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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.

401

experiences

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5.0

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+40 travellers

have booked

Starting from

€99

Per person

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Gulf of Poets, Portovenere, Palmaria and the island of Tino a Vela

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€120

Per person

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5.0

A day sailing in the fantastic Gulf of Trieste

Duration:

1 day - 0 nights

Italy:

Venice and the Gulf of Trieste

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+4 travellers

have booked

Starting from

€85

Per person

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4.9

Sailing excursion to Capri / Positano

Duration:

1 day - 0 nights

Italy:

Gulf of Naples

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+2 travellers

have booked

€160

Per person

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5.0

Veleggiata verso il farò di Cecina con Aperitivo a bordo

Duration:

1 day - 0 nights

Italy:

Tuscany

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+2 travellers

have booked

€55

Per person

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Magic charter Sorrento Capri Amalfi Positano

Duration:

4 days - 3 nights

Italy:

Amalfi Coast

Give this experience a try!

€750

Per person

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5.0

Venice and the Venetian Lagoon

Duration:

2 days - 2 nights

Italy:

Venice and the Gulf of Trieste

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+4 travellers

have booked

€188

Per person

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5.0

Aeolian Islands in serenity. Boat with 3 cabins and 3 bathrooms

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€433

Per person

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5.0

Sea, sailing and relaxation in the beautiful Aeolian archipelago

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€333

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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5.0

All inclusive day trip sailing around the Golfo Paradiso - flex dates

Duration:

1 day - 0 nights

Italy:

Liguria

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+12 travellers

have booked

Starting from

€126

€140

Per person

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Smart Working on a Sailing Boat: Adriatica is waiting for you on board!

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

€299

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

112 reviews

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Easter on the Island of Elba

04/22/2024

Antonios S.

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Italy

Anche se il tempo non ha aiutato, è stata una bellissima esperienza
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Trekking and sailing weekend on the island of Elba

04/22/2024

Sara C.

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Italy

Bellissima esperienza,grazie alla cordialità e professionalità di Marco e i compagni di avventura. Ho apprezzato molto anche la possibilità di fare trekking. Consigliatissimo!!
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Veleggiata verso il farò di Cecina con Aperitivo a bordo

04/11/2024

maurizio r.

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Italy

Grazie per la bella domenica di relax in barca Maurizio e Giuliana
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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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