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.
BEST PRICE GUARANTEE
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.
Sailing holidays in the Balearic Islands with a local skipper
Sailing holidays in Croatia with a local skipper
Sailing holidays in Corsica with a local skipper
Sailing holidays in Greece with a local skipper
Sailing courses & regatta with professional skipper
Sailing holidays in Aeolian Islands with a local skipper
Why you should book a holiday with Sailsquare?
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!
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