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Yacht sailing holidays & skippered tours in Greece

Discover more than 22 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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4.9

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

October

€990

Per person

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4.5

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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4.8

SHARE & SAIL - 5 days Exploring & Relaxing at the heart of Cyclades

Greece: Cyclades

5 days - 5 nights

One departure available

October

€880

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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4.5

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

€1,470

€1,323

Per person - min 2 pax

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

Greece: Dodecanese

7 days - 7 nights

3 departures available

October

Starting from

€829

€746

Per person

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Sailing the Aegean: a Greek Islands escape - hostess on board (half board)

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October

Starting from

€929

€836

Per person

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New

Escape to the Ionian Blue - Corfu

Greece: Ionian Islands

6 days - 6 nights

4 departures available

October

Starting from

€850

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

One departure available

October

€1,200

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

1906 reviews

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Sailing cruise in the Greek islands - The Saronic Islands

04/15/2026

Goutham B.

-

Germany

I had a wonderful week of sailing with this team. Skipper is super cool and I enjoyed his company a lot. He was happy to customize the sailing plan according to each of our requirements and was friendly to even cook for us a few times (The pasta was delicious). Bertrand even allowed me to stay on the boat for few extra days at Aegina. However, for my bad luck, an unfriendly couple was part of the crew and they were neither willing to pay for the skipper's food, nor willing to cook which was clearly mentioned in the advertisement as the responsibility of the whole crew. Even then the skipper was cool enough to invite us all to dinner in order to build up a family feeling between the crew members. Despite all this effort, It's unfortunate to see them giving a bad review about their sailing experience here. But other than this, personally I enjoyed the whole sailing week with Bertrand and his team. I am looking forward to sail with your team in the future.
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Sailing cruise in the Greek islands - The Saronic Islands

04/15/2026

Thomas S.

-

United Kingdom

The captain (Alex) asked us to lie to the police as soon as we got there about being his friends and not chartering this boat. Something about not having a charter lisence, which made us feel very uncomfortable, even though Bertrand now denys it. The toilets stank and the shower was very uncomfortable to use, but I guess thats just how boats are. It leaked when it rained and it is fairly cramped, and we left asking why we paid that price for that boat. We didn't feel like we got value for our money at all and the organiser was very rude to us when we brought up our concerns. At least the islands were nice.
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Sailing in the Saronic Archipelago

10/26/2025

Lorenzo Z.

-

Italy

I chose the boat trip precisely to live the experience of sailing. We always sailed by motor, except for a few hours, in the need to dry them after a heavy rain. this even when all the other boats were sailing
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Secret Aegean with skipper and kitchen on board - Rhodes to Kos

10/22/2025

Douglas B.

-

United Kingdom

An extraordinary experience that exceeded all expectations

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