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

Greece: Saronic Islands and Athens area

6 days - 7 nights

7 departures available

August - October

Starting from

€1,300

€780

Per person

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Big and luxurious 60ft catamaran in Saronic Islands - best local experiences

Greece: Saronic Islands and Athens area

6 days - 7 nights

7 departures available

August - October

Starting from

€2,500

€2,250

Per person

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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

4 departures available

September - October

Starting from

€570

Per person

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

Greece: Ionian Islands

7 days - 7 nights

6 departures available

September - October

Starting from

€570

Per person

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4.8

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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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South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€650

Per person

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Catamaran with chef in the magical sea of the Ionian Islands

Greece: Ionian Islands

6 days - 7 nights

3 departures available

August - October

Starting from

€900

Per person

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Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

3 departures available

September - October

Starting from

€600

€540

Per person

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Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€650

Per person

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The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

€750

Per person

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5.0

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From Skiathos to Athens

Greece: Sporades

7 days - 7 nights

One departure available

September

€620

Per person

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5.0

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Catamaran week among the islands of Ionian Greece

Greece: Ionian Islands

6 days - 6 nights

2 departures available

August - September

Starting from

€1,125

Per person

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Reviews - Yacht sailing holidays & skippered tours in Greece

2058 reviews

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Big and luxurious 60ft catamaran in Saronic Islands - best local experiences

08/24/2026

Sonia B.

Fantastic week! Greg is an experienced skipper, in his hands you feel absolutely safe in the face of any situation. As much as possible, Greg will accommodate your preferences with respect to sleeping in the bay or in small ports. Aga is a fantastic hostess, always attentive to her guests, she tries to satisfy any need with a smile. He will prepare fantastic lunches for you, always imaginative and with local products/Greek recipes. Aga and Greg will not only be your hosts, but an integral part of your trip as pleasant company. The boat really has everything you need to enjoy the experience to the fullest, the spaces are large enough to be able to carve out moments for yourself.
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Different flotilla in Ionian Greece: nature, new friends and fun

08/24/2026

Lidia C.

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IT

It was an experience that I would do again without any doubt! I had a lot of fun, I had a good time and I really managed to unplug from everyday life. We visited beautiful places, shared unforgettable moments and had lots of laughs, making this holiday special in every way. A special thanks goes to our captain Vincenzo and Nina, who were fundamental for the success of this experience. Always available, attentive and caring, they were able to put us at ease from day one with small but precious attentions. In addition, they have been a constant point of reference, guaranteeing company, professionalism and clarity throughout the organization of the week. The organization of Different Sailing was also positive and pleasant. There were some small discrepancies compared to activities initially communicated, such as the Hawaiian party and the fluorescent party, which for organizational reasons did not take place. However, this did not compromise the overall experience, which was really fun, well organized and full of moments to remember. In conclusion, I bring with me wonderful memories, new friendships and the desire to start again as soon as possible. An experience that I definitely recommend to those who want to discover enchanting places, experience the sea from a unique perspective and share authentic moments with fantastic people.

Different flotilla in Ionian Greece: nature, new friends and fun

08/24/2026

claudio m.

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IT

Beautiful experience
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Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

08/24/2026

Jacopo S.

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IT

All very nice and well organized, but for me, who was the very first experience of this kind, it had to be specified that you have to help the skipper, almost "mandatorily", in the different phases of mooring and navigation

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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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