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Sport & wellness yacht sailing holidays & tours in Greece

Discover more than 3 opportunities to get on board a Sport & wellness adventure in Greece. A unique experience with a local skipper, starting at €350 a week.

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 - Sport & wellness yacht sailing holidays & tours in Greece

125 reviews

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Sailing holiday with yoga and SUP in the Saronic islands

08/20/2025

madelaine w.

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United Kingdom

What a fabulous trip! Everything I'd hoped for and more. A great mix of relaxation and adventure with fabulous company. It was great to learn a bit about sailing whilst exploring some beautiful islands.
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Sailing and Hiking in the Cyclades

07/14/2025

Marco P.

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Italy

We had a very nice holiday!
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Sailing WellEssere in Ionian Greece

09/14/2024

Barbara P.

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Italy

Wonderful trip to the Ionian islands, sailing in the crystal clear sea in complete relaxation, between swimming, snorkeling, his and visiting the most characteristic islands. Lo skipper Fabrizio, his wife Sari, with the cat Kekku, welcoming and helpful, deeply love these islands and took us to the most beautiful bays, where we woke up in silence; we happened to be accompanied by a turtle or to try a reiki treatment with Fabrizio. The boat is cared for in every detail and very comfortable. Sari's vegetarian cuisine is delicious. Highly recommended!
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Esplorare ciò che è nascosto nelle Piccole Cicladi

10/17/2023

Carlo D.

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Italy

I didn't do the review before for lack of time and desire given how it went. I don't know how the others managed to write the previous reviews... the fantastic places an infinite peace, but I would have some things to say about it, the boat was old '89 and badly put you could not even shower inside and only cold water outside with shower. (Water run out 2 days before returning due to problems with the tanks according to Gianluca) In addition, the rigging and condition of the boat and sails were at risk (heard in a low voice even from him to the other crew member). The cockpit, small invisible table, you didn't even fit in there for lunch. The skipper was not very sociable, sometimes grumpy, he did not know the areas where we were sailing, so we sailed only during the day, taking time away from all the activities we could do, different places to see. I'm not a pain in the ass, I just have a bit of experience at sea and sailing

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