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Yacht sailing holidays & skippered tours in Italy

Discover more than 240 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

240

experiences

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Eolie a vela con skipper ed hostess, all inclusive con cucina vegana

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+2 travellers

have booked

Starting from

€1,500

Per person

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4.8

Week in Southern Sardinia - Science of Happiness on board

Duration:

6 days - 7 nights

Italy:

Southern Sardinia

Give this experience a try!

€711

€790

Per person

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4.8

Egadi Islands - Sea, sun, relax on a brand new catamaran 2024

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+5 travellers

have booked

Starting from

€899

Per person

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5.0

EOLIE IN RELAX - Boat with 3 cabins and 3 bathrooms

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+6 travellers

have booked

Starting from

€550

Per person

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4.5

Sailing holiday with maximum comfort

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+6 travellers

have booked

Starting from

€360

Per person

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4.9

In the blue between Sardinia and Corsica on a sailboat

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+114 travellers

have booked

€650

Per person

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4.0

Magical Amalfi Coast, Capri, Ischia and Procida by Catamaran

Duration:

6 days - 7 nights

Italy:

Amalfi Coast

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+6 travellers

have booked

€1,250

Per person

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4.8

Discover the magic of the Pontine Islands

Duration:

6 days - 7 nights

Italy:

Pontine Islands

Give this experience a try!

€616

Per person

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4.8

Aeolian Islands: wellness, taste and fun

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+12 travellers

have booked

Starting from

€580

Per person

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4.9

The Maddalena Archipelago by sail.

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+35 travellers

have booked

Starting from

€650

Per person

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3.5

Egadi Islands, Zingaro Nature Reserve, San Vito lo Capo

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+3 travellers

have booked

€585

€650

Per person

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A week in the pristine waters of Lampedusa, Linosa and Lampione

Duration:

6 days - 7 nights

Italy:

Pantelleria and Lampedusa

Give this experience a try!

€800

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

10916 reviews

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Weekend with wine tasting between Santa Margherita Ligure and Portofino

05/7/2024

Valentina B.

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Italy

Siamo stati fortunati ad avere Giorgio come skipper durante il nostro weekend in barca a vela. La sua gentilezza e professionalità hanno reso l'intero viaggio un’esperienza straordinaria. Giorgio ha mostrato una grande attenzione per la sicurezza e il comfort a bordo. La sua personalità amichevole e la sua capacità di mettere a proprio agio le persone hanno reso il viaggio ancora più piacevole. Giorgio è stato un ottimo skipper ma anche un provetto chef: grazie alla conoscenza dei vini e alla passione per la cucina ha creato un aperitivo stuzzicante e una cena, a base di pesce, davvero deliziosa. La barca è molto bella, confortevole e pulita. Consiglio vivamente Giorgio a chiunque cerchi un'esperienza di vela emozionante, in un contesto amichevole.
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Week End Basic and Advanced Sailing Course

05/7/2024

Antonio R.

-

Italy

Bellissima esperienza!!assolutamente da ripetere!!
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Weekend in Capraia, the island with timeless sunsets

05/7/2024

enrico g.

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Italy

ottimi compagni di viaggio , marco m disponibilissimo e molto preparato grazie a tutti
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Weekend in Capraia, the island with timeless sunsets

05/7/2024

Irene T.

-

Italy

Marco è un gran marinaio, super esperienza!

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