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Sailboat yacht sailing holidays & tours in Cyclades

Discover more than 24 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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4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

2 departures available

August

€1,290

€1,190

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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4.9

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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5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

2 departures available

September

€1,000

Per person

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4.9

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

July - September

Starting from

€1,080

Per person

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4.9

Super!

Paros Serifos Kytnos the fantastic Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August

€950

Per person

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4.9

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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5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

Per person

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4.9

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!

7 giorni a vela alle Cicladi con gran finale a Santorini

Greece: Cyclades

6 days - 7 nights

One departure available

August - September

€1,025

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,160

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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Reviews - Sailboat yacht sailing holidays & tours in Cyclades

394 reviews

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From Mykonos to Milos

07/2/2026

Maximiliano S.

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AR

Great experience, we traveled 2 couples and we are very grateful for all the attention provided by Andrea, we sailed through all the cyclades and she made us enjoy and share great moments and know places. Unique and incredible and having fun with our travel companions Elena, Patrick and Toni, who were very funny. A sublime experience.

In the heart of the Cyclades, from Milos to Athens (Lavrio)

07/2/2026

Christine H.

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DE

This was my first sailing trip and I was able to have an exciting and valuable experience. Unfortunately, we could not follow the originally planned route due to the weather. But Andrea quickly had an alternative ready. Unfortunately, the weather conditions were sometimes challenging for me despite the changed route. But Andrea led us confidently through them and I guided myself safely at all times. Whenever possible, Andrea responded to our wishes, and he also contributed many of his own suggestions and ideas, which certainly simplified the decision-making process within our group. At the same time, I would have liked to see more proactive communication regarding the respective daily schedules. The boat has already been allowed to cover many nautical miles, which can be seen in one place or another. But everything you need is available. For me as a sailing novice, the distances covered could have been a little shorter and the rest periods more extended. But this was certainly also due to the changed, longer route. Thank you Andrea for this experience and your support! 😌

From Piraeus to Mykonos: the Aegean by sail, with skipper and on-board kitchen

06/24/2026

Cesare S.

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IT

Annalisa and Emanuel were fantastic hosts! They made us sail and cooked us excellent meals making us spend a beautiful week discovering the sea of the Cyclades and its beautiful bays, despite the Meltemi
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In the heart of the Cyclades, from Milos to Athens (Lavrio)

06/24/2026

Alessandro A.

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IT

Spectacular experience. Beautiful landscapes, meetings with spectacular people, good food. Unfortunately, due to Meltemi at winds and more knots every day, the route has been changed to avoid sailing against the wind every day, but you must always keep in mind that it can happen and that you have to adapt to the sea and the wind. Andrea Exceptional skipper, he made us feel safe throughout the trip, solved every problem that arose, suggested the best solutions to navigation problems, as well as being infinitely available to the needs of the guests.

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