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Yacht sailing holidays & skippered tours in Italy

Discover more than 188 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

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

4 departures available

August

Starting from

€900

Per person

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4.5

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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4.6

Premium

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

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August - September

Starting from

€1,640

€1,558

Per person - min 2 pax

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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

4 departures available

August - September

Starting from

€600

€570

Per person

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4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

One departure available

August - September

Starting from

€950

Per person

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4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

August - September

Starting from

€590

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

2 departures available

August - September

Starting from

€795

Per person

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4.8

Super!

Sailing and Freediving in the sea of Sardinia and Corsica

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€870

Per person

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4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

4 departures available

August - September

Starting from

€900

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

3 departures available

August - September

Starting from

€690

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

3 departures available

August - September

Starting from

€1,041

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€1,100

Per person

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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

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Reviews - Yacht sailing holidays & skippered tours in Italy

14140 reviews

Escape to Elba: wind, sea and freedom in a weekend

07/12/2026

Sara M.

-

IT

Everything nothing short of fantastic !! Experience to be repeated !! skipper Marco nice helpful and very very capable 😊

Weekend Elba or Capraia

07/12/2026

Federico M.

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IT

I had fun and learned some rudiments of sailing thanks to Andrea who allowed those who wished to help him in maneuvers and navigation. Too bad we couldn't set sail on Friday evening but unfortunately the sea conditions did not allow us. Rosignano is a convenient port for those coming from the north but a bit far from Elba and Capraia for only two days.
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All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

07/12/2026

Axel G.

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DE

We enjoyed the sailing trip very much, the skipper was extremely nice, helpful and courteous. We were able to see a lot, and capture the typical of the islands and the Amalfi Coast. We also had a very nice family of sailors on board. Only the wet room could have worked and smelled a little better. What we didn't really realize, however, was that everything inclusive did not refer to the food on board, but obviously only to the sightseeing destinations. This is misleading and should be better formulated in future offers!

Midweek relaxing in the Pontine Islands

07/12/2026

ELSA CHRISTINE JOSETTE B.

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IT

Beautiful sailing experience. The Pontine islands are wonderful and we enjoyed the cruise together with the rest of the crew and our skipper Mirko, very helpful and attentive to everyone's well-being. We will leave on a sailing boat with great pleasure and I thank Mirko again for making our holiday special.

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