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Yacht sailing holidays & skippered tours in Italy

Discover more than 131 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

131

experiences

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4.6

North Sardinia - La Maddalena and Costa Smeralda

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+16 travellers

have booked

Starting from

€600

Per person

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5.0

An all-inclusive day on a sailing boat

Duration:

1 day - 0 nights

Italy:

Liguria

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+14 travellers

have booked

€180

Per person

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4.8

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms plus crew

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+27 travellers

have booked

Starting from

€650

Per person

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4.8

Whale watching cruise with WWF in Liguria between Portofino and Cinque Terre

Duration:

5 days - 6 nights

Italy:

Liguria

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+25 travellers

have booked

€749

Per person

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4.8

Whale watching cruise with WWF researcher on 18-meter schooner

Duration:

6 days - 6 nights

Italy:

Tuscany

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+10 travellers

have booked

€979

Per person

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5.0

Cruise between Elba, Corsica Del Nord and Capraia with PROFESSIONAL SKIPPER AND COOK

Duration:

6 days - 7 nights

Italy:

Tuscany

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+30 travellers

have booked

€713

€750

Per person

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4.8

Whale watching cruise with WWF researcher between the Tuscan Archipelago and Northern Corsica

Duration:

6 days - 6 nights

Italy:

Tuscany

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+5 travellers

have booked

Starting from

€889

Per person

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4.9

A week of sea, nature and fun in the Pontine Islands!

Duration:

6 days - 7 nights

Italy:

Pontine Islands

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+13 travellers

have booked

€690

Per person

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4.5

The Aeolian Islands as you've never seen them before

Duration:

4 days - 3 nights

Italy:

Aeolian Islands

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+8 travellers

have booked

Starting from

€380

Per person

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The secrets of the Aeolian Islands

Duration:

5 days - 5 nights

Italy:

Aeolian Islands

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+2 travellers

have booked

Starting from

€750

Per person

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5.0

Elba, Corsica and Capraia sailing

Duration:

6 days - 6 nights

Italy:

Tuscany

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+9 travellers

have booked

€630

Per person

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4.9

Weeks on a sailing boat in the Tuscan Archipelago: Elba Capraia Giglio

Duration:

7 days - 6 nights

Italy:

Tuscany

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+20 travellers

have booked

€625

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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