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Sailboat yacht sailing holidays & tours in Greece

Discover more than 10 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

3 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

2 departures 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

3 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

4 departures available

October

€570

Per person

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Odysseus trip to Zakynthos - Kefalonia-Ithaka

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

€890

Per person

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4.4

Premium

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

October

Starting from

€845

€676

Per person - min 2 pax

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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

6 departures available

September - November

Starting from

€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

4 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

1987 reviews

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

09/29/2026

Sailor

Excellent experience, clean and efficient boat. excellent, cuisine, top quality food, nice company, owner and staff, they do this job with feeling and dedication, Too bad we didn't get to Hydra., even if it was optional, skipper prepared but a little too plastered in his role. however, experience to be redone with this team, perhaps improving my English and with a new itinerary.
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From Milos to Athens: the fantastic Western Cyclades

09/29/2026

Jonas D.

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BE

Good times … meandering from island to island !

Cyclades from Milos to Milos

09/28/2026

Alessio P.

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IT

Fabio is a very precise and professional skipper, thanks to the weather we were able to respect all the descriptions and the boat was really beautiful and comfortable. Although it was not within his competence, we tried some really good Roman dishes. Very skilled with the scientific 😎🤣 scopone It is a thank you to the legendary Irene. Highly recommend the experience

Fast Sailing Experience between Authentic Islands and Good Food

09/28/2026

Jaouen B.

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FR

Amazing trip! Analisa and Lorenzo were born to host: good vibes, quite communication, marvelous cooks, expeirenced adventurers (know plenty of secret places) and great skippers. I highly recommend them both. If you love snorkling, maybe the Cyclades are not the best location to pick.

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