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Yacht sailing holidays & skippered tours in Italy

Discover more than 72 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!

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!

The gems of the Amalfi Coast: Capri Light Blue, Positano Blue Sky, Amalfi Dreaming History

Italy: Naples & Amalfi Coast

4 days - 3 nights

One departure available

April

Starting from

€320

Per person

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5.0

Super!

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

11 departures available

April

Starting from

€59

Per person

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5.0

Super!

Spring at the Pontine

Italy: Pontine Islands

4 days - 3 nights

One departure available

April

€400

Per person

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5.0

Super!

Weekend del Garda

Italy: Lake Garda

2 days - 2 nights

One departure available

April - May

€179

Per person

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5.0

Super!

1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK

Italy: Tuscany

3 days - 3 nights

One departure available

April - May

€430

€409

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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5.0

Super!

Discovering Elba... and maybe even Capraia!

Italy: Tuscany

3 days - 3 nights

5 departures available

April - May

€390

€351

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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4.9

Super!

Family Campus on a sailing boat in the Cinque Terre

Italy: Liguria

2 days - 2 nights

One departure available

April

€380

Per person

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5.0

Super!

Vulcano Island (Aeolian Islands): from sea caves to volcanic crater

Italy: Aeolian Islands

2 days - 1 night

2 departures available

April

€260

€234

Per person

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4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

One departure available

April

€275

Per person

Why book a holiday with Sailsquare?

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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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