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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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5.0

7 islands in VIP formula - only 4 guests on board

Greece: Dodecanese

9 days - 9 nights

One departure available

September

€1,350

Per person

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4.5

CYCLADIC ESCAPE - Active Holidays: 5 days Sailing & Exploring Unknown Greece  

Greece: Cyclades

4 days - 4 nights

One departure available

October

€790

Per person

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4.3

Premium

ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

October

Starting from

€1,260

Per person - min 2 pax

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4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

October

€897

€807

Per person

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4.0

Sailing the Small Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

September - October

Starting from

€789

€710

Per person

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Sailing in the Saronic Archipelago

Greece: Saronic Islands and Athens area

6 days - 7 nights

5 departures available

September - November

€700

Per person

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4.8

Premium

Big and luxurious 60ft catamaran in Saronic - best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

October

Starting from

€2,100

€1,995

Per person

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4.8

Magical Week of Wellness Yoga, Cooking, Health, and Relaxation

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€1,200

Per person

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4.3

Premium

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

Greece: Ionian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€835

€752

Per person - min 2 pax

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5.0

Ionian Islands by Sailing: Trekking, Snorkeling and Sea Adventure

Greece: Ionian Islands

6 days - 6 nights

3 departures available

September - October

€750

Per person

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4.8

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

2 departures available

September - October

€600

€540

Per person

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5.0

Exclusive boat, you choose the route and the Cyclades islands to see!

Greece: Cyclades

6 days - 7 nights

2 departures available

September - October

€833

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 - Yacht sailing holidays & skippered tours in Greece

1879 reviews

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

09/14/2025

Madison T.

-

Canada

Wow wow wow. We had no idea what to expect when booking this trip, it exceeded every expectation. Alessandro is knowledgeable and kind, his passion for what he does shows. Carlo is sunshine in human form, the food he makes on board is incredible. Eros is the perfect addition to the boat. We felt so well taken care of the entire time. The weather was perfect early September with it being less hot than July/aug. The rooms in the boat are comfortable but it does get hot down there to sleep, I could see a usb fan being useful for sleeping. Do not hesitate to book this trip with sailing sunset.
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South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

09/14/2025

Giuseppe M.

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Italy

Francis number 1. Reliable and aware skipper!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

09/14/2025

Maude A.

-

Canada

Wonderful week with Alessandro and Carlo! We ate well and saw beautiful places. Carlo is an angel, always ready to help. Alessandro is an extraordinary skipper. He knows how to make us feel confident and safe. He too is always ready to help. The boat is beautiful. The activities were fun and the pace of the activities was good. We were also happy to be able to sail when the wind allowed. We also had a great week with the new people we met on the boat. I 100% recommend this cruise!
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

09/14/2025

Janine W.

-

Switzerland

It was perfect. Great crew. Beautiful destinations. We would definitely recommend it.

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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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