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Yacht sailing holidays & skippered tours in Italy

Discover more than 46 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!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

3 departures available

October

Starting from

€220

€187

Per person

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5.0

Super!

Blu Pontino - Evasione infrasettimanale

Italy: Pontine Islands

4 days - 3 nights

One departure available

October

Starting from

€180

Per person

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4.9

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

October - November

Starting from

€530

€477

Per person

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4.8

Super!

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

2 departures available

October

Starting from

€850

€808

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

October

Starting from

€294

Per person

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4.6

Premium

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

Italy: Northern Sardinia

7 days - 7 nights

4 departures available

October - November

Starting from

€1,455

€1,382

Per person

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5.0

Between seas and volcanoes, fall in love with the Aeolian Islands

Italy: Aeolian Islands

5 days - 4 nights

2 departures available

October

€590

Per person

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5.0

Super!

Weekend di emozioni nel Blu Pontino

Italy: Pontine Islands

3 days - 2 nights

One departure available

October - November

€180

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

October

Starting from

€615

Per person

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4.2

Stuffed anchovies: magical weekend from Genoa

Italy: Liguria

2 days - 2 nights

2 departures available

October

€265

Per person

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4.8

Midweek special on the island of Elba, 2 nights

Italy: Tuscany

3 days - 2 nights

One departure available

September - October

Starting from

€260

€247

Per person

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5.0

Super!

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Italy: Lake Garda

1 day - 0 nights

One departure available

September

Starting from

€99

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

12322 reviews

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Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

06/14/2025

Linda H.

-

Australia

It was an amazing experience exceeded my expectations. The all female crew were excellent They went over and above their duties. They were very caring respectful and tried to make our experience a positive enjoyable experience which they did perfectly. It was one of the best Sailing trips I have ever done.
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Life-changing experiences: Four days in the Pontine Islands

06/13/2025

Cristiano P.

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Italy

Fantastico. Esperienza meravigliosa. Divertente, bella, ho solo aggettivi positivi
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Weekend at the Pontine a stone's throw from Rome

06/12/2025

armando a.

-

Switzerland

È stata una bellissima esperienza con Antonio! Posti fantastici! Sarebbe stato ancora più bello navigare solo con le vele ma purtroppo le condizioni meteo e dell' equipaggio non lo permettevano. Da rifare sicuramente ;)
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Weekend at the Pontine a stone's throw from Rome

06/12/2025

Daniela B.

-

Italy

Una barca d’epoca curata e amata, uno skipper di esperienza con competenze e grandi doti da intrattenitore (anche ottimo cuoco), un equipaggio piacevole e rispettoso e isole che ti rubano il cuore. Questo in sintesi il nostro we con Antonio e la sua barca, ma non possiamo ridurre a poche righe il nostro weekend. Antonio è un vero “lupo di mare” e grazie alle sue competenze ci ha raccontato storie di mare, di uomini, di isole, di uccelli migratori, di palme e di antichi romani. Le sue capacità come restauratore di barche d’epoca si apprezzano vivendo sulla sua barca che mantiene immutato il fascino di un tempo. Abbiamo visitato calette e grotte accompagnate dallo skipper che con il tender ci ha portato dove la comoda barca da 15m non poteva arrivare, dormito in rada e veleggiato quando il tempo lo consentiva. Un’esperienza da ripetere che ci ha rapito il cuore.

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