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Yacht sailing holidays & skippered tours in Greece

Discover more than 27 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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4.5

New

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

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

September - November

Starting from

€585

€527

Per person

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5.0

Catamaran week among the islands of Ionian Greece

Greece: Ionian Islands

6 days - 6 nights

5 departures available

September - November

Starting from

€1,099

Per person

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4.9

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

October

Starting from

€950

Per person

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Where the blue feels like home: the Ionian islands - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

Starting from

€779

€701

Per person

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New

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

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October

Starting from

€890

€757

Per person

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5.0

Exclusive sailing week among the wonders of Ionian Greece

Greece: Ionian Islands

6 days - 7 nights

2 departures available

September - October

Starting from

€1,200

Per person

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4.4

Premium

ATHENS Paradise - Catamaran cruise with hostess FULL BOARD

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

October

Starting from

€1,525

Per person - min 2 pax

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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

€761

Per person - min 2 pax

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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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Aegean dreams: sailing around Rhodes - hostess on board (half board)

Greece: Dodecanese

7 days - 7 nights

2 departures available

October

Starting from

€829

€746

Per person

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New

Premium

All inclusive sailing cruise on Dufour 48 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€1,785

€1,575

Per person

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New

Premium

All inclusive catamaran cruise on a Bali 4.2 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€2,060

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.

Find out before you book who's waiting for you on board

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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 - Yacht sailing holidays & skippered tours in Greece

1922 reviews

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

06/16/2026

Liubov S.

A wonderful experience! Highly recommended!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

06/16/2026

Tomas F.

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GB

No No No !!!! :(. I want more. This 7 days with Allesandro ( Skipper) and Carlo (Host) was Amazing. They will take you to the best places around Corfu. Paxos and Antipaxos are paradise. Fantastic food during sailing, healthy and everyday different. We even catch big fish during sailing, and next day bee served for lunch by Fantastic Carlo. I could write review for 100 pages, but you have to explore this wonderful trip. Greetings also for Chiara, Catarina and Luca.
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Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

06/16/2026

Stefano S.

-

IT

Pleasant week on a comfortable boat with a skipper who loves to sail even with little wind in a beautiful area.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

06/15/2026

Kamil J.

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GB

Our yacht trip with Alessandro was absolutely incredible. The weekly itinerary was perfectly planned, and every place we stayed was beautiful, with just the right amount of time spent at each destination. Carlo, our host, is the sweetest person on earth. He looked after us the entire time and made us feel truly welcome. The boat was very comfortable, and we never felt like there wasn’t enough space. Alessandro is extremely patient and such a genuinely nice person—it’s impossible not to like him. This has been one of the best experiences we’ve ever had, and we would highly recommend it to anyone considering this trip.

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