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Offshore yacht sailing holidays & tours in Cyclades

Discover more than 1 opportunities to get on board a Offshore adventure in Cyclades. A unique experience with a local skipper, starting at €350 a week.

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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

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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 - Offshore yacht sailing holidays & tours in Cyclades

36 reviews

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From Kos to SANTORINI and IOS to discover all the Cyclades with a luxury boat - hostess/chef on board

09/3/2023

Antonio M.

Unique experience, with two professionals of the sea. The sailing holiday always reserves many adventures and unlike many other experiences it relies heavily on the sensitivity of the skipper to define the daily program based on the weather forecast. Renato, with his vast experience, managed to bring out the best out of the week, making us explore extraordinarily beautiful places. Lulú seasoned everything with style and attention to detail, delighting us with his excellent cuisine. The boat is gorgeous, spotless and reliable! Highly recommended.
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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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We cross the Aegean from Athens to Mikonos and Kos: the most beautiful Cyclades - Hostess Chef on board

08/4/2023

Frédéric B.

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Switzerland

++wild bays visited ++food on the boat boat ++beautiful, ++maintained and ++comfortable +treated like private guests -not like paying customers -every act (wake up, breakfast, swimming, changing back to dry clothes, smoking..) was strictly timed. Without ANY obvious reason (plenty of time to sail to the next point) -6 sailing days booked. In total only 3 hours on sail, the rest on motor (no wind when we were out) & 2 days spent in harbors because the wind could be too strong. No effort made when noticed that we could have have (sportively) sailed. Frustrating to see sailing boats offshore while being on a beach/village -communication rather existent. When R. feels challenged by a question, he overreacts (Ex: by leaving the commands of the boat to us because we dared to ask if we could use sails instead of motor OR by calling us "new rich people" when we asked for the final count for the EUR 400 pp for the current expenses.) -age 48?!? -no instruction -feeling to be at the wrong place -------- SKIPPER ANSWER ------------- Dear Frederic, We are sorry that your first boat experience did not meet your expectations. On the boat there are rules to be respected regarding smoking (unthinkable to smoke while sailing and in the cabin!), order and cleanliness so that everyone is comfortable. The itinerary you have chosen (From Athens to Kos) is an adventurous choice for those who love to travel many miles. Unfortunately the wind cannot be booked and when it is too strong for safety reasons we stop. Sailing cannot be learned in a week and neither can education. Leave the cabin in the shameful condition in which you left it (literally throw away sheets) and then ask for the final report, which, as you were told, can be consulted at any time and available to everyone (with receipts and invoices) on the table from correspondence, two days after finishing the cruise, it is incomprehensible. It was not a pleasant experience for us.
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From Milos to Athens ... an Aegean to be traced

07/23/2023

violaine l.

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France

We (parents and our 6 children from 8 to 17 years old) came back excited from our cruise in the Cyclades with Alessandro. Beautiful sailings despite a powerful wind! He knew how to keep us serene and make us discover very beautiful places always in joy and good humor. We warmly recommend!

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