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Yacht sailing holidays & skippered tours in Italy

Discover more than 13 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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4.8

Super!

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

November

€299

Per person

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4.8

Super!

The sea and sailing in autumn: two days on Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

November

€190

Per person

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4.8

Super!

LET'S GO TO TOTANI - Festival in Capria

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€420

Per person

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4.8

Squid Festival: let's close the season on a high note! - on board a 17mt boat

Italy: Tuscany

2 days - 2 nights

One departure available

October - November

€300

Per person

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3.0

7 islands in comfort and convenience

Italy: Aeolian Islands

6 days - 6 nights

One departure available

November

Starting from

€600

Per person

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Day Cruise- Tour Golfo Dei Poeti

Italy: Liguria

1 day - 0 nights

18 departures available

October - November

€86

Per person

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A terrace overlooking the sea: a day to discover the Gulf of Naples

Italy: Naples & Amalfi Coast

1 day - 0 nights

3 departures available

October

Starting from

€110

€88

Per person

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Daily sailing trip off the coast of beautiful Pisa

Italy: Tuscany

1 day - 0 nights

7 departures available

October - November

Starting from

€115

Per person

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4.2

Weekend of theoretical and practical course

Italy: Liguria

2 days - 1 night

5 departures available

November

€250

Per person

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Week-end a Vela in Liguria

Italy: Liguria

3 days - 2 nights

5 departures available

October - November

€250

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

One departure available

November

€650

€585

Per person

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4.6

SQUID FESTIVAL - Capraia and Elba on 14 meters wide

Italy: Tuscany

3 days - 2 nights

One departure available

October - November

€350

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

13642 reviews

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Relaxing weekend between Portovenere and the 5 Terre

09/18/2025

Silvia I.

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Italy

First experience on a sailing boat and it was very nice. Pleasant company and comfortable boat. Too bad for the weather that did not allow us to visit the Cinque Terre, we could certainly have been luckier! I recommend it.
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Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

09/17/2025

Mauro Z.

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Italy

Very nice cruise, despite the weather was not favorable, the skipper managed to let us enjoy the beauties of the Costa Smeralda
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Weekend at the Pontine aboard a splendid 16-meter sailboat

09/17/2025

Giulia E.

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Italy

It was my first time on a sailing boat but the skipper Leonardo and his wife Elena were immediately very professional and attentive to everyone's needs. The boat is very nice, functional and clean; perfect for enjoying the sea in total relaxation. The excellent company, the favorable weather and the crystal clear water of the Pontine islands then made the experience perfect!
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Egadi paradise for sailing and snorkeling

09/17/2025

Vicky H.

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Belgium

Mario is a competent and friendly skipper. The Egadi islands are beautiful and the boat is in good shape. It is a pity that 2 French-speaking fellow passengers had a lot of criticism, made little effort to involve the skipper in the conversations and were very present during the trip, to the displeasure of the other passengers.

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