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Private yacht sailing holidays with skipper in Italy

Chartering a sailing boat in Italy will let you discover a new way of travelling new way of travelling in complete freedom. Choose between a catamaran or a sailing boat and embark with an experienced skipper to discover Tuscany, Sicily, Tuscany, Sicily, Sardinia and many other destinations.

359

experiences

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5.0

Offshore Didactic Navigation between Liguria, Tuscany and northern Corsica

Duration:

8 days - 7 nights

Italy:

Tuscany

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+7 travellers

have booked

€811

Per person

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4.5

1 Week Professional Catamaran Training - Cagliari Sardinia

Duration:

7 days - 7 nights

Italy:

Southern Sardinia

Give this experience a try!

€1,320

Per person

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4.5

Sailing day Maddalena Archipelago

Duration:

1 day - 0 nights

Italy:

Northern Sardinia

Give this experience a try!

€125

Per person

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4.6

April 25 between the Tuscan islands and North Corsica.

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€350

Per person

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4.9

Sailing & adventure among the Egadi Islands

Duration:

5 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€450

Per person

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4.6

Long weekend of April 25 Egadi Islands

Duration:

4 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€345

Per person

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4.3

Wellness Cruise: Sailing and Yoga in Nature

Duration:

4 days - 5 nights

Italy:

Southern Sardinia

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+2 travellers

have booked

€600

Per person

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5.0

Trekking & Sailing Experience 25 Aprile tra Elba e Capraia - 2 barche

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€494

€520

Per person

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4.9

Trekking & Sailing Experience 25 Apr Elba Island and Capraia - 2 boats

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€494

€520

Per person

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4.2

Ponte del 25 Aprile in navigazione con rotta per la Capraia.

Duration:

4 days - 4 nights

Italy:

Tuscany

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Riccardo R.

has booked

€435

Per person

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5.0

Long weekend in Capraia and North Corsica

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€375

Per person

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5.0

First dives in the Egadi Islands

Duration:

3 days - 4 nights

Italy:

Aegadian islands

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+11 travellers

have booked

Starting from

€360

Per person

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 - Private yacht sailing holidays with skipper in Italy

109 reviews

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Between aperitif sunsets and sailings on the island of Elba

09/19/2023

Lorenzo M.

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Monaco

La nostra prima vacanza in barca a vela. La barca è perfetta, spaziosa e confortevole, con due bagni separati (skipper e ospiti). Luca il proprietario ha reso l'esperienza speciale, una persona eccezionale, cuoco straordinario e padrone di casa accogliente. Navigare tra Elba, Corsica e Capraia con lui è stato un autentico piacere. è stato come essere in barca con un amico di lunga data o uno zio. Nota per i futuri naviganti: è golossissimo (come noi) di gorgonzola! Esperienza super consigliata specialmente per chi è alla prima esperienza. Purtoppo non possiamo dire altrettanto di sailsquare, ad oggi non abbiamo ancora ricevuto documenti come ricevuta di pagamento o contratto di charter. Inoltre ad una richiesta di assistenza non siamo mai stati ricontattati.
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Aeolian Islands on a sailing boat, an exaggerated holiday!

09/11/2023

Alessandro B.

Rosario si è dimostrato molto disponibile e competente, conosce molto bene le Isole Eolie, e anche se abbiamo avuto un paio di giorni di meteo non buono siamo riusciti a fare quasi tutto quello che prevedeva il programma. Consiglio sicuramente un'esperienza in barca a vela con Rosario
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Fabulous Egadi Islands by catamaran with hostess on board

09/4/2023

Liliana T.

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Italy

Catamarano grande, spazioso e funzionale. Cibo ottimo. Nonostante il mal tempo siamo riusciti a vivere una bella settimana di mare. Un'atmosfera poco serena tra hostess e skipper non mi permette di mettere 5 stelle. Barca e skipper comunque consigliati
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Aeolian Islands on a sailing boat, an exaggerated holiday!

08/29/2023

Ilaria C.

-

Italy

Rosario è il migliore! La vacanza è stata stupenda grazie alla bellezza dei luoghi e alla simpatia e disponibilità di Rosario. Con la sua esperienza e il suo entusiasmo è stato il miglior skipper che potessimo chiedere. Torneremo!

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