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Sailboat yacht sailing holidays & tours in Greece

Discover more than 12 opportunities to get on board a Sailboat adventure in Greece. A unique experience with a local skipper, starting at €350 a week.

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4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

21 departures available

May - October

Starting from

€1,000

€950

Per person

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4.9

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

26 departures available

March - September

Starting from

€650

€618

Per person

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4.9

Super!

Cyclades and Microcyclades with a magnificent 15-meter boat

Greece: Cyclades

7 days - 7 nights

3 departures available

May - June

Starting from

€750

Per person

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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

33 departures available

March - November

Starting from

€460

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

33 departures available

March - October

Starting from

€460

Per person

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Sailing in the Saronic Archipelago

Greece: Saronic Islands and Athens area

6 days - 7 nights

2 departures available

October - November

€700

Per person

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4.0

Sailing the Small Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

October

€789

Per person

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4.3

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

17 departures available

May - October

Starting from

€845

Per person - min 2 pax

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4.5

SHARE & SAIL - 5 days Exploring & Relaxing at the heart of Cyclades

Greece: Cyclades

5 days - 5 nights

3 departures available

May - October

€880

Per person

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5.0

Ionian Islands by Sailing: Trekking, Snorkeling and Sea Adventure

Greece: Ionian Islands

6 days - 6 nights

2 departures available

October

€600

Per person

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4.8

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

16 departures available

June - September

Starting from

€600

€540

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

April - May

€990

Per person

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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 Greece

1762 reviews

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Sailing in the Cyclades

10/12/2025

Lisa B.

-

Germany

Yann has a great and modern boat and always surprised us with culinary delights - whether on board or ashore. The excursions and activities were very varied and we enjoyed the tavern visits very much. Linguistically, it was not always easy for us in the group, as almost all the others in the group, like Yann, were native speakers of French or knew the language and then often switched to French in group situations with each other, where we felt left out and often had the feeling that we didn't notice the plans. That was a bit of a shame. Yann is an experienced skipper, we always felt safe - he knows the Cyclades very well and we were able to explore great bays and places. However, we caught a week with quite strong winds, which brought us as beginners to some limits (seasick) - we personally would not have had the ambition to cover such long distances under these circumstances. All in all, we had an intense adventure, which we remember with many highlights. :) thank you
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

10/7/2025

Sharron G.

-

United Kingdom

We were the last group to sail this year & enjoyed reading the other reviews as everyone had such positive feedback. We weren’t disappointed and although the weather wasn’t kind to us we couldn’t have had a better experience. Alessandro is an amazing skipper, he’s young but he’s been sailing forever & certainly knows his way around his boat and the waters & islands we sailed around. He made you feel safe & well looked after. Carlo couldn’t do enough for us all & his food & hospitality were excellent, making us laugh as we tried to speak Italian. We couldn’t believe how he was able to serve up the dishes from the tiny galley kitchen. Something different every day and he even caught a tuna & that was served up for lunch, you don’t get fresher than that. We couldn’t have had a better adventure with better crew. Thank you Alessandro & Carlo! PO5 will return xxxxx
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

10/6/2025

Corinne W.

-

Switzerland

It was very nice and beautyful, when the sun was shining.☀️We had a good time and the crew was very nice, helpful. And kind. Thank you!
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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!

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