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Yacht sailing holidays & skippered tours in Italy

Discover more than 15 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

One departure available

February - March

€270

Per person

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4.9

Super!

A weekend of sailing in Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

March

€220

Per person

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4.7

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

4 departures available

March

Starting from

€200

€180

Per person

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4.9

Weekend in the Pontine Islands: Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

5 departures available

February - March

Starting from

€180

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

5 departures available

February - March

€250

Per person

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4.9

A weekend at sea!

Italy: Lazio

3 days - 2 nights

3 departures available

March

€300

Per person

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5.0

Weekend on a sailing boat: course & fun

Italy: Tuscany

2 days - 2 nights

One departure available

February - March

Starting from

€300

€270

Per person

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Garda sailing tour: private sailing tour

Italy: Lake Garda

1 day - 0 nights

One departure available

March

€77

Per person

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4.8

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

4 departures available

March

Starting from

€230

Per person

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4.7

Corso di vela RYA Day Skipper Pratical sailing

Italy: Tuscany

4 days - 4 nights

4 departures available

March

€1,400

Per person

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5.0

Weekend only four guests - Elba Island

Italy: Tuscany

2 days - 2 nights

2 departures available

March

Starting from

€260

Per person

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4.9

Leave everything towards the Island of Elba

Italy: Tuscany

2 days - 2 nights

5 departures available

February - March

Starting from

€220

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

13750 reviews

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Midweek special on the island of Elba, 2 nights

01/24/2026

Sara M.

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Italy

I left with my brother: there were 7 of us, plus Marco. It was our first boat experience and we couldn't ask for anything better! Marco was extremely kind, helpful and attentive to every detail. The combination of the boat excursion and the trekking on the island was simply fantastic, everything impeccably organized. In addition, there was also the opportunity to enjoy free time in total relaxation. I absolutely recommend this experience with Marco!
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Experience the Befana as you have never seen it before... by boat!

01/14/2026

federico b.

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Italy

Beautiful 4 relaxing days despite the adverse weather, the legendary Francesco solved with trips to beautiful and really interesting places, excellent crew immediately close-knit.
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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.

-

Italy

Everything worked out great, Paolo was super helpful!!!! Advice 100%

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