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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.

32

experiences

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4.5

Isole Egadi, Riserva dello Zingaro, San Vito Lo Capo - Hostess a bordo

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€585

€650

Per person

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Spring in the Cinque Terre

Duration:

3 days - 2 nights

Italy:

Liguria

Give this experience a try!

€189

€210

Per person

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5.0

Route to the Egadi Islands: Wind, Flavors and Sea

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€585

€650

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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56 travellers

Starting from

€675

€750

Per person

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5.0

Aeolian Islands: between sea and authentic flavours

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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44 travellers

Starting from

€765

€850

Per person

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5.0

Super!

Weekend between Ponza and Palmarola Comfortable - max 4 people

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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11 travellers

Starting from

€379

€421

Per person

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5.0

Aeolian Islands - A week on a sailing boat with skipper and assistant

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€786

€873

Per person

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5.0

Island of Capraia sailing and wild nature

Duration:

4 days - 4 nights

Italy:

Tuscany

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2 travellers

€405

€450

Per person

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4.8

Super!

Aeolian Islands: sun, sport, music, good food... The rest is magic!

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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129 travellers

Starting from

€618

€650

Per person

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4.9

Super!

Weekend of relaxation and fun from Marina degli Aregai in Liguria

Duration:

2 days - 2 nights

Italy:

Liguria

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39 travellers

€285

€300

Per person

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4.9

WINE TASTING with sommelier on board

Duration:

1 day - 0 nights

Italy:

Lazio

Give this experience a try!

€80

Per person

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4.9

Aperitif at sunset on a sailboat at the Port of Ostia

Duration:

1 day - 0 nights

Italy:

Lazio

Give this experience a try!

€40

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

1228 reviews

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Capraia and Totani, let's go!

11/10/2024

Pablo C.

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Italy

Ci siamo trovati molto bene con Ivo: skipper professionale, cuoco provetto e persona gioviale con tanto da raccontare! La sua barca è in ottime condizioni e ben pulita. Torneremmo volentieri in barca con lui.
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Capraia and Totani, let's go!

11/4/2024

MATTEO R.

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Italy

Skipper molto esperto, preciso e disponibile. Ottimo cuoco e pescatore!! Molto attento (anche troppo) alla cura della sua barca e alla sicurezza dell’equipaggio. Qualche costo extra (cambusa a forfait e tesseramento asd) da mettere in conto, ma nel complesso, consigliato!!
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Magical weekend on Giglio Island

10/20/2024

Altamir T.

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Brazil

La gita in barca all'Isola del Giglio, nell'arcipelago toscano, ha superato ogni mia aspettativa. La barca a vela Luna Sul Mare è comoda e sicura. Ho una certa esperienza con le barche a vela e appena salito a bordo ho notato la cura del Capitano Saverio D'Andrea in ogni dettaglio per garantire il benessere. Tutte le attrezzature sulla barca funzionano bene e la pulizia è rigorosa. Il tour è iniziato presso l'accogliente porto turistico di Talamone. L'ancoraggio al Giglio era nella bellissima Cala dello Smeraldo, dove ho potuto godermi il bagno in mare. Il pernottamento è stato tranquillo nel dolce dondolio delle acque protette. Nella tappa successiva il capitano ci ha portato all'Argentario, dove ho potuto godermi un altro delizioso bagno a Cala Grande, prima di ritornare a Talamone. Saverio oltre a fornire un bellissimo itinerario ha saputo integrare e armonizzare la convivenza del gruppo, che è stata sempre piacevole.
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Magical Barcolana Weekend: the most famous regatta!

10/15/2024

Antonio S.

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Italy

Scoprire la Barcolana come turista e partecipante alla gara è stata un'esperienza straordinaria. La compagnia dell'equipaggio è stata positiva. Dormire in barca non è facile, ma indispensabile per gustare l'avventura della regata al massimo.

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