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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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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

18 departures available

April - October

Starting from

€480

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

23 departures available

May - November

Starting from

€650

€618

Per person

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4.8

Super!

Greek Islands Catamaran Cruise - Saronic

Greece: Saronic Islands and Athens area

7 days - 7 nights

22 departures available

April - October

Starting from

€820

Per person

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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

12 departures available

May - September

Starting from

€1,000

€890

Per person

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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

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

Greece: Ionian Islands

7 days - 7 nights

12 departures available

June - September

Starting from

€600

€540

Per person

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4.8

Super!

Paros Serifos Kytnos the fantastic Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August

€950

Per person

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4.8

Super!

Discovering the wild Peloponnese

Greece: Peloponnese

7 days - 7 nights

One departure available

July

€880

Per person

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4.8

Super!

Route to the South: The Small Cyclades and spectacular Santorini

Greece: Cyclades

7 days - 7 nights

One departure available

September

€850

€765

Per person

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5.0

Super!

Sailing in the Aegean, the sea of the Gods!

Greece: Cyclades

7 days - 7 nights

One departure available

May

€500

Per person

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4.9

Super!

Rhodes Kalymnos South Dodecanese on magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

2 departures available

July - August

Starting from

€1,000

Per person - min 2 pax

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4.9

Super!

From Samos to Kos Dodecanese North on a magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

2 departures available

July - August

Starting from

€1,000

Per person - min 2 pax

Why book a holiday with Sailsquare?

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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

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.

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

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

323 reviews

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Sailing in the Cyclades

04/22/2026

Miguel M.

-

Spain

Exceptional experience!! Yann is a skipper who knows the navigation area and the most suitable anchorages and ports well. In addition to being an excellent sailor, he is an endearing person who seeks the well-being of his "crew", carrying out activities on land such as hikes or visits to interesting places that give added value. His boat "[hidden]" is a sailboat of the highest level, very comfortable and designed to sail in extreme conditions and therefore absolutely safe. Yann keeps it in pristine condition and is spotlessly clean. In short, it is a highly recommended experience.
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Sailing cruise in the Greek islands - The Saronic Islands

04/15/2026

Goutham B.

-

Germany

I had a wonderful week of sailing with this team. Skipper is super cool and I enjoyed his company a lot. He was happy to customize the sailing plan according to each of our requirements and was friendly to even cook for us a few times (The pasta was delicious). Bertrand even allowed me to stay on the boat for few extra days at Aegina. However, for my bad luck, an unfriendly couple was part of the crew and they were neither willing to pay for the skipper's food, nor willing to cook which was clearly mentioned in the advertisement as the responsibility of the whole crew. Even then the skipper was cool enough to invite us all to dinner in order to build up a family feeling between the crew members. Despite all this effort, It's unfortunate to see them giving a bad review about their sailing experience here. But other than this, personally I enjoyed the whole sailing week with Bertrand and his team. I am looking forward to sail with your team in the future.

Sailing cruise in the Greek islands - The Saronic Islands

04/15/2026

Thomas S.

-

United Kingdom

The captain (Alex) asked us to lie to the police as soon as we got there about being his friends and not chartering this boat. Something about not having a charter lisence, which made us feel very uncomfortable, even though Bertrand now denys it. The toilets stank and the shower was very uncomfortable to use, but I guess thats just how boats are. It leaked when it rained and it is fairly cramped, and we left asking why we paid that price for that boat. We didn't feel like we got value for our money at all and the organiser was very rude to us when we brought up our concerns. At least the islands were nice.
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Secret Aegean with skipper and kitchen on board - Rhodes to Kos

10/22/2025

Douglas B.

-

United Kingdom

An extraordinary experience that exceeded all expectations

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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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