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Sailboat yacht sailing holidays & tours in Cyclades

Discover more than 31 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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4.9

Super!

Fast cruising Cicladi Occidentali

Greece: Cyclades

6 days - 7 nights

One departure available

August - September

€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

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4.5

SHARE & SAIL - 6 days Exploring & Relaxing at the heart of Cyclades

Greece: Cyclades

6 days - 6 nights

2 departures available

October

€790

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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 - Sailboat yacht sailing holidays & tours in Cyclades

356 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

A week on a sailing boat between Santorini, Anafi, Astypalea, Nisyros and Kos – a real holiday, one of those that stay with you. Annalisa and Emmanuel, our skippers, were incredible: super prepared, but also welcoming and easy-going. They treated us like kings and queens from day one, with a care and kindness that is rarely found. Even when the wind gave us a longer stop on an island, they were able to turn everything into an opportunity to discover beautiful places, have new experiences and eat in authentic places where you spend little and really eat like a god. Even on board you can eat very well: they cook everything themselves, with fresh local products, and you can see that they put passion into it. They are not only good skippers, they are also excellent cooks! Every meal was delicious! We did everything: trekking, bathing in hot springs, visiting the caldera of a volcano, and often slept in quiet and isolated bays, under a sky full of stars. An incredible peace. We almost always sail making us participate in the maneuvers and explain everything to us with patience and passion. It's not your average all-inclusive holiday, it's a different, more authentic and free experience – and that's why it's special. It is real sea, nature, freedom, simplicity. If you are looking for something authentic, away from the chaos and full of beauty, I highly recommend it.
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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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