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Sailboat yacht sailing holidays & tours in Italy

Discover more than 364 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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4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

13 departures available

June - September

Starting from

€680

€590

Per person

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4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

19 departures available

June - October

Starting from

€590

Per person

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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€1,260

€1,134

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

6 departures available

July - September

Starting from

€795

€716

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

11 departures available

June - September

Starting from

€600

€570

Per person

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4.7

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

Italy: Tuscany

6 days - 6 nights

One departure available

July

Starting from

€1,052

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

5 departures available

June - September

Starting from

€950

€855

Per person

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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

12 departures available

June - October

Starting from

€689

Per person

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4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

One departure available

August

€890

Per person

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4.6

Long weekend between Ponza and Palmarola: adventure at the Pontine!

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€490

Per person

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4.7

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

39 departures available

January - December

Starting from

€300

€270

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

5 departures available

June - September

Starting from

€999

€949

Per person

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Reviews - Sailboat yacht sailing holidays & tours in Italy

12746 reviews

Long weekend of June 2nd on the Costa Smeralda

06/4/2026

Silvia B.

-

IT

Francesco guided us in the world of relaxation and zero stress, lulled by the sea, following the rhythm of the sun and the delicious dinners prepared by him, transmitting his love for sailing and for [hidden]. Removed the watch and forgotten the cell phone, the only commitments are swimming, balancing on. Sup, prepare loaded spritzes and exchange jokes and life anecdotes with those who become your roommates (in this case excellent) for a few days. Thank you Francesco and thank you crew!

June 2nd long weekend: discovering Capri, Ischia and Procida

06/4/2026

Ivana G.

-

IT

Very comfortable, spacious and clean sailboat. Gennaro proved to be a nice and helpful skipper, helping to make the experience on board pleasant, and also participating in land trips. Less convincing, however, was the management of the itinerary: the moorings were often far from the coast, even with favorable weather conditions, and the stops did not allow you to explore exclusive places that could only be reached by sea. Furthermore, despite being part of the program, the tender was never used, limiting the possibilities of visiting coves and more hidden areas. Overall, a relaxing and pleasant experience, but below expectations in terms of exploration and itinerary, considering that the context would have allowed it.

June 2 long weekend between Capraia and Corsica - 2 boats

06/4/2026

Rebecca C.

-

IT

It was a beautiful holiday, we sailed between Elba and Capraia and both Matteo and Alessio (the skippers of the two boats) were impeccable, really good and professional. On board I found a wonderful company that made these 4 days truly unforgettable! Super recommended experience
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Four days in the Pontine Islands

06/4/2026

Guido V.

-

IT

Super experience with Dario!! I highly recommend it. Thank you Dario and see you next time

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