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Offshore yacht sailing holidays & tours in Cyclades

Discover more than 2 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.

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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


Antonio M.

Esperienza unica, con due professionisti del mare. La vacanza a vela riserva sempre tante avventure e a differenza di tante altre esperienze si basa molto sulla sensibilità dello skipper a definire il programma giornaliero sulla base delle previsioni meteo. Renato, con la sua vastissima esperienza, è riuscito a tirare fuori il meglio dalla settimana, facendoci esplorare posti straordinariamente belli. Lulú ha condito il tutto con lo stile e la cura dei dettagli, deliziandoci con la sua ottima cucina. La barca è stupenda, pulitissima e affidabile! Consigliatissimi.
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LAST MINUTE mini cruise from Amorgos to Astipalea


Luca T.



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


Frédéric B.



++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


violaine l.

Nous (parents et nos 6 enfants de 8 à 17 ans) sommes revenus emballés de notre croisière dans les cyclades avec Alessandro. Belles navigations malgré un vent puissant ! Il a su nous garder sereins et nous faire découvrir de très beaux endroits toujours dans la joie et la bonne humeur. Nous recommandons chaleureusement !

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