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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.

99

experiences

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4.9

Fine Dodecanese to Samos with a fast-cruiser boat

Duration:

6 days - 7 nights

Greece:

Dodecanese

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+3 travellers

have booked

€930

Per person

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5.0

THE PEARLS OF THE DODECANESE

Duration:

7 days - 7 nights

Greece:

Dodecanese

Give this experience a try!

Starting from

€1,083

Per person

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5.0

The Dodecanese: 10 Days, 9 Islands, A Luxurious and Fast Boat

Duration:

10 days - 10 nights

Greece:

Dodecanese

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+2 travellers

have booked

€1,341

€1,490

Per person

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5.0

Lose yourself in the magic of the Southern Ionian Islands

Duration:

7 days - 6 nights

Greece:

Ionian Islands

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+7 travellers

have booked

Starting from

€900

Per person

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4.9

From Samos to the Small Cyclades by sailboat

Duration:

6 days - 7 nights

Greece:

Cyclades

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+4 travellers

have booked

€960

Per person

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4.6

Unique experience through the Corinth Canal, from the Ionians to Athens

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

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+2 travellers

have booked

€1,100

Per person

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Relaxation in the Ionian islands on a catamaran

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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+3 travellers

have booked

Starting from

€1,000

Per person

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4.7

Big and luxurious 60ft catamaran in Cyclades - best local experience

Duration:

6 days - 7 nights

Greece:

Cyclades

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+4 travellers

have booked

Starting from

€1,796

€1,890

Per person

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4.7

Best local sailing experience on 50ft monohull away from the crowds

Duration:

6 days - 7 nights

Greece:

Cyclades

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+28 travellers

have booked

Starting from

€893

€940

Per person

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5.0

From Kos to Athens via the Dodecanese, the Sporades and the Cyclades

Duration:

9 days - 10 nights

Greece:

Dodecanese

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+7 travellers

have booked

€890

Per person

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4.9

Fast cruising Cicladi Occidentali

Duration:

6 days - 7 nights

Greece:

Cyclades

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+6 travellers

have booked

Starting from

€960

Per person

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4.7

Big and luxurious 60ft catamaran in Cyclades - best local experience

Duration:

6 days - 7 nights

Greece:

Cyclades

Give this experience a try!

Starting from

€1,500

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

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

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 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

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

5 reviews

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Sailing Cyclades

04/15/2024

yannis b.

-

France

Séjour incroyable avec Yann ! Très attentif, drôle et chill dans toutes les situations, dans un bateau très confortable !
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In the sea of Ulysses! Discovering the most beautiful islands

08/29/2022

roberto c.

-

Italy

Che dire.... Bellissima vacanza. Baie e porticcioli che Leo conosce a menadito. E' un velista esperto e ha dimostrato di saper gestire la barca in tutta sicurezza anche in situazioni avverse dovute al maltempo o alle carenze di altre barche vicine di ormeggio. E' simpatico, socievole e fa da mangiare bene. Imperdibile il capretto marinato cotto alla brace sul berbecue della barca. Grazie Leo.
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Walking around the Cyclades - Exclusive boat

08/2/2022

Nurit R.

-

United States

We had the most amazing family vacation around the Cyclades islands with Max and Cori this summer. Knowledgeable and accommodating at all times, they made our week with them the best and most memorable ever. They know the best islands, local tavernas, beautiful private beaches and coves. They even taught my husband how to sail and allowed me and my daughter to take the wheel. The whole week we spent with them was unforgettable, the food delicious and we can’t wait to do it again!
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South of Lefkas between pristine nature bays of Meganisi and myths of Ithaca

08/20/2021

Victoria M.

-

United Arab Emirates

Our family of four (2 adults and two children aged 8 and 10) have just finished an amazing 14-day sailing trip with Francesco. We visited so many beautiful islands, coves and ports including Zakynthos, Kefalonia, Ithica, Lefkada, Kalamos, and Kastos. Francesco was a brilliant captain and we feel so grateful to have selected him. He was wonderful with our children, very relaxed whilst being extremely conscious of safety, and went out of his way to ensure that we had a well-balanced holiday that included sleeping in secluded bays, visiting charming fishing villages, eating in some wonderful tavernas and relaxing as a family. We would highly recommend Francesco for your Greek sailing adventure!

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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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