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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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4.7

Whale watching cruise with WWF guide in the Corfu archipelago

Greece: Ionian Islands

6 days - 7 nights

3 departures available

July - August

Starting from

€1,041

€989

Per person

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5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

4 departures available

July - September

Starting from

€1,000

€900

Per person

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5.0

Super!

The Saronic Islands sailing, skippered and on-board kitchen

Greece: Saronic Islands and Athens area

6 days - 6 nights

5 departures available

May - October

Starting from

€950

€855

Per person

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4.8

Super!

Catamaran with Chef in the magical sea of the Ionian Islands - Holiday for SINGLES

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€1,450

Per person

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5.0

Super!

From Santorini to Milos by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

July - August

€1,050

Per person

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Zakynthos sailing escape - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

7 departures available

May - October

Starting from

€779

€701

Per person

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New

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

Greece: Saronic Islands and Athens area

7 days - 7 nights

16 departures available

May - November

Starting from

€585

€527

Per person

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4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

2 departures available

August

€1,290

€1,190

Per person

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5.0

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

Greece: Sporades

6 days - 7 nights

9 departures available

May - September

Starting from

€650

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

7 departures available

July - October

Starting from

€779

€701

Per person

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4.9

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

5 departures available

May - October

€990

Per person

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New

A perfect August? The Ionian Islands on a sailing boat!

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

Starting from

€690

Per person

Why book a holiday with Sailsquare?

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Reviews - Yacht sailing holidays & skippered tours in Greece

1907 reviews

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Sailing in the Cyclades

04/22/2026

Miguel M.

-

Spain

Exceptional experience!! Yann is a skipper who knows the navigation area and the most suitable anchorages and ports well. In addition to being an excellent sailor, he is an endearing person who seeks the well-being of his "crew", carrying out activities on land such as hikes or visits to interesting places that give added value. His boat "[hidden]" is a sailboat of the highest level, very comfortable and designed to sail in extreme conditions and therefore absolutely safe. Yann keeps it in pristine condition and is spotlessly clean. In short, it is a highly recommended experience.
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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.

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.

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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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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