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Private yacht sailing holidays with skipper in Greece

Greece is one of the best sailing holiday destinations in the world! Over 16,000 km of beautiful coastline offers countless exciting itineraries. A whole boat reservation allows groups of family or friends the freedom to - with your skipper - craft a personalised holiday with activities and routes that tailored to your specific holiday style and wishes.

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4.8

Super!

Premium

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

Greece: Saronic Islands and Athens area

6 days - 7 nights

8 departures available

August - October

Starting from

€1,300

€1,040

Per person

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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€570

Per person

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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

8 departures available

August - October

Starting from

€570

Per person

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4.7

Super!

Luxury catamaran cruise in the Cyclades

Greece: Cyclades

7 days - 7 nights

5 departures available

September - November

€1,000

Per person

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4.8

Super!

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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4.8

Super!

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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4.8

Super!

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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4.9

Super!

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

October

Starting from

€950

Per person

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5.0

Super!

Kefalonia to Corfu

Greece: Ionian Islands

6 days - 6 nights

One departure available

August - September

€900

Per person

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5.0

Super!

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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4.9

Super!

Rhodes Kalymnos South Dodecanese on magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,200

Per person - min 2 pax

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4.8

Super!

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

Why book a holiday with Sailsquare?

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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.

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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Private yacht sailing holidays with skipper in Greece

417 reviews

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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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Sailing cruise in the Greek islands - The Saronic Islands

08/13/2026

Bruno P.

Not even closer to the good experience we had last year.

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

08/13/2026

Florian H.

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DE

The Tour was great - we had a marvelous time with our family (including two 14-year-old boys) and the other guests. Skipper Tom and our host Aga are very kind and professional. We enjoyed the cuisine and the tour plan including a trip to Hydra. Tom was one of the best skippers I have been with, combining an eye for safety with calm and decisive seamanship. Aga made everything else possible be it recommending places and restaurants but also considering allergies and other specifics. The sea and the landscape are fantastic. Big thanks to the entire team!

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6 reasons to choose a whole boat reservation in Greece for your next sailing holidays:

  • Experience the beauty of one of the world’s best sailing destinations.
  • Explore your choice of the thousands of Greek islands.
  • Find holidays throughout the Ionian islands, the Cyclades, the Dodecanese, the Saronic islands and the Athens area.
  • Travel with maximum freedom, working with your skipper to construct a holiday perfect for your friends and family.
  • Discover Greece at your pace.
  • Embrace quality family or friend time with an original holiday and create unforgettable holiday memories.

Travelling in Greece in a whole boat with a skipper

What a whole boat sailing holiday offers

Sailing holidays are a brilliant opportunity for groups of family and friends to come together and create special holiday memories. Booking a whole boat allows you some luxuries you may not find when sharing the boat with travellers. One particular luxury that could make a great different to your holiday structure is the freedom of your itinerary - which may be especially relevant when travelling in Greece where there is such an abundance of special islands and destinations to visit. Reserving a whole boat then allows you to work with your skipper to tweak and tune the holiday to suit you and your friends and family.

Locations in Greece for a whole boat sailing holiday

Across the Ionian islands, the Cyclades, the Dodecanese, the Saronic islands and the Athens area you can find holiday listings with whole boat booking availability. If you come across an experience either isn’t or doesn't explicitly appear as a whole boat listing, you can reach out to the organising skipper through the “contact the skipper” button present on each holiday listing to understand their upcoming availability.

Tips to help you to better plan for your next sailing holidays in Greece:

All you need to know about your next cruise in Greece aboard a sailboat.

When to go to Greece for a sailing holiday & how long should I visit?

The Greek climate is pleasant and generally suitable for sailing holidays throughout the year. Travellers might want to consider a sailing holiday in Greece during the slightly quieter months of May, June, September, or October when weather conditions are still generally warm. Depending on the style of sailing experience you are looking for, each group of islands has their unique personality, and each island it’s special charm. Travelling with a local, experienced skipper means that you are able to travel to the popular destinations as well as lesser known spots, tucked away from mainstream tourism. Again, depending on the set of islands you are visiting, the recommended duration will differ. We recommend a minimum of two weeks to discover the Cyclades and the Dodecanese. If you have less time, we recommend looking at holidays in the Ionian, Saronic, Sporades and Crete.

Transport options to and from your holiday in Greece & sailing with a family

Greece is home to a number of international airports, including Athens, Corfu, Kos, and Kefalonia. Prices will vary substantially depending on the month, you may find cheaper alternatives in the months before and after the peak months of July and August. There is a highly developed network of ferries that are a main form of transport, and maybe necessary to reach your skipper. Your skipper will be best placed to give you advice on transport options according to the specific embarkment, disembarkment and season of travel. Greece is a location that is particularly family sailing holiday friendly, this as there is generally a warm climate, plenty of mooring options, and many facilities for activities such as water sports.

Greece: the best travel ideas

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