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Yacht sailing holidays & skippered tours in Italy

Discover more than 238 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

238

experiences

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4.3

Seven days on a sailing boat (14 meters) between Pontine and Flegree

Duration:

6 days - 6 nights

Italy:

Pontine Islands

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+6 travellers

have booked

€790

Per person

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4.9

Capraia under full sail / trekking on the island

Duration:

3 days - 2 nights

Italy:

Tuscany

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+4 travellers

have booked

€299

Per person

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4.3

Weekend on a 14-metre sailing yacht with skipper

Duration:

3 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

€410

Per person

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4.9

Life Changing Experiences - Isole Pontine

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+8 travellers

have booked

€420

Per person

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5.0

Weekend at the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

€462

Per person

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4.9

Weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+15 travellers

have booked

€362

Per person

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5.0

Relaxing weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+42 travellers

have booked

€415

Per person

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5.0

Relaxing weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

Starting from

€330

Per person

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4.9

Sailing weekend in Ponza and Palmarola!

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+30 travellers

have booked

€351

€390

Per person

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4.9

Sailboat Trip and Aperitif in the Gulf of Tigullio - All inclusive!

Duration:

1 day - 0 nights

Italy:

Liguria

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+58 travellers

have booked

Starting from

€85

Per person

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4.8

Sailing weekend in the Pontine Islands

Duration:

2 days - 2 nights

Italy:

Pontine Islands

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+8 travellers

have booked

€450

Per person

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4.8

Capri Light-Blue, Positano blu-sky, Amalfi history-dreams

Duration:

3 days - 2 nights

Italy:

Amalfi Coast

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+15 travellers

have booked

€333

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 - Yacht sailing holidays & skippered tours in Italy

10913 reviews

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Weekend in Capraia, the island with timeless sunsets

05/7/2024

Irene T.

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Italy

Marco è un gran marinaio, super esperienza!
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Week End Basic and Advanced Sailing Course

05/7/2024

Federico B.

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Italy

Skipper molto preparato, ha messo tutti a proprio agio. Barca confortevole, una giusta via di mezzo tra creciera e regata. Comoda e spaziosa per la crociera ma anche con la possibilità di molte regolazioni più caratteristiche della regata. Esperienza positiva! Assolutamente da ripetere!
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1st May - Whale watching cruise with WWF researcher between Elba and Capraia

05/6/2024

Elettra B.

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Italy

Esperienza ottima. Immersione totale nella vita da barca con una parte di spiegazioni sulla vita del mare e dei nostri stupendi mammiferi marini. Organizzato con cura, attenzione e andando incontro ai bisogni delle persone presente dove possibile. Barca stupenda, tenuta bene, cibo in abbondanza, persone speciali con cui condividere spazi e tempo. Silvia molto attenta, veloce e simpatica, con una conoscenza approfondita della vita marina e non solo che trasmette senza fatica. Giulia super preparata e ottima relatrice. Anche se il tempo ci è stato avverso è stata un'esperienza unica di cui sono molto soddisfatta. Consigliata. Il capitano della vela è stato il top. Elettra .
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Catamaran weekend: La Spezia, Portovevere, Lerici and Cinque Terre

05/6/2024

Paola d.

-

Italy

Esperienza superpositiva. Catamarano comodissimo e nuovissimo.. Molto gradita la prenotazione delle cene a terra da parte dello skipper Maurizio sempre disponibile e discreto. Grazie 😀

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