Private yacht sailing holidays with skipper in the Cyclades

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.

FLEXIBLE CANCELLATION.

Stress-free booking: you can cancel up to 24 hours before departure!

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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!

Reviews - Private yacht sailing holidays with skipper in the Cyclades

2 reviews
20 / 10
Nurit R.

Nurit R.

review about Walking around the Cyclades - Exclusive boat June 2022

10 / 10
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!
Patrick P.

Patrick P.

review about ALL INCLUSIVE crewed sailing holidays between Nafplion & Poros, both near Athens July 2019

10 / 10
An extraordinary week sailing with Christopher and Marie Nice welcome extra swimming course in beautiful coves Good music in the evening and delicious meal What a good time Adam and Allan took their first sailing course with Captain Christopher Do not hesitate to embark Thank you a thousand times Adam Allan Zena and Patrick
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