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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

11 departures available

July - October

Starting from

€1,200

€1,080

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

10 departures available

July - 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

13 departures available

July - October

Starting from

€570

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

2 departures available

August - September

Starting from

€650

€585

Per person

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4.8

Super!

Sailing among the Islands of Ulysses. Stewardess on board

Greece: Ionian Islands

6 days - 7 nights

2 departures available

August

Starting from

€800

€720

Per person

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4.8

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

15 departures available

July - November

Starting from

€700

€665

Per person

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4.8

Super!

Catamaran in the Saronic Islands: Hydra, Poros, Aegina and wild bays

Greece: Saronic Islands and Athens area

7 days - 7 nights

6 departures available

July - August

Starting from

€1,450

Per person

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4.9

Super!

From Kos to Rhodes, the South Dodecanese on a magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€1,000

Per person - min 2 pax

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4.9

Super!

Fast Sailing Experience between Authentic Islands and Good Food

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

4 departures available

September - October

Starting from

€600

€540

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!

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

Greece: Cyclades

6 days - 6 nights

2 departures available

September

€1,000

Per person

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Reviews - Private yacht sailing holidays with skipper in Greece

347 reviews

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From Mykonos to Milos

07/2/2026

Maximiliano S.

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AR

Great experience, we traveled 2 couples and we are very grateful for all the attention provided by Andrea, we sailed through all the cyclades and she made us enjoy and share great moments and know places. Unique and incredible and having fun with our travel companions Elena, Patrick and Toni, who were very funny. A sublime experience.

In the heart of the Cyclades, from Milos to Athens (Lavrio)

07/2/2026

Christine H.

-

DE

This was my first sailing trip and I was able to have an exciting and valuable experience. Unfortunately, we could not follow the originally planned route due to the weather. But Andrea quickly had an alternative ready. Unfortunately, the weather conditions were sometimes challenging for me despite the changed route. But Andrea led us confidently through them and I guided myself safely at all times. Whenever possible, Andrea responded to our wishes, and he also contributed many of his own suggestions and ideas, which certainly simplified the decision-making process within our group. At the same time, I would have liked to see more proactive communication regarding the respective daily schedules. The boat has already been allowed to cover many nautical miles, which can be seen in one place or another. But everything you need is available. For me as a sailing novice, the distances covered could have been a little shorter and the rest periods more extended. But this was certainly also due to the changed, longer route. Thank you Andrea for this experience and your support! 😌

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

07/1/2026

Rory D.

-

IE

Francesco was incredibly nice, welcoming and good fun to be around. He was very accommodating, thoughtful and was always looking for a way to make our trip more enjoyable. He also sought to align the route with our preferences. The boat was very clean, well equipped and the beds were much larger than they appear in the photos! As a skipper, he was very organised and experienced. He was always tracking the weather and considered our safety a priority. On top of that, he knew the islands, bays, harbours and routes inside out!

Catamaran week among the islands of Ionian Greece

07/1/2026

Daniele D.

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IT

Greece is magnificent, I have visited it several times but, believe me, with Nico I experienced it for the first time! An experienced captain, he knows every corner of paradise and takes you there, where you just need to dive or have an aperitif in the most characteristic marina... A sunny, kind, helpful person, able to meet everyone's needs and turn it into an opportunity for everyone! ... great cook and fisherman... Fish n Chips and Seared Tuna with Sesame just amazing. I have the feeling that I have lived not only a magnificent experience but that I have also found a friend... Nico see you next June !!

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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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