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Yacht sailing holidays & skippered tours in Greece

Discover more than 24 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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5.0

Super!

The Saronic Islands sailing, skippered and on-board kitchen

Greece: Saronic Islands and Athens area

6 days - 6 nights

2 departures available

October

€950

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

€1,305

€1,044

Per person - min 2 pax

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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

€676

Per person - min 2 pax

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3.0

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

Greece: Dodecanese

7 days - 7 nights

2 departures available

October

Starting from

€829

Per person

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New

Premium

All inclusive sailing cruise on Dufour 48 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€1,785

€1,575

Per person

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New

Premium

All inclusive catamaran cruise on a Bali 4.2 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€2,060

Per person

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3.0

Zakynthos sailing escape - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

Starting from

€779

Per person

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3.0

Where the blue feels like home: the Ionian islands - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

Starting from

€779

Per person

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3.0

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

Per person

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New

Corfu: sailing, dream bays and walks in the villages - hostess on board

Greece: Ionian Islands

6 days - 6 nights

4 departures available

October

Starting from

€1,200

€500

Per person

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New

Premium

All inclusive catamaran cruise on Excess 11 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€1,875

Per person

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5.0

Exclusive sailing week among the wonders of Ionian Greece

Greece: Ionian Islands

6 days - 7 nights

2 departures available

September - October

Starting from

€1,200

Per person

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Reviews - Yacht sailing holidays & skippered tours in Greece

2022 reviews

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

08/16/2026

Paolo N.

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IT

A wonderful experience, but with several critical issues to improve Overall it was certainly a wonderful experience, which allowed us to experience the sea, meet new people and share really pleasant moments. Precisely for this reason, however, I believe it is important to underline some major organizational shortcomings that have negatively affected a part of the trip and which, in my opinion, should absolutely be improved. The first concerns the complete disorganization of the evenings on land. We expected that, since it was a real flotilla made up of 5 boats, reservations would be planned and organized in advance in the clubs, so that we could all be together and experience the evenings as a single group. Instead, we often found ourselves having to organize ourselves, losing precisely that group and flotilla dimension that we expected from the trip. The excursions were also unclear and not always well organized. We would have liked to have had more opportunities to reach particularly beautiful sea areas and, above all, to live some organized experiences to enjoy the sunset from the sea, which on a sailing trip should represent one of the most beautiful moments. Another critical issue was the lack of music on the individual boats, despite the fact that we had been told that the system was working. Considering the type of trip and the spirit of the holiday, having the possibility to put music on board was an element that we expected and that would contribute a lot to the atmosphere. We also had the problem of the rowing tender, due to the engine not working. It is understandable that technical problems may occur, but it would have been important to find an alternative solution quickly, especially considering the need to move smoothly from the boat to land. Finally, and perhaps this is the thing I regretted the most, the final evening was completely unorganized. On a group trip and especially in a flotilla of 5 boats, I would have expected a final moment organized to be all together, celebrate the end of the trip and say goodbye. The lack of a real final goodbye was, in my opinion, a serious lack: after a week shared together, it would have been the least to expect a moment dedicated to closing the experience all together. In conclusion, there is certainly the memory of a beautiful experience and a holiday that could have been really fantastic, but precisely for this reason I believe that these aspects must be taken seriously into consideration. With more organization of activities, evenings and group moments, the trip could have reached a much higher level.
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Different flotilla in Ionian Greece: nature, new friends and fun

08/16/2026

Nensi G.

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IT

Ideal holiday to meet new people. Seeing beaches that are unreachable without a boat. Party and much more
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Whale watching cruise with WWF guide in the Corfu archipelago

08/15/2026

Ilka B.

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CH

We sailed from Santa Maria di Leuca to the Greek islands around Corfu – a fantastically beautiful trip that I will never forget! Roco was our captain and just great! He navigated us safely and confidently, was always friendly and warm and immediately made us feel welcome on board. Donatello was our whale watching guide – and he really is the best! With his great knowledge, his humor and his incredible enthusiasm for whales and dolphins, he not only imparted a lot of knowledge to us, but also shared his own fascination with us. He tirelessly looked out for animals and chose the best routes for us. And with success: We were able to observe sperm whales, beaked whales and dolphins. These encounters were beautiful and incredibly touching! The group on board was also great. From the very beginning, Donatello has made sure that everyone feels comfortable and gets along well with each other. So we had a wonderful time with exciting conversations, lots of laughter, fine food, games together and of course many fascinating moments on the water. The whole trip was just fantastically beautiful – a perfect mix of sailing, nature, adventure and wonderful people. Many thanks again to Roco, Donatello and the whole team for this unforgettable time! 💙🐋⛵

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

08/13/2026

Aurora G.

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IT

It was the first experience on a boat... unique and spectacular! Annalisa and Emanuel were able to make us feel immediately at ease. Both, experienced and close-knit sailors, emanate an immense passion for what they do, able to transmit it to all their companions. Two sunny, kind, helpful and knowledgeable people who take you to discover fantastic and exclusive places; deserted beaches and islands, far from the chaos, where it is possible to admire all the beauty of the Greek islands both during the day and during the night with breathtaking starry skies. The boat is well organized, allowing you to move freely and safely even in small spaces. Moreover, Annalisa and Emanuel are also fantastic cooks, capable of preparing exquisite delicacies with local flavors and in great abundance! Also thanks to our travel companions, we can say that we embarked as perfect strangers and then disembarked feeling part of a group of friends. Thank you very much Emanuel and Annalisa for this unforgettable experience... See you soon!

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