Private yacht sailing holidays with skipper in the Cyclades
Visiting the Cyclades islands by hiring a sailboat will be one of the most beautiful experiences you can do. Choose between sailing, catamaran and gulet and let yourself be conquered by the contrast of the blue and white of Mykonos, Santorini, Paros and the Little Cyclades.
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Get onboard solo, with your family or your friends
Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.
Find out before you book who's waiting for you on board
Find out more about the skipper and travellers who have already booked the holiday, to find out more about the
Sailing holidays that suit all budgets
On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.
Reviews - Private yacht sailing holidays with skipper in the Cyclades
76 reviews
Sailing in the Cyclades
10/12/2025
Lisa B.
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Germany
Milos to Paros: the best of the Cyclades
09/27/2025
Rocco G.
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Switzerland
From Paros to Milos, the hidden gems of Cyclades
09/24/2025
Anna B.
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Germany
Milos to Paros: the best of the Cyclades
09/23/2025
Massimiliano B.
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Italy
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