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Yacht sailing holidays & skippered tours in Italy

Discover more than 38 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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4.6

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

Italy: Northern Sardinia

6 days - 7 nights

One departure available

September - October

Starting from

€650

€585

Per person

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4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

One departure available

October

Starting from

€950

Per person

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4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

October

Starting from

€590

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

October - November

Starting from

€1,160

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

October - November

Starting from

€600

€540

Per person

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4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

One departure available

October

Starting from

€860

€774

Per person

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4.8

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

October

Starting from

€640

€576

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€320

€272

Per person

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4.9

Super!

Trip with photographer to the Pontine - Life changing experiences

Italy: Pontine Islands

4 days - 3 nights

One departure available

September - October

Starting from

€420

€399

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

4 departures available

October

Starting from

€230

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

4 departures available

October

Starting from

€230

Per person

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5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

4 departures available

October

Starting from

€800

€720

Per person

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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.

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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

13761 reviews

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Weekend among the most beautiful coves of Elba

04/21/2026

SARA N.

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Italy

Unforgettable sailing experience with Marco and Carmen! 🌊⛵ From the first moment we felt welcomed as friends: professional, helpful and always attentive to every detail. The weekend was well organized, with breathtaking views, moments of relaxation, aperitifs and lots of laughter. We sailed to the island of Elba, saw dolphins and caught some excellent fish that we then cooked and ate together. All wonderful! Marco is an experienced skipper who conveys safety and passion for the sea, while Carmen adds a special touch with her kindness, sympathy and care for guests. I recommend this experience to anyone who wants to experience the sea in an authentic and relaxing way. Definitely to be redone, we will see each other 😜 again

Easter in Capraia and Corsica

04/14/2026

Giunio M.

-

Italy

Wonderful days in the company of quiet people and lovers of the sea and sailing

Offshore and night navigation course on cabin cruisers

04/13/2026

Marco B.

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Italy

Sailing course... but also a holiday. Navigation to Giglio and back via Elba with departure at night. Despite the little wind that blew in those days, Paolo was able to convey notions and make the students practice, all with the utmost sympathy ... Be prepared to be made fun of, especially if you're an engineer.
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Easter on the Island of Elba

04/9/2026

Miriam C.

-

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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