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Sailboat yacht sailing holidays & tours in Greece

Discover more than 15 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

24 departures available

May - October

Starting from

€1,200

€1,080

Per person

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4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

October - November

€585

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

34 departures available

March - October

Starting from

€460

Per person

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4.9

Super!

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

Greece: Ionian Islands

7 days - 7 nights

10 departures available

May - July

Starting from

€650

€585

Per person

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4.8

Super!

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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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

9 departures available

July - September

Starting from

€700

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

35 departures available

March - October

Starting from

€460

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

3 departures available

August

Starting from

€1,040

Per person

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Odysseus trip to Zakynthos - Kefalonia-Ithaka

Greece: Ionian Islands

7 days - 7 nights

One departure available

October

€890

Per person

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4.7

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

34 departures available

April - November

Starting from

€650

€618

Per person

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5.0

New

Corfu: sailing, dream bays and walks in the villages - hostess on board

Greece: Ionian Islands

6 days - 6 nights

2 departures available

October

Starting from

€1,200

€500

Per person

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4.9

Full sail in the blue of Ionian Greece with hostess on board

Greece: Ionian Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€870

Per person

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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

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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

2006 reviews

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The fantastic Saronic Islands and the surroundings of Athens

10/13/2026

Alexander S.

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CH

We had an exciting and memorable week on board with Alessandro. We were lucky to enjoy boat trips every day and especially loved sharing his delicious pasta meals. We quickly embraced his Italian spontaneity, with new destinations and ideas along the way, making the experience all the more adventurous and unique. A wonderful week for those who enjoy a relaxed, authentic Italian sailing experience!

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

10/12/2026

Fiona B.

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AU

Andrea was a fantastic skipper and Carol was a great hostess. The week was filled with beautiful beaches, delicious lunches and great conversations and was a perfect way to relax for a week. It was fun sailing along with the second yacht, and we had a great time playing volleyball together. The boat was comfortable and plenty of spots to relax above deck in the sunshine. I highly recommend this trip. Andrea and Alessandro are expert sailors who take the very best care of their customers and always put safety first - but maximize fun and stunning scenery throughout. The hosts on board (Carol and Carlo) were exceptional - making delicious and varied food each day. And little Mattias - the best boat poodle there ever was! What are you waiting for - book this adventure. Thank you Andrea, Carol and Marta for an unforgettable week.

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

10/12/2026

Lee T.

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GB

Wow I had a fantastic week with Alessandro and Carlo, they both were so kind and caring and went out of their way to ensure we had a fantastic trip, even when the weather on the last 2 days meant we had to change the itinerary Ale found a way to ensure we didn’t miss out on visiting new places. Carlo was a fantastic host, his cooking was amazing and so much to eat every day as well as his friendly smile and always there to help. Alessandro, what a great guy, a great skipper, always ensuring we were happy and safe and would go out of his way to take us ashore and find the best restaurants. I have made a new friend for life and will be back next year 🤣 Thanks to you both for a memorable holiday
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From Mykonos to Athens by sail, with skipper and on-board kitchen

10/7/2026

manuela c.

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IT

Annalisa and Emanuel were professional and nice, we unfortunately had the worst week of wind in sailor's memory and we were forced to always stay still without sailing except for 3 hours on the first day so I can't talk about the cruise destinations except for syros that they propose and that, unlike other islands, it is not crowded and therefore maintains something of the Greek spirit with beautiful villages and has beautiful trekking and beaches (the beaches unfortunately due to wind were not frequentable but I saw them in the treks). Beautiful and spotless boat absolutely comfortable. What can I say? Hope to see you again next year! Maybe with better luck for the climate! Thank you

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