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Sailboat yacht sailing holidays & tours in Italy

Discover more than 352 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

352

experiences

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4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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62 travellers

€990

€1,190

Per person

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5.0

Super!

May Day long weekend to discover the islands of Elba and Capraia

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€380

€460

Per person

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5.0

Super!

Settimana in barca a vela tra Toscana e Corsica

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€1,275

€1,500

Per person

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Escape to the Magical Blue of the Pontine Islands

Duration:

4 days - 3 nights

Italy:

Pontine Islands

Give this experience a try!

€353

€415

Per person

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4.8

Super!

Lampedusa, Lampione e Linosa fra colori magici

Duration:

7 days - 7 nights

Italy:

Pantelleria and Lampedusa

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34 travellers

€595

€700

Per person

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4.7

Two boats walking on the island of Elba: the magic of the roadstead!

Duration:

6 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€638

€750

Per person

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4.6

Cruise to the Maddalena Archipelago and South Corsica

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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28 travellers

Starting from

€667

€785

Per person

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5.0

Poetic Gulf of Poets

Duration:

3 days - 2 nights

Italy:

Liguria

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12 travellers

Starting from

€170

€200

Per person

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4.5

May Day on a Sailing Boat between Procida, Ischia and Ventotene

Duration:

4 days - 4 nights

Italy:

Pontine Islands

Give this experience a try!

€378

€420

Per person

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4.9

Super!

Long weekend on Elba: 4 days of sun and sailing

Duration:

3 days - 3 nights

Italy:

Tuscany

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17 travellers

Starting from

€342

€380

Per person

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4.3

Sailing holiday in the archipelago of La Maddalena and Costa Smeralda

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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2 travellers

Starting from

€720

€800

Per person

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4.0

15 days wandering in the southern Tyrrhenian Sea

Duration:

15 days - 15 nights

Italy:

Aeolian Islands

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2 travellers

€1,755

€1,950

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 - Sailboat yacht sailing holidays & tours in Italy

11215 reviews

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First spring getaways in the company of the sea

04/29/2025

Raffaella Valeria R.

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Italy

Esperienza in barca vela TOP!!! Carlo è uno skypper super preparato, professionale, attento ad ogni dettaglio e capace di trasmettere tutta la sua passione e conoscenza del mare e della vela con gentilezza. Partecipare attivamente alle manovre e alle analisi meteo ti fa vivere al 100% l'andare in vela. Grazie Carlo!
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25 April long weekend between Capraia and Northern Corsica

04/29/2025

VERONICA D.

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Italy

Un esperienza meravigliosa. Complimenti al capitano, bravissimo nel creare gruppo e un ottimo amico di bordo. A presto Francesco
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Day trip with aperitif at sunset!

04/28/2025

Silvia Maddalena V.

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Italy

Bellissima giornata in ottima compagnia!
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25 April long weekend between Capraia and Northern Corsica

04/28/2025

Luigi C.

-

Italy

Bellissimo weekend all'insegna del sole, del mare, della vela e della buona compagnia. Le mete della destinazione sono stupende, la barca é comodissima e Francesco é uno skipper esperto sempre attento alle esigenze dell'equipaggio. Ottimo cuoco, grande appassionato di vela e persona gradevolissima, ci ha fatto sentire a casa insegnandoci allo stesso tempo tante nozioni sulla vela, con passione e simpatia. Torneremo sicuramente a trovarlo!

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