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Sailing and Catamaran Holidays for Families

Exploring the turquoise waters of the Mediterranean's most beautiful archipelagos by sailboat is a magical experience for the whole family. Each day becomes an unforgettable chapter of a sea adventure immersed in nature: children have fun exploring pristine bays, swimming with fish, learning to sail, while parents relax in complete serenity.

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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailing and Catamaran Holidays for Families

568 reviews

Sailing paradise in Greece on a big 50 ft boat: the best local experience

10/6/2026

Iris D.

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BE

Such a wonderful experience! As a solo traveller I had a great time during this trip, Aga and Arnon were very welcoming and took good care of us. The places we visited were stunning, the food Aga prepared for us was excellent, and the overall vibes were 10/10.

Aeolian Islands: between sea and authentic flavours

10/5/2026

Giorgia P.

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IT

Wonderful experience!! Well maintained boat; very comfortable to have a bathroom available in each cabin. The tour allowed us to visit enchanting places, swim in crystal clear waters and enjoy excellent fish dishes and exquisite desserts. Carlo, our skipper (Merchant Marine Officer) has put his skills and abilities at our disposal. End of September was a good choice, always sunny without ever sultriness, the right water temperature for wonderful baths. Happy and fun company, with Lorenzo I was able to share culinary secrets in the kitchen. With a bit of luck, we sailed for a stretch in the company of a pod of dolphins. A holiday to be repeated and recommended. Giorgia P.
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Aeolian Islands: between sea and authentic flavours

10/4/2026

Lorenzo F.

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IT

Fantastic experience discovering the Aeolian Islands. The holiday followed very natural rhythms in the name of relaxation. Our skipper Carlo was super! Always available and easy-going, with his great passion and professionalism he guided us to discover wonderful coves and islands. The group got along right away. Between the sea, laughter, aperitifs and crazy sunsets, it is a holiday that I would do again without thinking about it. Recommended!

Sailing paradise in Greece on a big 50 ft boat: the best local experience

09/29/2026

Sailor

Excellent experience, clean and efficient boat. excellent, cuisine, top quality food, nice company, owner and staff, they do this job with feeling and dedication, Too bad we didn't get to Hydra., even if it was optional, skipper prepared but a little too plastered in his role. however, experience to be redone with this team, perhaps improving my English and with a new itinerary.

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