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Hire a whole boat with skipper in Greece

Hire a whole boat 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

COVID‑19

Book without stress paying a small deposit, cancellation is free!.

  • 2 reviews

    A fantastic holiday aboard the Sponge Bob Catamaran along the ancient routes of Ulysses

    from 10 April - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    1.292€ Per person
  • 4 reviews
    6 discounted
    spots

    Combo itinerary: Saronic & Cyclades islands - Customised itinerary for private charter

    from 19 April - 6 nights
    Saronic Islands and Athens area Greece
    Join in on this experience!
    860 755€ Per person
  • 2 reviews
    5 discounted
    spots

    Mykonos & Paros through Naxos, Small Cyclades, Syros and Tinos . The BEST of the Cyclades

    from 19 April - 6 nights
    Cyclades Greece
    Join in on this experience!
    794 741€ Per person
  • 9 reviews

    10 days from Athens to Santorini via Milos and Folegandros

    from 20 April - 9 nights
    Cyclades Greece
    Join in on this experience!
    840€ Per person
  • Sailing in the footsteps of Ulysses! 7 days to discover the Ionian islands with hostess on board

    from 21 April - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    725€ Per person
  • 1 review

    Discover the North Sporades with local Skipper!

    from 24 April - 7 nights
    Sporades Greece
    Join in on this experience!
    531€ Per person
  • 8 reviews
    2 discounted
    spots

    Are you a lover of nature and crystalline seas? Join us: zero stress and HOSTESS ON BOARD!

    from 24 April - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    462 425€ Per person
  • 31 reviews

    The holidays of April 25th and May 1st in the Cyclades

    from 24 April - 11 nights
    Cyclades Greece
    Join in on this experience!
    849€ Per person
  • Sporades Islands: sailing holidays are more than just holidays!

    from 24 April - 7 nights
    Sporades Greece
    Join in on this experience!
    662€ Per person
  • 2 discounted
    spots

    Stroll around the Dodecanese on a 15m boat - boarding in Kos or Leros

    from 24 April - 7 nights
    Dodecanese Greece
    Join in on this experience!
    452 427€ Per person
  • 2 reviews

    An incredible journey sailing among the most enchanting islands of Greece

    from 24 April - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    750€ Per person
  • 14 reviews

    The enchantment of the sea: from Corfu to Athens through the Corinth Canal

    from 24 April - 7 nights
    Ionian Islands Greece
    2 people interested
    in this holiday
    301€ Per person
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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 - Hire a whole boat with skipper in Greece

1 review
20 / 10
Patrick P.

Patrick P.

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

10 / 10
Une semaine extraordinaire en voilier avec Christopher et Marie Accueil sympa parcours extra baignade dans de superbes criques Bonne musique le soir et repas délicieux Que du bon temps Adam et Allan pris leur premier cours de navigation avec le captain Christopher N’hésitez pas à embarquer Merci mille fois Adam Allan Zena et 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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