Yacht sailing holidays & cruise in the Mediterranean Sea

Yacht sailing holidays & cruise in the Mediterranean Sea

Greece, Balearic Islands, Croatia, Italy: come aboard thousands of Mediterranean cruises. Unique experiences with a local skipper from €400 per week.


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

The magic of Mediterranean sailing cruises

sailing cruise in the mediterranean

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.

holiday sailboat mediterranean

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.

sailboat rental with skipper mediterranean

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.

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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