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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.

282

experiences

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Sailing day Genoa, Camogli and San Fruttuoso

Duration:

1 day - 0 nights

Italy:

Liguria

Be the first one to book!

Starting from

€110

Per person

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5.0

Sail with lunch on board

Duration:

1 day - 0 nights

Italy:

Lazio

Be the first one to book!

€89

Per person

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4.9

Trekking & Sailing Experience-Weekend lungo a Capraia, 2 barche

Duration:

3 days - 3 nights

Italy:

Tuscany

Be the first one to book!

Starting from

€295

€310

Per person

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4.9

Weekend on Elba between Sailing and Trekking

Duration:

2 days - 2 nights

Italy:

Tuscany

Be the first one to book!

Starting from

€280

Per person

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4.9

Between Western Liguria and Côte d'Azur from Imperia - Stewardess on board

Duration:

2 days - 2 nights

Italy:

Liguria

Be the first one to book!

€190

Per person

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A weekend in Liguria between Genoa and Portofino

Duration:

2 days - 2 nights

Italy:

Liguria

Be the first one to book!

Starting from

€180

€200

Per person

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5.0

Sailing day in the Ligurian nature, boarding from Varazze

Duration:

1 day - 0 nights

Italy:

Liguria

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chiara c.

Has booked

€95

Per person

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4.9

SUSHI SU UNA LUSSUOSA BARCA A VELA

Duration:

1 day - 0 nights

Italy:

Lazio

Be the first one to book!

€70

Per person

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The Aeolian Islands in an exclusive boat

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

Be the first one to book!

Starting from

€500

Per person

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4.8

An unforgettable sail to discover the Egadi Islands

Duration:

3 days - 4 nights

Italy:

Aegadian islands

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+14 travellers

Have booked

Starting from

€298

€350

Per person

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5.0

Trekking weekend on the Island of Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

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+12 travellers

Have booked

Starting from

€228

€240

Per person

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4.9

Trekking and sailing weekend on the island of Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

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+4 travellers

Have booked

Starting from

€228

€240

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.

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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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