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Sailboat yacht sailing holidays & tours in Cyclades

Discover more than 39 opportunities to get on board a Sailboat adventure in Cyclades. A unique experience with a local skipper, starting at €350 a week.

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4.8

Super!

Ios, Sikinos, Folegandros and Anafi: the fantastic Cyclades of the South

Greece: Cyclades

7 days - 7 nights

2 departures available

August

€990

Per person

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4.9

Super!

Fast Sailing Experience between Authentic Islands and Good Food

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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4.8

Super!

From Milos to Athens: the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€750

Per person

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4.8

Super!

Paros Serifos Kytnos the fantastic Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August

€950

Per person

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4.8

Super!

Route to the South: The Small Cyclades and spectacular Santorini

Greece: Cyclades

7 days - 7 nights

One departure available

September

€850

€765

Per person

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5.0

Super!

Sailing in the Aegean, the sea of the Gods!

Greece: Cyclades

7 days - 7 nights

One departure available

May

€500

Per person

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4.8

Super!

From Ios to Milos, the best of the Central Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€750

Per person

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4.9

Super!

Cyclades from Paros to Milos on magnificent 15-meter boat

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

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4.8

Super!

Milos to Paros: the best of the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

July - August

€900

Per person

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4.9

Super!

Baie and fast sailing from Milos to Paros

Greece: Cyclades

6 days - 7 nights

One departure available

September

€890

Per person

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4.8

Super!

From Kalamata to Milos: the fantastic and wild South Peloponnese

Greece: Cyclades

7 days - 7 nights

One departure available

July

€900

Per person

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4.8

Super!

Athens to Paros: the best of the Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August - September

€950

€903

Per person

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Reviews - Sailboat yacht sailing holidays & tours in Cyclades

387 reviews

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Sailing in the Cyclades

04/22/2026

Miguel M.

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Spain

Exceptional experience!! Yann is a skipper who knows the navigation area and the most suitable anchorages and ports well. In addition to being an excellent sailor, he is an endearing person who seeks the well-being of his "crew", carrying out activities on land such as hikes or visits to interesting places that give added value. His boat "[hidden]" is a sailboat of the highest level, very comfortable and designed to sail in extreme conditions and therefore absolutely safe. Yann keeps it in pristine condition and is spotlessly clean. In short, it is a highly recommended experience.

CYCLADIC ESCAPE - Active Holidays: 5 days Sailing & Exploring Unknown Greece  

10/18/2025

Tina F.

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Germany

I very much liked the Mixture of sailing, stops for swimming, attractions and good food in the Taverns. The boat was very comfortable and well-equiped. Orestis Was very friendly, Attentive and professional. It was perfect and I would love to do another Trip in future.

Sailing in the Cyclades

10/12/2025

Lisa B.

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Germany

Yann has a great and modern boat and always surprised us with culinary delights - whether on board or ashore. The excursions and activities were very varied and we enjoyed the tavern visits very much. Linguistically, it was not always easy for us in the group, as almost all the others in the group, like Yann, were native speakers of French or knew the language and then often switched to French in group situations with each other, where we felt left out and often had the feeling that we didn't notice the plans. That was a bit of a shame. Yann is an experienced skipper, we always felt safe - he knows the Cyclades very well and we were able to explore great bays and places. However, we caught a week with quite strong winds, which brought us as beginners to some limits (seasick) - we personally would not have had the ambition to cover such long distances under these circumstances. All in all, we had an intense adventure, which we remember with many highlights. :) thank you

Milos to Paros: the best of the Cyclades

09/27/2025

Rocco G.

-

Switzerland

Alessandro is a legend, an excellent cook and tries to fulfill customer requests in the best way always taking into consideration the safety and comfort of the crew. You feel like you care about delivering the best experience possible. We had bad luck with the weather, but despite this it was an adventurous and nice week.

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