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Private yacht sailing holidays with skipper in the Cyclades

Visiting the Cyclades islands by hiring a sailboat will be one of the most beautiful experiences you can do. Choose between sailing, catamaran and gulet and let yourself be conquered by the contrast of the blue and white of Mykonos, Santorini, Paros and the Little Cyclades.

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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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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!

Luxury catamaran cruise in the Cyclades

Greece: Cyclades

7 days - 7 nights

7 departures available

August - November

Starting from

€1,000

Per person

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5.0

New

Milos, Folegandros and the fantastic Southern Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

July

€1,050

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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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

One departure available

September

€1,080

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

€1,090

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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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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Reviews - Private yacht sailing holidays with skipper in the Cyclades

85 reviews

The most spectacular islands of the Cyclades: from Athens to Milos

07/13/2026

Marcella F.

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IT

It was a beautiful holiday! The places visited and the sea were simply stunning. The boat was beautiful, comfortable and equipped with everything you need to spend a week relaxing. A special thanks to Alessio, our skipper: an attentive, kind person and always available to meet our requests, helping to make the experience even more enjoyable. An experience I highly recommend!
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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.

-

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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