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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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4.9

Super!

Easter on the Island of Elba

Italy: Tuscany

3 days - 3 nights

One departure available

April

€278

Per person

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4.9

Super!

May Day between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

April - May

€280

Per person

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4.8

Super!

Capri Light Blue, thermal Ischia and colorful Procida

Italy: Naples & Amalfi Coast

4 days - 3 nights

One departure available

April - May

€373

€317

Per person

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4.9

Super!

A weekend of sailing in Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

April

€220

Per person

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4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

3 departures available

April

Starting from

€275

Per person

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4.7

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

4 departures available

April

Starting from

€200

€180

Per person

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4.9

Four days exclusively on Elba between aperitifs and sailing

Italy: Tuscany

4 days - 3 nights

4 departures available

April

Starting from

€250

Per person

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

Italy: Aegadian islands

2 days - 2 nights

One departure available

April

€470

Per person

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5.0

Sea, sailing and relaxation in the beautiful Aeolian archipelago

Italy: Aeolian Islands

4 days - 4 nights

One departure available

April - May

Starting from

€400

Per person

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4.8

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

4 departures available

April - May

Starting from

€500

Per person

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5.0

Weekend only four guests - Elba Island

Italy: Tuscany

2 days - 2 nights

One departure available

April

Starting from

€260

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

4 departures available

April - May

Starting from

€650

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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