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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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4.9

Super!

Fast cruising Cicladi Occidentali

Greece: Cyclades

6 days - 7 nights

2 departures available

August - September

Starting from

€955

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!

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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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!

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!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

September

€955

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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4.9

Super!

Milos to Paros: the best of the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person

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From Paros to Milos, the hidden gems of Cyclades

Greece: Cyclades

5 days - 5 nights

2 departures available

August - September

Starting from

€900

€765

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

48 reviews

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One way from the Cyclades to the Dodecanese on a magnificent 15-meter boat

06/29/2025

Gabriele A.

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Italy

Bella esperienza in ottima compagnia. Fabio, lo skipper, un vero lupo di mare, ed Irene dolcissima presenza. Abbiamo visitato diverse isole come da programma ed oltre. Un'esperienza da rivivere, in semplicità e leggerezza, com'è stato in questa vacanza. Buon vento! Gabriele & Barbie gymnastic
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Secret Aegean with skipper and kitchen on board from Santorini to Kos

06/26/2025

Melissa C.

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Italy

Settimana in barca a vela tra Santorini, Anafi, Astypalea, Nisyros e Kos – una vacanza vera, di quelle che ti restano addosso. Annalisa ed Emmanuel, i nostri skipper, sono stati incredibili: super preparati, ma anche accoglienti e alla mano. Ci hanno trattati come re e regine fin dal primo giorno, con una cura e una gentilezza che raramente si trovano. Anche quando il vento ci ha regalato una sosta più lunga su un’isola, hanno saputo trasformare tutto in un’occasione per scoprire posti bellissimi, fare esperienze nuove e mangiare in locali autentici dove si spende poco e si mangia davvero da dio. Anche a bordo si mangia benissimo: cucinano tutto loro, con prodotti locali freschi, e si vede che ci mettono passione. Non sono solo bravi skipper, sono anche ottimi cuochi! Ogni pasto era delizioso! Abbiamo fatto di tutto: trekking, bagni nelle sorgenti calde, visita alla caldera di un vulcano, e spesso dormivamo in baie tranquille ed isolate, sotto un cielo pieno di stelle. Una pace incredibile. Si naviga quasi sempre a vela facendoci partecipare alle manovre e spiegandoci tutto con pazienza e passione. Non è la solita vacanza all-inclusive, è un’esperienza diversa, più autentica e libera – e proprio per questo è speciale. È mare vero, natura, libertà, semplicità. Se cercate qualcosa di autentico, lontano dal caos e pieno di bellezza, ve la straconsiglio.
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We cross the Aegean: Milos, Small Cyclades, Amorgos, Astypalea

06/25/2025

Anna M.

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Luxembourg

Andrea is an extremely skillful skipper, he knows exactly how to make you feel comfortable on the boat, he worries about your needs and is always ready to answer questions and curiosities. Our destinations were amazing and magic Greece just makes the rest. Highly recommended!
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Secret Aegean with skipper and kitchen on board from Santorini to Kos

06/24/2025

gina c.

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United States

The skippers are experienced sailors who care about safety + weather conditions and maintain a very clean, comfortable boat down to the smallest details. They were kind enough to help me maneuver a heavy piece of luggage which I'm super grateful for. I booked solo and extremely last minute without knowing the right questions to ask, and I do recommend conversing prior to get a feel of fit for this type of trip. I could have benefited from discussing my dietary preferences and restrictions in comparison to the group, especially given that the food is purchased and prepared by the skippers without the option of purchasing/ cooking your own. It also didn't occur to me to inquire about allotted water consumption per passenger, and in our case a swift shower wasn't possible each day whether on board or in marina. If you decide to embark, know that you are in experienced hands who will carefully anticipate weather restrictions and modify as needed, and you definitely won't be shopping or cooking. Thank you!

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