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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

4 departures available

September - October

€1,300

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

4 departures available

October

€570

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

4 departures available

September - October

Starting from

€570

Per person

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5.0

Super!

Saronic Islands and surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September

€620

Per person

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4.9

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October

€750

Per person

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4.7

Luxury catamaran cruise in the Cyclades

Greece: Cyclades

7 days - 7 nights

3 departures available

October - November

€1,000

Per person

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4.9

Super!

Cyclades from Milos to Milos

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

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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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5.0

Super!

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

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

€760

Per person

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5.0

Super!

The enchantment of the sea: Lefkada, Ithaca, Kefalonia and the smaller islands

Greece: Ionian Islands

7 days - 7 nights

One departure available

October

€600

Per person

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4.8

Super!

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€600

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

One departure available

September

€1,000

€800

Per person

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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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Sailing holidays that suit all budgets

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

466 reviews

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

09/15/2026

AnnMarie S.

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US

Amazing vacation! I would compare it to somewhere between camping and glamping, but on the sea! We saw the most beautiful beaches, sunsets, and sunrises. We sailed along side dolphins, explored caves, and even saw sea urchins and octopus when we were snorkeling. Caroline was our chef an overall caretaker. She catered to our every need and the best meals we had all week were the breakfasts and lunches that she cooked for us! The boat fits up to six guests. Two of the three rooms are extremely small so if you go with friends, you will be sleeping in the same bed since there is only one bed per room. There is also no indoor shower. You shower in your bathing suit out in the open on the back of the boat. I would highly recommend privatizing the boat if you go with a group of friends. We thought we had done so, but then we found out at the last minute that there was miscommunication and a man was joining us four girls. He was very nice, but we would’ve preferred to only have one girl per small room versus doubling up and having to share space/a bathroom with a man. Overall it was a fabulous experience and I would most definitely do it again!
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Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

09/14/2026

Evi (Paraskevi) P.

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GR

[hidden] is a wonderful classy and spacious boat very well maintained so makes you feel safe and i couldn't get enough of the sunbathing on the lounge mattress on the bow of the boat. Captain Alessio is a down to earth,kind and calm person making this an Ideal combination for enjoying some relaxing holidays. Plus he has a lot's of knowledge around various subjects so it's really enjoyable talking to him. He made sure ,during our whole week in the Argosaronic gulf, to find for us the best anchorage with crystal clear waters. As i was the only person on board not speaking Italian captain Alessio and the rest of the crew never left me outside a conversation and always either translating or communicating in English.. Had a fantastic relaxing time, the chance to discover some sight seeing on the area make new friends and explore the local food culture. Thank You Captain.
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Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

09/14/2026

Lorenzo G.

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GB

A really enjoyable sailing holiday and a great way to discover the Saronic Islands. The trip offered a good mix of sailing, relaxing, and visiting interesting places, including destinations with plenty of cultural and historical interest. The boat was very well maintained and well equipped, so life on board was comfortable and easy. We had good food, good company and a very pleasant atmosphere throughout the trip. There were also plenty of opportunities to get involved in the sailing, which I particularly enjoyed. The skipper was friendly, easy-going, and always helpful, which made the whole experience very enjoyable. A very good holiday overall, and one I would happily recommend.

From Skiathos to Athens

09/14/2026

Elizabeth B.

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AR

Beautiful week of sailing. Fantastic places

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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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