Sailing holidays in the Cyclades with a local skipper
Discover the treasures of the Aegean Sea - a collection of islands with their own unique charm, landscapes, and coastlines. The Cycladic Islands act as a brilliant destination to unwind, relax, and connect with some of the most stunning natural beauty. Explore the stunning Santorini, Mykonos, and Ios with a passionate, local skipper.
If you find the same experience for a lower price elsewhere, we’ll match the price.
Why you should book a holiday with Sailsquare?
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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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