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Catamaran yacht sailing holidays & tours in the Cyclades

Enjoy the cool wind and warm sun of the Cyclades on board a comfortable a comfortable catamaran. Embedded in the turquoise waters of the Aegean Sea discover the large and small Cyclades with their white houses and windmills trying to trap the Meltemi wind.

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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 - Catamaran yacht sailing holidays & tours in the Cyclades

28 reviews

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Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

08/25/2024

Rolf S.

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Switzerland

It was all great Personally, I would have liked to sail even more....
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Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

07/28/2024

Nino C.

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Italy

Beautiful experience! Aga and Greg are two amazing people and made our week a delight. Aga prepares excellent breakfasts based on fruit and yogurt and light lunches with typical Greek products, often homemade by their friends. Greg is an amazing captain who steers his [hidden] Cat to perfection, making you feel safe at all times in all wind conditions and allowing you to enjoy your holiday even when you find a meltemi at 40 knots like we had the first 3 days. While the other boats were in port, we always went out as if nothing had happened....thanks Greg!! Honorable mention also for Stark, the third member of the crew. Always discreet person, but super nice when involved! Keep up the good work and we will surely be back on board with you, maybe as early as next winter in the Bahamas... 😉
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LAST MINUTE mini cruise from Amorgos to Astipalea

08/28/2023

Luca T.

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Switzerland

Fulvio, an experienced captain, embodies the essence of Italian maritime expertise, infusing his vast knowledge and genuine passion for the sea into his teachings. Under his guidance, we embarked on secure and serene voyages to offbeat destinations, seamlessly blending the beauty of the sea with enriching cultural immersions and unforgettable excursions. This voyage was not only a nautical adventure but also a celebration of the great Italian vibe.
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Navigation in the mythical Cyclades Islands Kea, Kithnos, Syros, Serifos

08/11/2023

Emiliano r.

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Italy

I'll be short of it: This is not the first experience on a sailing boat. The islands Kea and Kithnos are very beautiful, the catamaran is well maintained even though it is more than 20 years old. with the rest of the group I had a great time, his wife Elisa is a very delicious sensitive woman, she is very good at cooking. the SKIPPER is an inhospitable person. He was always yelling with his wife, when he anchored the anchor in the sea, even when he raised the sail he was always making a mess and screaming, my feeling is that he was very anxious.... Ultimately! don't ever go on a vacation again with a screaming SKIPPER makes cain is anxious.....

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