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Hire a whole boat with skipper in the Aeolian Islands

Hire a whole boat with skipper in the Aeolian Islands

Discover the magic of sailing holidays in the Aeolian Islands! Hire a whole boat: a new way of traveling with your loved one, your friends or your family. Find your dream adventure among thousands of holidays from the Mediterranean to the Caribbeans.

  • Sailing Holidays
  • Italy
  • Aeolian Islands
  • Whole boat with skipper

COVID‑19

Additional guarantees on reservations, free cancellation and payment in tranches.

  • 1 review

    Give yourself an experience aboard a "comfortable" sailboat in the Aeolian Islands

    from 24 April - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    542€ Per person
  • 4 reviews

    Distinti & Distanti - 3 Cabins and 3 Bathrooms - Recent boat - Professional skipper

    from 24 April - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    540€ Per person
  • 1 review

    Give yourself an experience aboard a "comfortable" sailboat in the Aeolian Islands

    from 1 May - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    542€ Per person
  • 4 reviews

    Distinct & Distant - 3 Cabins and 3 Bathrooms - Recent boat - Professional skipper

    from 1 May - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    540€ Per person
  • 1 review

    Give yourself an experience aboard a "comfortable" sailboat in the Aeolian Islands

    from 8 May - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    542€ Per person
  • 4 reviews

    “Distinct & Distant” - 3 Cabins and 3 Bathrooms - Recent boat - Expert skipper

    from 8 May - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    540€ Per person
  • 1 review

    Give yourself an experience aboard a "comfortable" sailboat in the Aeolian Islands

    from 15 May - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    542€ Per person
  • 4 reviews

    “Distinct & Distant” - 3 Cabins and 3 Bathrooms - Recent boat - Expert skipper

    from 15 May - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    540€ Per person
  • 4 reviews

    “Distinct & Distant” - 3 Cabins and 3 Bathrooms - Recent boat - Expert skipper

    from 22 May - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    560€ Per person
  • confirmed

    May in the Aeolian Islands - the best time to sail between the islands!

    from 22 May - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    893€ Per person
  • 1 review

    Give yourself an experience aboard a "comfortable" sailboat in the Aeolian Islands

    from 22 May - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    542€ Per person
  • 45 reviews
    confirmed

    Sailing towards the Aeolian Islands

    from 25 May - 4 nights
    Aeolian Islands Italy
    Join in on this experience!
    231€ Per person
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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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Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

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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 the Aeolian Islands

2 reviews
20 / 10
Daniele F.

Daniele F.

review about September weekend in the Aeolian Islands September 2019

10 / 10
I 2 giorni a bordo della barca di Andrea sono stati meravigliosi sia per me che per i miei 7 colleghi norvegesi. Grande conoscitore delle Eolie, aveva sempre pronte un paio di opzioni da proporci, a seconda delle condizioni meteo e dei nostri interessi. Non ci ha mai imposto niente, assecondando le nostre richieste, e dandoci comunque suggerimenti preziosi sui migliori ristoranti o su dove trovare la migliore granita dell'arcipelago. A bordo e' sempre stato gentile, disponibile, chiacchierone e pronto a dare spiegazioni se qualcosa non era chiaro. Ci ha preparato il caffe' a colazione e anche cucinato il pesce al bbq! In 2 parole, Andrea e' stato fondamentale x la felice riuscita del nostro weekend!
Vanessa C.

Vanessa C.

review about Aeolian Islands in freedom and relax May 2019

10 / 10
Super séjour, un skipper très attentionné et vraiment sympathique, de très bon souvenirs, merci pour tout Mario !
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