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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

Premium

Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

Greece: Cyclades

6 days - 7 nights

One departure available

August

€2,947

€2,800

Per person

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5.0

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

7 departures available

August - October

Starting from

€1,080

Per person

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4.9

Super!

Fast cruising Cicladi Occidentali

Greece: Cyclades

6 days - 7 nights

One departure available

August - September

€955

Per person

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4.9

Super!

Milos, Kimolos, Poliegos, Folegandros, the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€870

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

2 departures available

August - September

Starting from

€955

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board from Santorini to Kos

Greece: Cyclades

7 days - 6 nights

One departure available

September

€1,050

Per person

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4.9

Super!

Astypalaia, Anafi and Santorini: the pearls of the Southern Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August

€990

Per person

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4.9

Super!

From Paros to Mykonos

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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4.9

Super!

Mykonos to Athens by Fast Cruise

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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4.9

Super!

Paros, Serifos, Kytnos, the fantastic Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€790

€711

Per person

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5.0

Super!

We will depart from Kos to head to Mykonos with a very comfortable boat

Greece: Cyclades

7 days - 6 nights

One departure available

September

€750

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

September

€800

Per person

Why book a holiday with Sailsquare?

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The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

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.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

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 - Private yacht sailing holidays with skipper in the Cyclades

44 reviews

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We cross the Aegean: Milos, Small Cyclades, Amorgos, Astypalea

06/19/2025

Elisa L.

-

United Kingdom

The trip was great. Andrea is a very experienced skipper and knows all hidden gems of Greece! Every day was full of surprises, including seeing turtles, tuna fishing, and local wine festival. I particularly appreciated Andrea’s attention to the environment and the promotion of a responsible, local and more authentic way of travelling. Highly recommended!
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Fast sailing holiday in the Cyclades with gourmet cuisine on board

06/15/2025

Alberto L.

-

Italy

Un Sogno a Vela Indimenticabile con Lorenzo e Annalisa Se cercate un'esperienza in barca a vela perfetta tra le Cicladi, scegliete Lorenzo e Annalisa. Per una settimana, ci hanno guidato da Lavrio a Mykonos, esplorando le Piccole Cicladi, e siamo rimasti entusiasti. La loro conoscenza delle isole è eccezionale, permettendoci di scoprire angoli di paradiso e condizioni di navigazione ideali. A bordo, l'atmosfera è sempre stata rilassata e accogliente. Da segnalare la cucina veramente deliziosa e variegata!! . La loro sinergia crea un ambiente sereno e piacevole. Le Piccole Cicladi ci hanno regalato paesaggi mozzafiato, e grazie a loro abbiamo vissuto appieno ogni momento: bagni in baie deserte e cene in taverne tipiche. Lorenzo e Annalisa sono compagni di viaggio appassionati ed esperti. Hanno superato ogni aspettativa, trasformando una vacanza in un'avventura straordinaria. Li raccomandiamo vivamente a chiunque desideri un'esperienza autentica e indimenticabile tra le isole greche.
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Cyclades and Microcyclades with a magnificent 15-meter boat

06/15/2025

Ester L.

-

Italy

La nostra esperienza in barca con Fabio è stata straordinaria! Nonostante fosse la nostra prima volta in barca a vela ci siamo sentiti subito a casa e a nostro agio. La barca è accogliente ed ha tutti i comfort, e i pasti che abbiamo fatto a bordo hanno avuto i panorami più belli e irripetibili che si possano immaginare. Fabio ci ha insegnato e raccontato molto della vita in mare, ed è stato per noi un arricchimento e un'ispirazione per ripetere questa bellissima esperienza anche in futuro. I luoghi che abbiamo visto sono incantevoli, inoltre Fabio li conosce tutti molto bene e ci ha fatto da guida (anche gastronomica!). Non potremmo consigliare esperienza migliore! Sarà bellissimo anche per neofiti!!
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Sail from Milos to Mykonos with a Beneteau 50 experience the Cyclades

06/7/2025

Denis P.

-

Italy

Splendida settimana tra le Cicladi… Gianfranco é davvero un grande capitano, che oltre alle doti nautiche sa anche coinvolgerti nella navigazione e farti sentire subito a tuo agio a bordo… La barca poi… Splendida! L’unico problema é il dover sbarcare al termine della vacanza… Grazie Gianfranco!

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