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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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4.9

Super!

Baie and fast sailing from Milos to Paros

Greece: Cyclades

6 days - 7 nights

One departure available

September

€890

Per person

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4.9

Super!

Chios, Oinoussa, Fournoi and Samos on a magnificent 15-meter boat

Greece: North Egean Islands

7 days - 7 nights

One departure available

June

€800

Per person - min 2 pax

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4.9

Super!

Scoprire il fascino del Nord Egeo con navigazioni veloci

Greece: North Egean Islands

6 days - 7 nights

One departure available

June

€790

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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4.8

Super!

Following the North Star, from Lefkada to Corfù

Greece: Ionian Islands

6 days - 7 nights

One departure available

September

€650

€585

Per person

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New

Milos, Folegandros and the fantastic Southern Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

July - August

€1,050

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

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5.0

Ionian Greece aboard a Catamaran with Skipper/Chef

Greece: Ionian Islands

6 days - 7 nights

3 departures available

July - August

Starting from

€1,900

Per person

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5.0

Catamaran week among the islands of Ionian Greece

Greece: Ionian Islands

6 days - 6 nights

14 departures available

June - November

Starting from

€1,099

Per person

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4.9

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

6 departures available

June - October

Starting from

€950

Per person

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New

Ios, Santorini, Anafi: the breath of the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August

€1,150

Per person

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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

9 departures available

June - November

Starting from

€585

€527

Per person

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Reviews - Yacht sailing holidays & skippered tours in Greece

1918 reviews

Sailing paradise in Greece on a big 50 ft boat: the best local experience

06/8/2026

Ewout (Eduardo) G.

Excellent week of sailing & chilling in beautiful bays & ports!

Sailing paradise in Greece on a big 50 ft boat: the best local experience

06/7/2026

Suzanne K.

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IE

Overall we really enjoyed the trip. We were very well looked after by Aga & Arnie. Breakfast & lunch was great (vegetarian). The rest of the guests were lovely as well. The schedule was very chilled with plenty of time to relax on and off the boat. The trip to the vineyard was definitely a highlight! Worth remembering that destinations will depend on weather, so you may not get to visit all the places mentioned on the itinerary. A great experience & would recommend 👌

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

06/6/2026

Annina P.

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CH

We had an unforgettable time in the Cyclades! Our skipper Dimitris introduced us to sailing, which was totally new for us but totally exciting and a very nice experience on the sea. It was a great mix of sailing and time on land to explore new places. We enjoyed it very much & highly recommend it:)
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Sailing cruise in the Greek islands - The Saronic Islands

06/4/2026

Sandrine B.

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FR

All the ingredients were there to have a great time. A week that I am not ready to forget, Alexandre adapted this cruise to my desires, he was also very careful to make these few days very pleasant. We agreed together on the destinations in the Saronics, I was able to discover very beautiful islands and participate in the sailings. I learned a lot, he answered my questions about the operation of a boat, even the most absurd ones... We also had a good laugh. We had interesting and enriching discussions, thank you also for that. I had a very comfortable cabin that I enjoyed returning to in the evening. A big thank you to Alexandre for his professionalism and to Bertrand the owner of the boat who allowed me to live this week à la carte. See you soon on the water and/or on dry land.

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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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