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Crewed yacht sailing holidays & tours in Tuscany

Get on board on a crewed sailing holiday in Tuscany for the most relaxed time ever.

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Crewed yacht sailing holidays & tours in Tuscany

162 reviews

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Week of sailing and sea between the Tuscan Archipelago and Corsica with Hostess

06/29/2025

Johan A.

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Belgium

Delightful week of sailing with Paolo and Bianca around Elba and Capraia... I enjoyed the sincere Italian hospitality (and delicious food) on the well-equiped 'Serafino'. They really made an effort to accomodate for every guest's wishes and preferences. What a team... grazie mille!!!
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Week of sailing and sea between the Tuscan Archipelago and Corsica with Hostess

06/28/2025

Michela M.

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Italy

Settimana stupenda. Bianca e Paolo sono stati due ospiti eccezionali, preparati, gentili, divertenti. Professionali ma che sanno farti sentire a casa. La cucina di Bianca è stata squisita e lei sempre pronta a riadattarla in caso di esigenze particolari. Paolo ci ha portati alla scoperta di calette nascoste in un mare splendido tra Elba e Capraia, pronto ad insegnare a chiunque volesse provare la vela e di grande compagnia tra giri all’avventura con il sup, karaoke e giochi sotto le stelle. La Serafino è una super barca, non manca nulla, un bagno privato per cabina (rarità), dinette e pozzetto comodi e molto curati. Consiglio e straconsoglio questa esperienza con loro!
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Week of sailing and sea between the Tuscan Archipelago and Corsica with Hostess

06/23/2025

Salvatore Andrea C.

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Italy

Esperienza straordinaria vissuta in piacevole compagnia, un grazie particolare va a Paolo e a Bianca, che mi hanno coinvolto, destinazioni fantastiche e mare bellissimo, consiglio a tutti di provare l'esperienza.
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Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

06/18/2025

Giuseppe L.

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Italy

Ottimo skipper,molto disponibile,uno dei pochi che va a vela quando può,persona cordiale,unico suggerimento è che per questo viaggio bisognerebbe ritrovarsi in mattinata e partire subito il primo giorno senza aspettare il giorno dopo,2 giorni sono troppi pochi

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