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Yacht sailing holidays & skippered tours in Italy

Discover more than 138 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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5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

August - October

Starting from

€689

Per person

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4.9

Super!

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

5 departures available

August - October

Starting from

€950

Per person

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4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

August - October

Starting from

€650

€585

Per person

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4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

August - October

Starting from

€590

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

August - October

Starting from

€600

€540

Per person

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4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

August - September

Starting from

€640

€576

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

5 departures available

August - October

Starting from

€1,550

€1,473

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August - September

Starting from

€1,020

€918

Per person

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4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

2 departures available

August - September

Starting from

€680

Per person

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5.0

Super!

Luxury routes among the wonders of Northern Sardinia with hostess

Italy: Northern Sardinia

6 days - 6 nights

2 departures available

August - September

€1,600

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August - September

Starting from

€550

€523

Per person

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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

One departure available

August - September

Starting from

€795

€716

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

13758 reviews

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Easter on the Island of Elba

04/9/2026

Miriam C.

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Italy

Very pleasant sailing experience. The boat was in good condition. Everything went according to expectations and the navigation was safe and relaxing. The only negative note concerns the owner, Enrico. During communications he was often grumpy, with a rather rigid attitude and not inclined to confrontation. This made the interaction less pleasant, especially at times when more availability and friendliness would have been useful. Overall, I recommend the experience for the quality of the boat and the service at sea, but I suggest the owner to improve the approach with customers to make everything really impeccable.
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Easter in Capraia and Corsica

04/9/2026

Monica L.

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Italy

Weekend absolutely up to expectations. Marco is a trained skipper, with great experience, very helpful, kind and caring towards his crew. His boat is hospitable and excellently cared for by him. All positive!!
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Easter: Whale Watching Expedition in Pelagos Sanctuary with WWF Guide

04/8/2026

Agnese F.

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Italy

Unique experience, with excellent chances of whale sighting. In 3 days we made 3 close sightings of dolphins and bottlenose dolphins
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Easter in Capraia and Corsica

04/8/2026

Giovanni G.

-

Italy

Unique and beautiful experience, from start to finish. Starting with the skipper: exceptional, inclusive and very experienced of the sea and the places visited, always constructive and aimed at making us live a positive experience; the places visited were beautiful, with exceptional views, small villages in the middle of nature, with trekking, walks and stops for local shopping; The company of the whole crew (and friendly boats) was fun and collaborative, aimed at creating an enjoyable group experience; The perfect boat, equipped with every comfort, including USB recharges for almost every bed just to give an example. An experience certainly to be repeated and that I recommend

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