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Sailboat yacht sailing holidays & tours in Greece

Discover more than 25 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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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

5 departures available

September - November

Starting from

€550

Per person

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5.0

Super!

Sailing in the eastern Aegean, between the Dodecanese and the Cyclades!

Greece: Dodecanese

8 days - 8 nights

One departure available

September

€650

Per person

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4.8

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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4.8

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

€750

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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4.8

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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4.8

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

6 departures available

September - October

Starting from

€1,100

€880

Per person

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5.0

Super!

From Paros to Milos, the hidden gems of Cyclades

Greece: Cyclades

5 days - 5 nights

One departure available

September

€900

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

One departure available

October

€550

Per person

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5.0

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

September - October

€1,080

Per person

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5.0

Super!

Corfù Paxos Antipaxos

Greece: Ionian Islands

6 days - 6 nights

One departure available

September

€900

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board - Rhodes to Kos

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

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 Greece

1737 reviews

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

09/13/2025

Stefano S.

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Italy

An unforgettable experience from start to finish, and I can’t recommend it enough! First of all, our skipper Arnon was absolutely fantastic. Calm, professional, and with a great sense of humor, he made everyone feel safe and relaxed from the moment we stepped on board. His deep knowledge of the area meant that every stop was better than the last. He also involved us in the sailing, which made the experience even more fun! A huge shoutout as well to our wonderful hostess, Agatka. Her cooking was simply incredible — every meal was fresh, flavorful, and beautifully presented. She had an amazing way of making the boat feel like home, always with a smile, and was invaluable in organizing our land expeditions. You can tell she really loves what she does, and it shows in every detail. The itinerary was perfectly paced — a mix of sailing, swimming, exploring on land, and many nice little seaside restaurants. I left the boat with new friends, a camera full of memories, and a heart full of gratitude. If you’re considering this trip — go for it. You won’t regret it.
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

09/13/2025

Jacobus Daniel v.

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New Zealand

We had a blast! Food was great - the skipper was awesome, he really went out of his way to show us the best local spots and make the experience great. Would definitely highly recommend. Thank you so much for a great time!
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Come and discover the Saronic Islands from Poros

09/12/2025

Floor v.

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Netherlands

We would like to write an amazing, 100% recomommandation review for Patrick and Sabine. It was really the best trip we've been on. They are so welcoming on board, making you feel at home right away. They not only take you to really nice places, they share their home and all the comes with it on the boat. They are considerate in your wishes, interested, caring and Sabine is and absolute amazing chef! If you want to relaxe, explore, chat with them, have a drink or just don't do anything, they really accomodate you in your wishes. All is fine, and that's what made them amazing hosts for us. We would really love to see them again and take a trip with them again!
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Sailing in the Cyclades

09/9/2025

Jana H.

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Germany

Our very first sailing trip turned out to be an unforgettable great experience! Great boat, interesting excursions, delicious food, and most importantly with skipper Yann the dearest and most caring person you could wish for! We like to remember all the experiences (including the card games that were new to us) and all your unexpected surprises on a boat. A big thank you (unfortunately without blue flip-flops 😉) Jana and Flo

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