Sailing cruise in the Mediterranean with skipper
Greece, Balearic Islands, Croatia, Italy: come aboard thousands of Mediterranean cruises. Unique experiences with a local skipper from €400 per week.
BEST PRICE GUARANTEE
If you find the same experience for a lower price elsewhere, we’ll match the price.
The magic of Mediterranean sailing cruises
Paradise islands 2 hours by plane
Aeolian Islands, Cyclades, Ionian Islands, Balearic Archipelago, Corsica and hundreds more. The Mediterranean Sea is a true paradise to explore by sailboat. Discover places only accessible by boat, learn to sail and come back to land with memories full of them.
Original family holidays
The Mediterranean is probably the best destination for a first cruise on a sailing boat or catamaran. Are you looking for an original formula for your next family holiday? Your children will be delighted to live outside and in the middle of nature for a week.
Rent a whole sailboat for more freedom
Hiring a boat with a skipper is the best way to enjoy these beautiful places in complete freedom. With family or friends, you can sail at your own pace by setting your own schedule with the skipper.
Sailing holidays in the Balearic Islands with a local skipper
Sailing holidays in Croatia with a local skipper
Sailing cruise in Corsica with 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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