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Yacht sailing holidays & skippered tours in Greece

Discover more than 58 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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4.8

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

One departure available

July

Starting from

€1,300

€1,170

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

July - August

Starting from

€570

Per person

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4.8

Super!

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

July

Starting from

€650

€585

Per person

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5.0

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

Greece: Ionian Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€570

Per person

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4.8

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

4 departures available

July - August

Starting from

€700

€665

Per person

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5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

2 departures available

July - August

Starting from

€750

Per person

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4.7

Whale watching cruise with WWF guide in the Corfu archipelago

Greece: Ionian Islands

6 days - 7 nights

One departure available

July - August

€1,052

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

2 departures available

July

Starting from

€600

€540

Per person

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4.8

Super!

Catamaran in the Saronic Islands: Hydra, Poros, Aegina and wild bays

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

July - August

Starting from

€1,450

Per person

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4.9

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

June - July

Starting from

€1,080

Per person

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4.9

Super!

From Samos to Kos Dodecanese North on a magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

July

Starting from

€1,000

Per person - min 2 pax

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4.9

Super!

From Kos to Rhodes, the South Dodecanese on a magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

July

Starting from

€1,000

Per person - min 2 pax

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 - 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.

-

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.

-

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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