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Hire a whole boat with skipper in Tuscany

Hire a whole boat with skipper in Tuscany

Discover the magic of sailing holidays in the Aeolian Islands! Get onboard with a local skipper and live a unique adventure with your crew: learn to sail, explore incredible places, recharge your batteries and experience the local culture & gastronomy.

  • Sailing Holidays
  • Italy
  • Tuscany
  • Whole boat with skipper

COVID‑19

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

  • 68 reviews

    Sailing and trekking weekend in Capraia

    from 23 April - 2 nights
    Tuscany Italy
    Join in on this experience!
    189€ Per person
  • 7 reviews

    Towards Elba, Corsica and Capraia - Hostess on board

    from 23 April - 2 nights
    Tuscany Italy
    Join in on this experience!
    252€ Per person
  • 26 reviews

    First miles on a sailing boat

    from 23 April - 2 nights
    Tuscany Italy
    1 person interested
    in this holiday
    105€ Per person
  • 34 reviews

    The queen of the Tuscan archipelago "Elba Island"

    from 23 April - 2 nights
    Tuscany Italy
    1 person interested
    in this holiday
    199€ Per person
  • Weekend sailing in the Tuscan Archipelago

    from 23 April - 2 nights
    Tuscany Italy
    Join in on this experience!
    221€ Per person
  • 36 reviews

    April, colors, scents and the sea of Elba

    from 24 April - One night
    Tuscany Italy
    Join in on this experience!
    158€ Per person
  • 34 reviews

    Fairytale May Day on the island of Elba

    from 30 April - 2 nights
    Tuscany Italy
    Join in on this experience!
    248€ Per person
  • 7 reviews
    confirmed

    Sailing towards Elba and Capraia.

    from 30 April - 2 nights
    Tuscany Italy
    Join in on this experience!
    263€ Per person
  • 68 reviews

    Sailing and trekking weekend in Capraia

    from 30 April - 2 nights
    Tuscany Italy
    2 people interested
    in this holiday
    189€ Per person
  • 29 reviews

    The caves of Capraia and its sunsets

    from 30 April - 2 nights
    Tuscany Italy
    Join in on this experience!
    191€ Per person
  • 62 reviews

    Cruise in the blue sea of Capraia

    from 30 April - 2 nights
    Tuscany Italy
    Join in on this experience!
    234€ Per person
  • 4 reviews
    2 discounted
    spots

    Sailing Week End on the wonderful Elba Island between nature and relaxation - Hostess on board

    from 30 April - 2 nights
    Tuscany Italy
    1 person interested
    in this holiday
    189 178€ Per person
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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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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 Tuscany

8 reviews
20 / 10
Eloise T.

Eloise T.

review about A week of pure relaxation, sea and strolls in the Tuscan Archipelago August 2020

10 / 10
Francesco è uno skipper molto professionale e preparato attento ai suoi ospiti e con una particolare dedizione per la cucina. Abbiamo passato una bellissima settimana in barca con i nostri bimbi e nonostante fosse la nostra prima esperienza ci siamo trovati molto a nostro agio e grazie alla passione per la vela che Francesco ci ha trasmesso siamo sicuri che ci saranno molte altre esperienze future. Super consigliato!
Marta S.

Marta S.

review about Tuscan Archipelago ... wait for us! An unforgettable sailing week between sport and fun! August 2020

10 / 10
Esperienza straordinaria ! Daniele uno skipper capace sempre tranquillo affiancato dal figlio Andrea un ragazzo disponibile e ben preparato. Pina ci ha letteralmente viziato con i suoi manicaretti . Hanno saputo creare un clima familiare. Provare per credere . Grazie
Maria Elena  P.

Maria Elena P.

review about Discovering the Gulf of Baratti July 2020

8 / 10
Abbiamo viaggiato con Massimo e Joshua, due skipper professionali e disponibili. Bellissima esperienza. Da rifare!
Mario S.

Mario S.

review about In search of DOLPHINS around the Island of Elba June 2020

10 / 10
È stata una vacanza breve (weekend) ma davvero indimenticabile, anche oltre le aspettative! Barca bellissima, tutta per noi (eravamo in sei), e tempo perfetto. Con due bambini piccoli abbiamo navigato a vela e anche in notturna, esperienza molto suggestiva. Un grande grazie a Salvo, skipper eccellente, per la sua disponibilità, competenza e attenzione alle nostre esigenze! Consigliatissimo!
Elena D.

Elena D.

review about Circumnavigation of the Island of Elba on a traditional aurica schooner in Tuscany August 2019

10 / 10
Abbiamo trascorso 6 gg su questa fantastica barca " ecologica" , in compagnia di Francesco e di suo figlio Alejandro, piacevoli compagni di viaggio. Stare su questa barca è un viaggio nel viaggio, ti riporta alla consapevolezza del mondo in cui viviamo e come lo viviamo: consiglio a tutti di provare l' esperienza con mente e cuori aperti. Buon viaggio!
Roberta M.

Roberta M.

review about These places in front of the sea 2019 July 2019

10 / 10
Gianpaolo è un ottimo skipper, navigare con lui dà sicurezza. Fa rispettare le regole , ma con gentilezza. Riesce a essere presente, ma mai invadente. È di compagnia, chiacchiera volentieri , e ci ha portato in posti molto belli. Bella e spaziosa la barca, Insomma. Se cercate uno skipper in gamba , e una vacanza divertente e/o tranquilla , Gianpaolo fa al caso vostro.
Francesca A.

Francesca A.

review about The company of new friends ... priceless! June 2019

10 / 10
Che dire! Bellissima esperienza di vela alla scoperta del mare incontaminato dell'Isola di Capraia! Claudio e Nori sono persone che non si incontrano facilmente nella vita: solari, disponibili,ti mettono subito a tuo agio e ti fanno sentire dei veri "pirati"...alla conquista del mare! Week end perfetto ( Eolo poteva fare di più ma non ci lamentiamo)...siamo rimasti colpiti anche dalla bravura dello Chef Claudio, che ci ha coccolato con deliziose specialità! Tutto perfetto...peccato che il week end vola via! Grazie ...speriamo a presto! Buon Vento!
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