Sailing yacht weekend breaks & getaways

Sailing yacht weekend breaks & getaways

A sailing weekend to discover the charm of life on the sailing boat and the beauty of the sea. Two days will be enough to feel regenerated and want to get back on board to discover new landscapes.


If you find the same experience for a lower price elsewhere, we’ll match the price.

Why book a weekend sailing trip?

Vacanze in coppia in barca a vela

Sail and take the last baths

It is ideal for reviving from the work of the week, freeing the mind and suddenly feeling at peace with the world. The only noise other than that of the sea will be laughter in the cockpit and chatter on deck under the stars. Two days will be enough to believe that you have been away much longer and to choose to return aboard, but this time for a full week's vacation.

Vacanze di coppia in barca a vela

Discover Italy...from the sea!

A nice way to visit the Italian coasts arriving from the sea and not as usual from the land! A "trip out of town" different from the usual to discover places and spectacular beaches, which perhaps you have always given up because they are difficult to reach if not from the sea. Two days or a long weekend of sailing will make you discover the fascination of life on a boat and the beauty of the sea, making you change perspective.

Fuga romantica in barca a vela

Weekend in couple, with friends or single

Looking for a special idea to spend the weekend with your better half? Nothing is more romantic than a weekend sailing in coppi watching the stars from the deck. And why not do it with friends instead? Forget the stars, turn up the volume and enjoy the party! If you're on your own, however, hop aboard for a single sailing weekend and come home with lots of new friends...even better if it's a flotilla weekend!

Why you should book a holiday with Sailsquare?

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25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.

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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.

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Discover who’s already onboard

Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

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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!

8 reasons to take a weekend sailing trip

  • Whether you are single, in couple or in company is a different opportunity to meet new people and enjoy a weekend in total relaxation.
  • Regenerate your body by filling up with clean air, iodine for the lungs, vitamin D for the bones and clear your mind of all thoughts. Mooring and getting away from the earth will make you feel light.
  • Experience the thrill of being at the helm and maneuvering guided by experienced skippers. For first-time sailors, a weekend on a boat is the best way to get to know the world of sailing and perhaps take a sailing course.
  • Choose the experience you like best and cultivate your passions on board. There are, in fact, many proposals to be selected according to the activities: from a sailing-trekking weekend to yoga, all in the name of Sport & Wellness.
  • There are events that lived from the boat have a whole other flavor. A weekend to live as protagonists participating in the Barcolana of Trieste, the Feast of the Redentor of Venice, the Sagra del Totano di Capraia and many others.
  • At April, May and during the Easter holidays, a weekend sailing in the spring will be a great way to start to enjoy the sea and the summer.
  • In contrast, a weekend sailing in September will make you feel still on vacation. The heat not sultry, warm water and sea breeze will keep you company and make gradual impact with the everyday and the new working year.
  • Make the future bride and groom a unique experience: a weekend on a boat for a hen or stag party is the perfect combination of relax and party, between intimacy and goliardia, between novelty and excitement! You can rent a whole boat for a weekend at a super affordable price.

Sailing weekend in Liguria

Week end in eastern Liguria to discover its seaside villages. Sailing between the Gulf of Poets, the island Palmaria, Portovenere, Lerici with its fortress castle. And then the Five Lands, discovering polluted places and romantic coves that attract tourists from all over the world. You can travel by land in one direction and then admire all the beauty from the sea to return back, relaxing on the deck of your sailboat.

Sailing weekend on the French Riviera

Week end on the French Riviera starting from San Remo towards Menton, Montecarlo and Nice. A mini cruise immersed in the colors and scents of the Mediterranean. Breakfast ashore with a fragrant croissant, then set sail to discover the turquoise waters and clear that gave its name to this area.

Weekend in Tuscany by sailing boat

Week end in Elba Island and Capraia, discovering the villages and the most beautiful bays of the Tuscan Archipelago. An opportunity to spend a weekend different from the usual in the name of nature, trekking and sailing. A perfect destination for a weekend sailing.

Weekend sailing along the Argentario to the island of Giglio and Giannutri. Two days of relaxation on a sailing boat surrounded by a turquoise sea and secret coves. Discover the freshest fish in one of the local restaurants, then marvel at the beauty of these underwater places by snorkeling in their waters.

Weekend in Pontine Islands by sailing boat

Week end in the Pontine Islands between Ponza, Gavi, Palmarola, Ventotene, Zannone and Santo Stefano. A sailing experience to regenerate between nature, fun and relaxation, easy and convenient option for a weekend from Rome.

Sailing weekend in Campania

Week end in the Gulf of Naples. A mini cruise sailing in the Campania archipelago between Ischia and Procida, among breathtaking landscapes and places rich in history. With the Vesuvius always in sight, discover this strip of land from the sea.

Week end on the Amalfi Coast: two days sailing between Capri and its Faraglioni, Sorrento, Positano and Amalfi. If the Coast is famous among tourists for its streets, it's even more famous for its waters! Nothing can beat a VIP-style entrance among the stacks of Capri sailing, between yachts and paparazzi.

Weekend in Sicily sailing

Week end to the Aeolian Islands sailing among the conical shapes of volcanoes and sinking your feet into the black sand of Stromboli, Salina, Lipari and Panarea. With cheap off-season flights from every city to Sicily, this is a perfect destination for a spring or fall weekend sailing so that summer never ends!

Week end to the Egadi Islands, discovering what is probably the most beautiful sea in Italy that laps the coasts of Favignana, Levanzo, Marettimo. A weekend of pure relaxation!

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