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Yacht sailing holidays & skippered tours in Italy

Discover more than 39 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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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

One departure available

September - October

€700

Per person

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4.7

Premium

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September - October

Starting from

€1,640

€1,558

Per person - min 2 pax

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€750

€675

Per person

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5.0

Super!

Weekend on Elba on a 16-meter sports boat

Italy: Tuscany

2 days - 2 nights

One departure available

September

€400

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

September - October

€370

Per person

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4.8

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

One departure available

September

€300

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

One departure available

September

Starting from

€230

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

September

€370

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

One departure available

September - October

€650

Per person

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5.0

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

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September - October

€690

Per person

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New

Cruise between the Maddalena archipelago and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September - October

Starting from

€585

Per person

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4.9

Aeolian Islands in a big and new catamaran: sea, sun, relaxation

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September - October

€980

Per person

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Reviews - Yacht sailing holidays & skippered tours in Italy

15093 reviews

Feast of Santa Candida in Ventotene

09/24/2026

Alessandra B.

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IT

Nice experience, choreographic and spectacular party, young but very professional skipper, the only negative judgment concerns the boat. I thought the maintenance was poor: exhausted gas cylinder (there was a spare part and it was replaced, but strange not to think about it before boarding), broken light in the cockpit, defective anchor winch, defective stove, defective tender motor, very old and ruined sails.
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Midweek weekend in Elba: sea, scents, colors

09/24/2026

Cecilia M.

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IT

Good morning, I am happy that the sea and wind conditions have allowed us to really go sailing, I have learned that waves and wind are not always in agreement, I have understood how the compass works with degrees, thanks also to the great experience of Ivo who explained everything to us. Elba is so rich that it deserves many more days and means to get closer to the rocks and swim in the caves. On the whole, I would say that I perceived the somewhat austere beauty of sailing in the Tuscan islands. thanks, Cecilia

Feast of Santa Candida in Ventotene

09/24/2026

erminio b.

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IT

the holiday went smoothly, the skipper (Francesco) professional, helpful, and prepared. the right and assorted company. The boat would need small precautions to make the experience even more enjoyable. ( bins in the bathrooms, a diffused light for the night in the dinette, a diffused light in the cockpit, updated instrumentation. On the other hand, the USB sockets in the cabin and the provision of sheets and towels included in the price are very appreciated.
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Relaxing weekend and sailing school

09/24/2026

Giacomo G.

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IT

I can't give more than 5 stars. The Sailsquare platform responded quickly to my requests by hitting the target. Contact with Edoardo was very precise, right information at the right time. At the beginning of the course, the short theoretical briefing loaded us with notions in a couple of hours... This made us understand further techniques of life on a boat. For us it was the first time. Navigation? Wow !! Let's fly Super Edoardo!! Super recommended cruise/course! The boat has all the spaces to live comfortably, probably the weather conditions have also helped us a lot. Undoubtedly also the other guys who participated, like us, contributed a lot to make the weekend wonderful 🤩

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