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Sailboat yacht sailing holidays & tours in Italy

Discover more than 376 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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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

7 departures available

May - July

Starting from

€370

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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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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5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

€1,020

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

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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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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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

12675 reviews

April 25th: cetacean watching expedition in the Pelagos Sanctuary with WWF guide

04/28/2026

Michele B.

-

Italy

Relatively short but interesting sea outing, with an excellent skipper and WWF experts. On board a nice and multinational company. There has been no shortage of dolphin sightings.
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April 25th long weekend on the Island of Elba

04/27/2026

Andrea T.

-

Italy

3 days on the island of Elba... dream landscapes along the itinerary proposed by Marco and Carmen, a very clean and comfortable boat, which they take care of as if it were their home. Lots of laughter and good music (Sal Davinci ... we joke !!). For me Elisabetta after 23 years that I did not go sailing thanks to Marco I had the pleasure of helping him in navigation and it was a return to the past .... Marco is an excellent professional skipper available in every request ...... my partner Andrea did the baptism on board and it couldn't have gone better .... Carmen as a captain helper always available ready and kind .. We highly recommend trying to sail with them as it's not just seeing Unique places but living a fairy tale thanks Marco and Carmen from Andrea and Elisabetta
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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

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