
Nicola M.
review about Let's learn how to sail a boat September 2022
Discover the magic of sailing holidays! Hire a whole boat: a new way of traveling with your loved one, friends or family. Find your dream adventure among thousands of holidays from the Mediterranean to the Caribbeans.
The leading sailing holiday marketplace
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!
review about Let's learn how to sail a boat September 2022
review about Between the Aeolian Islands and Capo Milazzo September 2022
review about Eolian Sailing- Max 4 guest for exclusivity and relax - Hostess on Board August 2022
review about In the sea of Ulysses! Discovering the most beautiful islands August 2022
review about Last minute Ponza and Palmarola on 52 feet August 2022
review about Weekend on the island of Capraia July 2022
review about To the Aeolian Islands on a 14 mt with Gabriella -skipper and mum- and Nicola -seaman and companion of adventures- July 2022
review about Blue Summer Week Flegree and Pontine July 2022
review about Elba island: beauty and relax July 2022
review about Sailboat cruise through the South Dalmatian islands July 2022
review about Egadi Islands: a dream between sea and land June 2022
review about Weekend of sailing and sea in the Gulf of Trieste (with yoga teacher on request) May 2022
review about Sailing between the Costa Smeralda and the Maddalena Park May 2022
review about Sailing for the Argentario, Giglio and Giannutri ... a perfect week July 2021
review about We celebrate Easter on Elba April 2022
review about North Sardinia islands on a magnificent 15 meter boat September 2021
review about From the Zingaro reserve to the Egadi islands: sailing to discover north-western Sicily August 2021
review about Northern Sardinia and Southern Corsica on an exceptional 47-foot sailboat for 4 privileged people August 2021
review about South of Lefkas between pristine nature bays of Meganisi and myths of Ithaca July 2021
review about two hearts and a sailboat | weekend for couples to discover the Flegrean islands August 2021
review about Full Charter - North Sardinia and Corsica July 2021
review about A dream for two ... Elba and its magic, bays and coves! July 2021
review about The ideal holiday among the 7 pearls of the Tyrrhenian Sea in a true unspoiled paradise - Hostess on board July 2021
review about Between Elba and Corsica-Boat 14 meters exclusively for 4 guests-Hostess on board. July 2021
Would you like some support using the platform? We've (almost) always got the answers!
Use our free holiday concierge tool - and let us find your dream sailing experience for you!
Let's find it together!A sailing holiday offers an ideal setting to get together as a family and share special moments in serenity. Sleeping under the stars and a clear sky, taking the helm of the boat, sailing from island to island and waking up each morning in a new paradise are all wonderful components of sailing holidays that your family can share and create lasting memories.
Booking an entire sailboat with a skipper is a great option for groups of friends wishing for an original holiday. Diving, exploration, dinners, sunsets, parties under the stars - all of the ingredients for an exceptional adventure. Choose how involved you want to be in the sailing - whether you’d prefer to learn about sailing, or simply relax and enjoy the blissful atmosphere and scenery, embarking on a sailing trip with a skipper allows you ultimate holidaying freedom.
Some skippers offer experiences with other crew members - this might include a hostess or chef. Such listings are designed to offer holidaymakers another level of relaxation and comfort during their trip. If you are looking for an experience as worry free, with a little bit more luxury, consider a whole boat sailing holiday reservation with a crew.
There is no best specific period to rent an entire sailboat. Whenever you are looking for a sailing holiday, you can find whole boat booking options. The availability follows the seasonal peaks - for example, you can find a host of whole boat hire options through the European summer in the Mediterannean, and a host of options in the Caribbean and Indian Ocean during the European winter.
By booking the entire boat with a skipper, you can save up to 50% in comparison to the total sum of the individual spot price. The prices vary according to the period, the destination, and the type of boat. You can find periods of a week in the Mediterranean with skipper from €1,800.
Booking an entire sailboat is possible across the world. You can rent a catamaran with skipper in the Caribbean and discover the paradisiacal islands - or you can opt to rent a skippered sailboat in the Mediterranean where the coastlines offers countless beautiful destinations and itineraries.
There is a sailing experience available for all. If you are in need of a little help to find the right holiday for you, you can use our holiday concierge service for free.
You can find whole sailboats in all the seas of the world, at all different budgets and for all different tastes. Charter a whole boat with a skipper in the Mediterranean: discover the wonders of the sea, venture to the lesser known beaches and coves. The Mediterranean is shared by many countries, and has many stunning coastlines that make for some of the best destinations for sailing holidays in the world. Cities, towns, and villages home to a long history and rich culture, with picturesque natural wonders, with turquoise waters. The Côte d'Azur, Corsica, the Balearics, Greece, and Croatia - just to name a few!
Renting a skippered sailboat in the Caribbean: set sail aboard a catamaran in the Caribbean and discover the magical islands of Guadeloupe, Martinique, Grenadines, Cuba, San Blas, British Virgin Islands, and the Bahamas, where there are excellent sailing conditions, and in a unique atmosphere of relaxation and easygoing that is shared across the archipelago. This experience is topped off by the fresh, local cuisine of the area - that acts as an integral role of the experience. Whether you travel by catamaran or sailboat, your skipper will lead you to the special destinations of the region, making for a unique and unforgettable holidaying experience!