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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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4.7

Luxury catamaran cruise in the Cyclades

Greece: Cyclades

7 days - 7 nights

4 departures available

September - November

€1,000

Per person

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4.9

Super!

Cyclades from Milos to Milos

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

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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

€760

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

Starting from

€1,000

€800

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

€790

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

€940

Per person

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4.9

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

October

Starting from

€950

Per person

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4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,290

€1,161

Per person

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5.0

Sailing Odyssey in the heart of Cyclades

Greece: Cyclades

6 days - 6 nights

One departure available

September

€990

Per person

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4.0

Sailing & Diving in the Small Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,390

€1,251

Per person

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4.6

Cabin boarding in the Cyclades, Astypalea and Santorini, sailing 17m. with chef

Greece: Cyclades

7 days - 7 nights

One departure available

August - September

€1,400

Per person

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5.0

Exclusive boat, you choose the route and the Cyclades islands to see!

Greece: Cyclades

7 days - 7 nights

One departure available

September

€917

Per person

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Reviews - Private yacht sailing holidays with skipper in the Cyclades

95 reviews

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Ios, Santorini, Anafi: the breath of the Cyclades

08/26/2026

Chiara Q.

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IT

Alessio is a very prepared, kind and helpful skipper. Wonderful and very comfortable boat, and the sea-islands of the Cyclades are a real enchantment! Beautiful experience, I recommend!
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Luxury catamaran cruise in the Cyclades

08/18/2026

Paolo F.

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CH

The holiday was made in the Saronics, due to the adverse weather in the Cyclades. It was a good choice since friends later told me that they had had a very bad week because of the wind on those islands. Hydra and Spetses are real gems. Bertrand is very helpful, he accompanied us with the tender even at inconvenient times and always put our safety first. The boat is very comfortable and new, even in 10 you have all the comforts and space you need.

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

08/13/2026

Aurora G.

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IT

It was the first experience on a boat... unique and spectacular! Annalisa and Emanuel were able to make us feel immediately at ease. Both, experienced and close-knit sailors, emanate an immense passion for what they do, able to transmit it to all their companions. Two sunny, kind, helpful and knowledgeable people who take you to discover fantastic and exclusive places; deserted beaches and islands, far from the chaos, where it is possible to admire all the beauty of the Greek islands both during the day and during the night with breathtaking starry skies. The boat is well organized, allowing you to move freely and safely even in small spaces. Moreover, Annalisa and Emanuel are also fantastic cooks, capable of preparing exquisite delicacies with local flavors and in great abundance! Also thanks to our travel companions, we can say that we embarked as perfect strangers and then disembarked feeling part of a group of friends. Thank you very much Emanuel and Annalisa for this unforgettable experience... See you soon!
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From Milos to Mykonos by sail, with skipper and on-board kitchen

08/11/2026

Anna M.

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IT

First experience on a sailing boat, it far exceeded my expectations! Emanuel & Annalisa are fantastic: they steer the boat with great safety, even when the weather conditions are not always easy due to the Meltemi and they know how to find sheltered bays where they can enjoy the wonderful Greek sea and breathtaking landscapes, far from the typical crowds of August. They cooked delicious dishes for us, making us discover and taste many local ingredients and flavors. The boat is well organized and equipped with everything you need to spend a pleasant and relaxing week. It is definitely not a holiday for everyone: it requires flexibility, a spirit of adaptation and the desire to share spaces and experiences. But once you try it, it is a type of holiday that remains in the heart. Hop on as a guest and come down as a friend! Thank you very much Annalisa & Emanuel, and fair winds!

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