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Yacht sailing holidays & skippered tours in Italy

Discover more than 48 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

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

One departure available

September - October

€700

Per person

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4.7

Premium

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

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September - October

Starting from

€1,640

€1,558

Per person - min 2 pax

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5.0

Super!

Weekend catamaran in Portovenere and Cinque Terre

Italy: Liguria

3 days - 2 nights

One departure available

September

€212

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

One departure available

September

Starting from

€230

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€750

€675

Per person

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4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

One departure available

September

€790

Per person

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4.8

Super!

COUS COUS FEST: Un Week End di Mare, Vela, Cous Cous e Musica!

Italy: Sicily

4 days - 3 nights

One departure available

September

€345

Per person

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5.0

Super!

Weekend on Elba on a 16-meter sports boat

Italy: Tuscany

2 days - 2 nights

One departure available

September

€400

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

September - October

€370

Per person

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4.8

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

One departure available

September

€300

Per person

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4.8

Super!

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

Italy: Tuscany

2 days - 2 nights

One departure available

September

Starting from

€230

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

September

€370

Per person

Why book a holiday with Sailsquare?

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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

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

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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

15070 reviews

Comfortably Aeolian Islands: Catamaran Cruise with Steward

09/21/2026

Pierluigi O.

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IT

Spectacular catamaran. Well structured itinerary. A truly unforgettable experience in the Aeolian Islands! The catamaran was the perfect way to experience the sea, but what really made the difference was the professionalism and passion of the skipper and cook on board. Angelo, the skipper, proved to be a true sea dog: a great connoisseur of the islands, always attentive to the conditions of the sea and the needs of all of us. He took us to wonderful bays and coves, making us discover spectacular corners and making every navigation pleasant and safe. His experience and tranquility allowed us to enjoy every moment without worries. And then the cook, Diego, a real surprise! Every day he delighted us with delicious dishes, well-kept and rich in flavors, enhancing the specialties and products of the territory. Eating on board, with the Aeolian sea in front of our eyes, was one of the best moments of the holiday. A professional couple who, with competence, availability and sympathy, made the trip even more special. An experience that I absolutely recommend and that I would do again without hesitation!
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Mini-cruise with WWF guide in the heart of the Tuscan Archipelago

09/21/2026

Gioia S.

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FR

Amazing experience ! I recommend this alternative method of holidays to everyone to have a little more awareness of the world in which we live and to continue to discover the sea.... I will definitely do it again!
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Egadi Islands by catamaran

09/21/2026

Marco C.

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IT

From 12 to 19 September a memorable week. Giuseppe (the skipper) excellent travel companion, experienced and professional. As he says... TOP! He is a great connoisseur of the Egadi Islands and shrewd in every detail. He makes you feel at home in his catamaran that he loves and shares with passion. What can I say, certainly to be repeated.
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Learn to sail in Liguria: First level sailing course

09/21/2026

Valentina G.

-

IT

Orazio is an excellent skypper, helpful and attentive, he taught us a lot and we had fun! Highly recommended!

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