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      • Corsica
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      • Turkey
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      • Whole boat with skipper
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Private yacht sailing holidays with skipper in Greece

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.

  • Sailing Holidays
  • Greece
  • Whole boat with skipper

FLEXIBLE CANCELLATION.

Stress-free booking: you can cancel up to 24 hours before departure!

  • 2 reviews
    confirmed

    7 days of SAILING/YOGA & SUP in CYCLADES GREECE

    from 30 September - 7 nights
    Cyclades Greece
    Join in on this experience!
    790€ Per person
  • Sporades islands: Sailing holidays are more than just holidays!

    from 30 September - 7 nights
    Sporades Greece
    Join in on this experience!
    870€ Per person
  • 55 reviews
    4 discounted
    spots

    Discovering the beautiful islands of the Saronic Gulf

    from 1 October - 7 nights
    Athens and Saronic Islands Greece
    Join in on this experience!
    686 633€ Per person
  • 2 reviews
    confirmed

    7 days of SAILING/YOGA & SUP in CYCLADES GREECE

    from 7 October - 7 nights
    Cyclades Greece
    1 person interested
    in this holiday
    790€ Per person
  • Sporades Islands: Sailing holidays are more than just holidays!

    from 7 October - 7 nights
    Sporades Greece
    1 person interested
    in this holiday
    870€ Per person
  • 4 discounted
    spots

    Wine & Sail - Evia and Sporades Islands

    from 7 October - 7 nights
    Sporades Greece
    1 person interested
    in this holiday
    1.325 1.219€ Per person
  • 10 reviews
    3 discounted
    spots

    Sailboat cruise in the Ionian Islands

    from 7 October - 7 nights
    Ionian Islands Greece
    1 person interested
    in this holiday
    583 561€ Per person
  • 55 reviews
    4 discounted
    spots

    Discovering the beautiful islands of the Saronic Gulf

    from 8 October - 7 nights
    Athens and Saronic Islands Greece
    1 person interested
    in this holiday
    689 636€ Per person
  • 7 reviews
    4 discounted
    spots

    Educational week on a sailing boat - Ionian Greece

    from 9 October - 7 nights
    Ionian Islands Greece
    2 people interested
    in this holiday
    901 848€ Per person
  • 2 reviews
    almost
    confirmed

    7 days of SAILING/YOGA & SUP in CYCLADES GREECE

    from 14 October - 7 nights
    Cyclades Greece
    1 person interested
    in this holiday
    790€ Per person
  • 7 reviews
    4 discounted
    spots

    Didactic week on a sailing boat - Ionian Greece

    from 16 October - 7 nights
    Ionian Islands Greece
    2 people interested
    in this holiday
    899 846€ Per person
  • 6 discounted
    spots

    Sailing fun and sports in Corfu and Paxos. Don't miss out!

    from 21 October - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    954 848€ Per person
  • 1
  • 2

Why you should book a holiday with Sailsquare?

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Get onboard solo, with your family, or your friends

Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.

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Discover who’s already onboard

Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

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Sailing holidays that suit all budgets

Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!

Reviews - Private yacht sailing holidays with skipper in Greece

4 reviews
20 / 10
Roberto C.

Roberto C.

review about In the sea of Ulysses! Discovering the most beautiful islands August 2022

10 / 10
What can I say.... Beautiful holiday. Bays and marinas that Leo knows in a nutshell. He is an experienced sailor and has proven to be able to manage the boat safely even in adverse situations due to bad weather or the shortcomings of other nearby mooring boats. He is nice, sociable and eats well. Do not miss the marinated kid cooked on the grill on the berbecue of the boat. Thank you Leo.
Nurit R.

Nurit R.

review about Walking around the Cyclades - Exclusive boat June 2022

10 / 10
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!
Victoria M.

Victoria M.

review about South of Lefkas between pristine nature bays of Meganisi and myths of Ithaca July 2021

10 / 10
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!
Patrick P.

Patrick P.

review about ALL INCLUSIVE crewed sailing holidays between Nafplion & Poros, both near Athens July 2019

10 / 10
An extraordinary week sailing with Christopher and Marie Nice welcome extra swimming course in beautiful coves Good music in the evening and delicious meal What a good time Adam and Allan took their first sailing course with Captain Christopher Do not hesitate to embark Thank you a thousand times Adam Allan Zena and Patrick

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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.

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