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Sailboat yacht sailing holidays & tours in Cyclades

Discover more than 27 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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4.8

Super!

Athens to Paros: the best of the Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August - September

€950

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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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

7 departures available

June - October

Starting from

€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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4.8

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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5.0

Super!

Sailing Odyssey in the heart of Cyclades

Greece: Cyclades

6 days - 6 nights

One departure available

September

€1,100

€990

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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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 - Sailboat yacht sailing holidays & tours in Cyclades

390 reviews

Sailing in the Aegean, the sea of the Gods!

06/1/2026

Viviana C.

A tour full of adventure! Andrea is very professional and with his experience he made us discover these wonderful islands, in all their beauty.

Sailing in the Aegean, the sea of the Gods!

05/31/2026

James W.

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IT

Everything about this experience was 5 star! Andrea is an incredible professional who knows how to curate the perfect tour. If given the chance, we would absolutely sail with him again!
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Sailing in the Aegean, the sea of the Gods!

05/25/2026

Massimo O.

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IT

Andrea is exquisite and knows how to put you at ease. He is prepared and able to solve the various unforeseen events typical of life at sea. The variable weather prevented us from making the most of the experience at sea but the alternative proposals for shore excursions proposed by Andrea were equally exhaustive.
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Sailing in the Cyclades

04/22/2026

Miguel M.

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ES

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.

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