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Yacht sailing holidays & skippered tours in Greece

The Greek Archipelago has over 16,000 km of coastline, with many beaches that run for kilometres, a host of secluded bays and coves, and a rich variety of wildlife. Some say the best sailing waters in the world can be found in Greece!

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4.3

Catamaran cruise in the Saronics: between history and crystal clear sea

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

August

Starting from

€1,400

Per person

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Ionian Escape – Sailing Week from Corfu – Paxos & Antipaxos

Greece: Ionian Islands

7 days - 7 nights

4 departures available

August - September

Starting from

€800

Per person

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5.0

Come and try sailing in Ionian Greece

Greece: Ionian Islands

7 days - 7 nights

4 departures available

August - September

€667

€600

Per person

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4.6

Cruise in the Dodecanese and off Turkey on a 17m boat with chef

Greece: Dodecanese

7 days - 7 nights

3 departures available

August

Starting from

€1,300

€1,170

Per person

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4.9

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,075

Per person

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5.0

Exclusive sailing week among the wonders of Ionian Greece

Greece: Ionian Islands

6 days - 7 nights

11 departures available

July - October

Starting from

€1,200

Per person

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4.9

100% female sailing cruises

Greece: Cyclades

7 days - 7 nights

One departure available

October

€990

Per person

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4.0

Outdoor and lifestyle exploration

Greece: Peloponnese

6 days - 6 nights

One departure available

September

€815

Per person

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5.0

Sailing BenEssere in Ionian Greece

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

€1,250

Per person

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5.0

Ionian Greece with friends

Greece: Ionian Islands

5 days - 4 nights

One departure available

July

€300

Per person

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4.0

Sailing & Diving in the Small Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,390

€1,251

Per person

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4.2

Back to Corfu: to find yourself between Paxos and Antipaxos!

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€1,000

Per person

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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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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Yacht sailing holidays & skippered tours in Greece

1963 reviews

Zakynthos sailing escape - hostess on board (half board)

07/22/2026

Mirko R.

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IT

Overall positive and relaxing experience especially thanks to the staff, especially the very good cook. Unfortunately, the itinerary remains far from the most famous beaches of the islands visited (for example, it leaves out the most beautiful coast of Zakynthos where the shipwreck beach is located), it includes only one swim stop per day and consequently you arrive at the port too early. After numerous requests, on some occasions we got a second bathroom stop, which was appreciated by everyone. Excellent food, nice and friendly staff, good half board solution.

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

07/21/2026

Giulio M.

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IT

My wife and I have just spent an unforgettable week in the Sporades islands on a beautiful, extremely comfortable and welcoming sailboat. Skipper Gianfranco proved to be an exemplary professional, very prepared and always attentive to everyone's safety. Thanks to his knowledge of the area, he took us to coves sheltered from the wind, making us discover real corners of paradise In addition to his technical skills, he was able to create, right from the start, a relaxed and fun atmosphere on board; He has always been very helpful in explaining sailing techniques, advising things to see on land, showing us the best places to taste local delicacies or simply having a chat in front of a sunset. A big thank you to Gianfranco.
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/20/2026

Andrea C.

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IT

Andrea is very organized and precise. Perfect I would say for a holiday with friends

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

07/20/2026

Katia M.

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FR

Thank you to Alessandro and Carlo for a wonderful week. Tutto benissimo. It was also very pleasant to sail not far from his brother Andrea. Very good atmosphere. To be done again.

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Guides & tips


Greece

Ionian Islands, Cyclades Islands and Dodecanese are just some of the most beautiful destinations for a sailing or catamaran vacation in Greece
Guide to Greece by sailboat

Ionian Islands

Paxos, Zakynthos, Kefalonia and Lefkada are just some of the best destinations for a sailing or catamaran vacation in the Ionian Islands.
Guide to Ionian Islands by sailboat

Cyclades islands

Sandy beaches, small bays and blue and white villages have made the Cyclades a world-famous landscape, perfect for exploring by sailboat or catamaran.
Guide to Cyclades islands by sailboat

Greece: the most beautiful places to sail

Greece: departures by month

Other travel ideas

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