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Sailboat yacht sailing holidays & tours in Italy

Discover more than 72 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

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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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

3 departures available

October

€230

Per person

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5.0

Super!

Barcolana 58: a day at the most famous regatta in the world

Italy: Venice and the Gulf of Trieste

1 day - 1 night

One departure available

October

€280

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€750

€675

Per person

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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

Starting from

€453

Per person

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4.8

Super!

Squid Festival on the Island of Capraia - 2 boats in company (22 seats)!

Italy: Tuscany

3 days - 2 nights

One departure available

October

€280

Per person

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4.8

Super!

Squid Festival on the Island of Capraia - 2 boats in company (22 seats)!

Italy: Tuscany

3 days - 2 nights

One departure available

October

€280

Per person

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4.9

Super!

Adventure weekend in the Egadi Islands

Italy: Aegadian islands

3 days - 2 nights

5 departures available

October - November

€350

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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4.8

Super!

Experience the sea in October!

Italy: Tuscany

2 days - 2 nights

4 departures available

October

€200

Per person

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4.9

Super!

Two days in Elba without worries with a professional skipper

Italy: Tuscany

2 days - 2 nights

One departure available

October

€315

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

3 departures available

September - October

€370

Per person

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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailboat yacht sailing holidays & tours in Italy

13893 reviews

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Long Weekend Santa Candida - Ventotene

09/25/2026

Claudio Giuseppe L.

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IT

Super experience! Marco and Giada are fantastic! They know every corner of the Pontine Islands!

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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