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Yacht sailing holidays & skippered tours in Italy

Discover more than 12 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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4.8

Super!

The sea and sailing in winter, 2 days on the island of Elba

Italy: Tuscany

2 days - 1 night

2 departures available

December

€190

Per person

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4.8

Super!

The sea and sailing in autumn: two days on Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

November - December

€190

Per person

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New Year's Eve in the Egadi Islands on a sailing boat - Comfort & All Inclusive

Italy: Aegadian islands

2 days - 2 nights

One departure available

December - January

€510

Per person

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5.0

NEW YEAR'S EVE in the Gulf of Naples & Amalfi Coast on a catamaran with hostess

Italy: Naples & Amalfi Coast

4 days - 4 nights

One departure available

December - January

€620

Per person

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Day Cruise- Tour Golfo Dei Poeti

Italy: Liguria

1 day - 0 nights

8 departures available

December

€86

Per person

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5.0

Magical weekend on Giglio Island

Italy: Tuscany

2 days - 2 nights

One departure available

November

Starting from

€220

€198

Per person

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Christmas Mini Cruise to the Egadi Islands - Comfort & All Inclusive

Italy: Aegadian islands

2 days - 2 nights

One departure available

December

€490

Per person

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4.2

Weekend of theoretical and practical course

Italy: Liguria

2 days - 1 night

One departure available

November

€250

Per person

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Week-end a Vela in Liguria

Italy: Liguria

3 days - 2 nights

4 departures available

November - December

€250

Per person

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5.0

The magic of winter on the Amalfi Coast with Hostess

Italy: Naples & Amalfi Coast

4 days - 4 nights

One departure available

December

€580

Per person

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4.9

Weekend of relaxation and fun from Genoa

Italy: Liguria

2 days - 2 nights

One departure available

November

€260

€247

Per person

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4.1

East Coast of Sicily From Taormina to Portopalo. Cook on board

Italy: Sicily

6 days - 7 nights

One departure available

November - December

Starting from

€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

13757 reviews

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A day sailing in the fantastic Gulf of Trieste

11/11/2025

Armin F.

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Italy

Everything worked out great, Paolo was super helpful!!!! Advice 100%
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Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/10/2025

giulia f.

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Italy

I participated in the weekend on a sailing boat organized for the Squid Festival and I couldn't ask for anything better! It was a wonderful experience, between sea, wind and excellent company. The crew was great: nice people and with a great desire to have fun. The skipper is super professional, but also helpful and attentive to let us experience sailing in a relaxed and fun way. I can't wait to get back on board for the next adventure! ⚓️🐙✨ Giulia, Eva and Martina
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Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/5/2025

Marco F.

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Switzerland

Matteo is a professional skipper and above all a pleasant person, who steers the boat and situations with lightness and experience. Luke [hidden] a well-maintained and decidedly comfortable and spacious boat. Nice opportunity and fantastic company / crew, not to be forgotten and to be seen again with pleasure in a next navigation, between sea aperitifs and laughter.
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LET'S GO TO TOTANI - Festival in Capria

11/5/2025

Marco D.

-

Italy

Unforgettable and fun experience, very prepared skipper who tamed a sea that was not exactly docile. The fishing competition is beautiful and suggestive.

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