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Private yacht sailing holidays with skipper in the Ionian Islands

Private yacht sailing holidays with skipper in the Ionian Islands

Who has never dreamed of hiring a sailboat and following Ulysses' routes? In the Ionian Islands you can choose between a sailboat, a catamaran or a gulet and sail to Zante, Ithaca, Corfu, Lefkada, Kastos.

  • Sailing Holidays
  • Greece
  • Ionian Islands
  • Whole boat with skipper

FLEXIBLE CANCELLATION.

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

  • 2 reviews
    almost
    confirmed

    Sailing cruise: Corfu, Paxos and Antipaxos

    from 20 August - 7 nights
    Ionian Islands Greece
    1 person interested
    in this holiday
    848€ Per person
  • 8 reviews
    almost
    confirmed

    Are you a lover of nature and crystalline seas? This is the perfect relaxing holiday

    from 20 August - 7 nights
    Ionian Islands Greece
    13 people interested
    in this holiday
    610€ Per person
  • 5 reviews
    4 discounted
    spots

    Sailing week Ionian Greece

    from 21 August - 7 nights
    Ionian Islands Greece
    1 person interested
    in this holiday
    1.103 1.050€ Per person
  • confirmed
    whole boat only

    We explore the Ionian islands aboard a Bavaria 46

    from 27 August - 7 nights
    Ionian Islands Greece
    Reserve this boat!
    (9 spots available)
    681€ Per person
  • 5 reviews
    1 discounted
    spot

    The Greece of the myth on a sailing boat

    from 27 August - 7 nights
    Ionian Islands Greece
    6 people interested
    in this holiday
    636 604€ Per person
  • 13 reviews
    4 discounted
    spots

    Exploring Ionian Greece and Salento - Hostess on board - Embarkation and disembarkation in LEUCA

    from 27 August - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    636 604€ Per person
  • 16 reviews
    confirmed

    Crossing from Lefkada to Split via Montenegro

    from 27 August - 7 nights
    Ionian Islands Greece
    5 people interested
    in this holiday
    610€ Per person
  • 1 review
    almost
    confirmed

    Corfu - Paxos - Anti Paxos - Parga

    from 29 August - 6 nights
    Ionian Islands Greece
    Join in on this experience!
    848 827€ Per person
  • 15 reviews

    In Galleon in the sea of Ulysses

    from 31 August - 7 nights
    Ionian Islands Greece
    3 people interested
    in this holiday
    879€ Per person
  • confirmed
    whole boat only

    We explore the Ionian islands aboard a Bavaria 46

    from 3 September - 7 nights
    Ionian Islands Greece
    Reserve this boat!
    (9 spots available)
    681€ Per person
  • 32 reviews
    almost
    confirmed

    South of Lefkas between pristine nature bays of Meganisi and myths of Ithaca

    from 3 September - 7 nights
    Ionian Islands Greece
    1 person interested
    in this holiday
    636€ Per person
  • 5 reviews
    4 discounted
    spots

    Sailing week Ionian Greece

    from 5 September - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    945 892€ Per person
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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 the Ionian Islands

1 review
20 / 10
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!
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Top Destinations

  • Italy
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  • Northern Sardinia
  • Pontine Islands
  • Caribbean
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Top Travel Ideas

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  • Monohull
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  • Sport & wellness
  • Whole boat with skipper
  • All inclusive
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  • WWF Sailing Cruises
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