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Sailboat yacht sailing holidays & tours in Italy

Discover more than 375 opportunities to get on board a Sailboat adventure in Italy. 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

15 departures available

June - October

Starting from

€689

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

16 departures available

May - October

Starting from

€650

€585

Per person

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4.6

Weekend "nel Blu dipinto di Blu" - Ponza & Palmarola

Italy: Pontine Islands

3 days - 2 nights

6 departures available

May - June

Starting from

€230

Per person

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4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

21 departures available

May - October

Starting from

€590

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

14 departures available

June - September

Starting from

€680

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

8 departures available

April - July

Starting from

€360

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

22 departures available

May - November

Starting from

€600

€540

Per person

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4.8

Super!

From Cagliari to Cannigione.. exploring the east coast of Sardinia

Italy: Southern Sardinia

6 days - 7 nights

One departure available

May

€550

Per person

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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

Starting from

€1,020

€918

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

5 departures available

May - July

Starting from

€350

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

8 departures available

July - 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

12 departures available

June - September

Starting from

€550

€523

Per person

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Reviews - Sailboat yacht sailing holidays & tours in Italy

12673 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.

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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.

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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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