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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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Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

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 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

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

2 reviews

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Walking around the Cyclades - Exclusive boat

08/2/2022

Nurit R.

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United States

We had the most amazing family vacation around the Cyclades islands with Max and Cori this summer. Knowledgeable and accommodating at all times, they made our week with them the best and most memorable ever. They know the best islands, local tavernas, beautiful private beaches and coves. They even taught my husband how to sail and allowed me and my daughter to take the wheel. The whole week we spent with them was unforgettable, the food delicious and we can’t wait to do it again!
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Sailboat holidays from Paros to discover the minor Cyclades

08/5/2019

Patrick P.

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France

Une semaine extraordinaire en voilier avec Christopher et Marie Accueil sympa parcours extra baignade dans de superbes criques Bonne musique le soir et repas délicieux Que du bon temps Adam et Allan pris leur premier cours de navigation avec le captain Christopher N’hésitez pas à embarquer Merci mille fois Adam Allan Zena et Patrick

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