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Yacht sailing holidays & skippered tours in Greece

Discover more than 3 sailing holidays in Greece. Book a spot onboard and live 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 - Yacht sailing holidays & skippered tours in Greece

1896 reviews

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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

10/1/2025

Arina R.

-

Spain

It was an unforgettable journey 🤩 I totally recommend it to everyone. Andrea is very professional skipper with a lot of experience, he takes care about safety of the guests and carefully plan the route. And the most important he is an awesome person to have great conversation with. We learned so much about the sailing during the week. The hostess Marta is very kind and cooks delicious lunch. It was so comfortable that we don’t have to worry about what to eat for the breakfast or the lunch, everything was prepared by her. We visited incredible bays, had so much swim and slept under the stars sky in the sea, nothing else to ask for. But the special mentioning is to their dog Matthias, real marine dog who stole our hearts ❤️ During raining winter days I will think about Matthias that he is sailing somewhere in the Mediterranean Sea and smile! We will be missing this week, but for sure one day we will come back!
avatar image

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

10/1/2025

Arina R.

-

Spain

It was an unforgettable journey 🤩 I totally recommend it to everyone. Andrea is very professional skipper with a lot of experience, he takes care about safety of the guests and carefully plan the route. And the most important he is an awesome person to have great conversation with. We learned so much about the sailing during the week. The hostess Marta is very kind and cooks delicious lunch. It was so comfortable that we don’t have to worry about what to eat for the breakfast or the lunch, everything was prepared by her. We visited incredible bays, had so much swim and slept under the stars sky in the sea, nothing else to ask for. But the special mentioning is to their dog Matthias, real marine dog who stole our hearts ❤️ During raining winter days I will think about Matthias that he is sailing somewhere in the Mediterranean Sea and smile! We will be missing this week, but for sure one day we will come back!
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Sailing paradise in Greece on a big 50 ft boat: the best local experience

09/29/2025

Wouter d.

-

Netherlands

Nice trip
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

09/29/2025

Sirma I.

-

Bulgaria

It was a great experience. I am still excited, but also very relaxed by this amazing week on water with Andrea and Marta! They are so kind and attentive. All wishes are considered. It is not only a yacht trip. It is a whole program with daily tours visiting small bays, islands and ports. The recommendations we got were just right - for restaurants, for sights, for all the interesting places. The knowledge and experience of the crew is great. We had such a great time and we can’t wait for the next summer to come back and bring more friends with us. Ah yes! The lovely Mattias, forever in our hearts!

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