Mediterranean sailing holidays

Mediterranean sailing holidays

Discover thousands of sailing holidays in the Mediterranean. Book a spot onboard and live a unique experience with a local skipper. Starting at €400 a week.


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

The magic of sailing holidays across the Mediterranean

Paradisiacal islands on your doorstep

The Amalfi Coast, Aeolian islands, Cyclades, Ionian islands, Dodecanese, Balearic archipelago, Corsica and hundreds of others. The Mediterranean Sea brings together some of the world’s most outstanding sailing destinations. Learn how to sail, or sharpen your skills with sailing course experiences and regattas!

An original holiday with your family

The Mediterranean is perhaps one of the best destinations for a first sailing cruise, whether that is solo, as a couple, with friends or as a family. Looking for an original way to holiday? Look no further.

Rent a whole sailboat or catamaran for maximum freedom

Booking a whole boat with a skipper is the best way to enjoy the beautiful destinations of the Mediterannean. By renting a whole boat, you can sail with your friends or family at your own pace and customise your own itinerary with your skipper.

Why you should book a holiday with Sailsquare?

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The leading sailing holiday marketplace

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!

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