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Yacht sailing holidays & skippered tours in Italy

Discover more than 11 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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4.9

Super!

Sailing course for beginners

Italy: Liguria

2 days - 1 night

4 departures available

January - February

Starting from

€270

Per person

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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

4 departures available

January

€190

Per person

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4.7

Experience the Befana as you have never seen it before... by boat!

Italy: Tuscany

4 days - 4 nights

One departure available

January

€270

€243

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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4.8

New Year's Eve on Elba on two boats: sequins in the dinette!

Italy: Tuscany

3 days - 2 nights

One departure available

December - January

€250

Per person

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4.9

New Year's Eve with friends in the Gulf of Naples

Italy: Naples & Amalfi Coast

5 days - 5 nights

One departure available

December - January

€550

Per person

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5.0

We take a breath carried by the wind: we discover the sea in winter

Italy: Liguria

2 days - 1 night

4 departures available

January - February

Starting from

€250

Per person

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5.0

New Year's Eve on a sailing boat with dinner on board

Italy: Tuscany

3 days - 2 nights

One departure available

December - January

€500

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

January

€580

Per person

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5.0

A day of sailing out of season!

Italy: Tuscany

1 day - 0 nights

4 departures available

January

€100

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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Weekend on Elba "Only for four" for maximum comfort

11/25/2025

D. D.

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Italy

Great weekend! Impeccable welcome on Friday evening, really much appreciated. Very professional and prepared skipper (also the other crew members) - experienced hands-on in the challenging (but fun) crossing. I learned a lot (main objective - achieved). I hope to have the chance of another experience together soon.
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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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