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Sailboat yacht sailing holidays & tours in Greece

Discover more than 9 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

2 departures available

October

€1,300

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

2 departures available

October - November

€585

Per person

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4.9

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

October

€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

2 departures available

October

€570

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

3 departures available

October

€570

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

5 departures available

October - November

€700

€665

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

3 departures available

October

Starting from

€1,200

€500

Per person

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5.0

Exclusive sailing week among the wonders of Ionian Greece

Greece: Ionian Islands

6 days - 7 nights

One departure available

October

€1,200

Per person

Why book a holiday with Sailsquare?

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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

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

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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

1999 reviews

Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

10/6/2026

Victoria S.

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GB

A fantastic week of sailing, good food and good company. Alessio was really helpful in all aspects of the trip. The boat was very cosy, well equipped and comfortable. Would recommend to anyone who wants to try a sailing holiday for the first time.
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

10/6/2026

Ceren G.

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NL

It was an amazing week. Thank you Andrea and Carol for everything. Hope to see you again next year.
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Saronic Islands and surroundings of Athens

10/5/2026

Erjon G.

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DE

Andrea is great Captain, we had amazing time even the weather was not our side still we enjoyed a lot.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

10/5/2026

Aldo B.

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AT

My partner and I had an amazing week at sea, and a big part of that was our crew. Alessandro, our skipper, was highly professional and made us feel safe and well looked after at every moment. Carlo, our steward, was warm, attentive and always ready with a smile. The route between Corfu, Paxos and Antipaxos was stunning, with crystal-clear water and charming harbours. The crew went out of their way to make the trip special. We explored sea caves by dinghy, played an unforgettable volleyball match in the middle of the sea, and got great restaurant recommendations for our evenings ashore. Carlo's lunches on board were delicious, fresh and beautifully prepared. Alessandro and Carlo truly made this trip. We would happily sail with them again and recommend them to anyone looking for a relaxed, fun and well-organized holiday on the water. Thank you both!

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