewel, which exudes the passion for the sea that only three fantastic people like Daniele, Mariapia and Andrea can infuse. Daniele is an excellent captain, with him you always feel in good hands, thanks to his experience and his ability to keep the situation under control with a smile on his face. Mariapia is an exceptional cook, she delighted us throughout the week with dishes that are always different and able to satisfy everyone's tastes. Andrea is a very nice guy who at sea, despite his young age, has experience to sell. Together, they make an exceptional trio but above all a sweet family that makes all guests feel at home and in total relaxation. For lovers of water sports, the boat is super equipped and you can experience wonderful places in an even more adventurous way. Thank you for this wonderful experience! Elisa and Michele
Top Holiday!
Where to start... it was a unique experience!
We started from Tropea, and then passed by Panarea, Lipari, Filicudi, Vulcano and Stromboli. We could admire breathtaking landscapes and coves!
Our snorkleing was accompanied by some great and healthy food prepared with care by Rodolfo and Massimo (Captain of Excellence) who managed to meet all our culinary needs. The icing on the cake? definitely the crew! We met fantanistic people. We laughed and danced aboard the lovely Alysia! Extra-recommended experience.
I would do this interesting and wonderful adventure with Adele and Mark again and again and recommend it to my loved one without hesitation! From delicious food with great cocktails, to playing dolphins, loving dadjokes from Mark, shared nightly adventures in the dinghy and Adele's care for us and the right music, to the fight of the crabs vs. jellyfish, everything was just perfect. We go home with the feeling of having taken family holidays with Adele and Mark and being teenagers again. Again and again!
Vittorio and Giulia are two exquisite and genuine people, who have made the boat a life choice. They put the comfort of the guests at the center of their attention throughout the cruise, never missing anything and delighting us with their stories. Despite some small inconveniences (not due to them, and that can always happen at sea), they have always been able to manage the situation in the best way. A mention also to the boat, which is a nice gem, always clean and with the plus of private bathrooms. I can't wait for the next adventure with them!
Fantastic experience, what to say elba always beautiful but this time in particular, the skipper Edoardo and his partner Irene were very good I dare say of the travel companions albeit short.
Edoardo very good and self-confident in steering the boat and Irene an excellent assistant but above all cook.
Experience to be redone as soon as possible
Everything above all expectations
With Andrea in first place, competence and safety at sea. From a human point of view a very special person for the attention he has towards his guests and the ability to better cope with any situation or request. A beautiful week of carefree and fun. Thanks to him and his collaborators, Alessandro and Susanna, see you soon guys!!
What can I say! A very pleasant first experience in the company of Marco and his wife!! My husband and I should have had travel companions but at the last we found ourselves exclusive guests of the tour ... We sailed, chatted, laughed, sunbathed and slept in absolute freedom. We were greeted by a good aperitif which was then followed by an excellent lunch and also a good snack. We felt pampered until sunset and to conclude this beautiful adventure we also thought of the dolphins spotted in packs along the way back ... Thanks Marco!! Good wind and to the next adventure!
It was a very pleasant holiday, Pier and Nicoletta did their best to fully experience the places visited both at sea and on the mainland; even life on board was managed very well and the days have just flown!
Thank you guys for welcoming us in your boat with all its comforts and the precautions reserved for us you have made us this Easter special.
Everything was perfect... The ability of andrea and his partner to sail even with sea always formed in maximum tranquility and carefree the enchanted places visited at the tremiti the walks in the villages evenings and dinners on the boat spent in joy with the fantastic companions ... leave an indelible memory and new true friendships
Thank you for the wonderful holiday
I highly recommend to try all these beautiful emotions
Beautiful sailing experience, exciting chats, great food and above all many bubbles!
Giorgio is a very pleasant, helpful and empathetic person: he managed to involve and make people with significantly different backgrounds and experience feel at ease on board (newbies, experienced skippers and "amateur" enthusiasts) so that everyone could make the most of the experience. His "Clorinda" is a spacious, clean, brand new and full of comfort boat (heating, privacy guaranteed by the excellent closed cabins, soft and spacious mattresses, hot shower in the cabin and on the platform... not to mention the delicious delicacies that he cooked us in the amazing overhead oven!). I recommend to everyone and hope to repeat the adventure soon!
Why choose a sailing vacation with hostess or crew
Do you want to enjoy an all-round relaxing vacation, without having to think about anything? On board these vacations you will find a crew who will brighten up your stay.
Find the perfect vacation for you: choose a vacation with a hostess who will take care of the all-round service or choose a vacation with an on-board chef who will prepare the best local dishes for the guests.
Enjoy the vacation you've been dreaming of for a long time after a year of work: devote your time only to having fun and relaxing, without having to lift a finger.
Are you planning your vacation with children and don't want to have any thoughts other than enjoying time with your family? A vacation on a boat with a crew is ideal!
The best destinations for a sailing vacation with crew
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Sailing vacations with hostess or crew in the Mediterranean: discover the wonders of our sea, following the advice of the skipper, perhaps sipping a cocktail prepared by the staff on board. You'll be spoiled for choice for a cruise on a sailing boat or catamaran or gulet with family, friends or new people met on board. Marinas and marinas, historic and lively villages, islands full of small restaurants or almost deserted islands, waters from green to turquoise, wide beaches and hidden coves: a boating vacation in the Mediterranean offers everything!
Do you prefer to go abroad? Choose a sailing vacation with hostess or crew in Croatia or in Greece, choosing a custom itinerary among the dozens and dozens of islands. But that's not all: Côte d'Azur, Corsica, Balearic Islands are all fantastic experiences, surpassed perhaps only by a vacation aboard a gulet in Turkey with crew for maximum comfort!
Hosted or crewed sailing vacations in the Caribbean: sailing on a catamaran in the Caribbean is the best way to enjoy the winter sea in Martinica, Grenadines, Cuba, Antigua and Barbuda, British Virgin Islands, Guadeloupe: excellent sailing conditions and a unique atmosphere characterize each island of the archipelago. Whether by catamaran or by sailboat, in the Caribbean your skipper will take you to explore small deserted bays even in high season, so that your cruise will be a unique and unforgettable experience.
