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Yacht sailing holidays & skippered tours in Italy

Discover more than 92 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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4.7

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€420

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

September - October

Starting from

€950

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

3 departures available

September - October

Starting from

€1,640

€1,558

Per person - min 2 pax

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5.0

Super!

Weekend catamaran in Portovenere and Cinque Terre

Italy: Liguria

3 days - 2 nights

One departure available

September

€212

Per person

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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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5.0

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€550

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€441

€419

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

Starting from

€370

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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4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

2 departures available

September

Starting from

€230

Per person

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4.8

Super!

COUS COUS FEST: Un Week End di Mare, Vela, Cous Cous e Musica!

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

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

2 departures available

September - October

€690

Per person

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Reviews - Yacht sailing holidays & skippered tours in Italy

14989 reviews

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Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

09/9/2026

Giovanna G.

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IT

I must say that everything went very well! First experience in the flotilla and it was super! I recommend to all those who want to have a fun-filled holiday!

Gargano National Park and Marine Protected Area of the Tremiti Islands

09/9/2026

Valentina D.

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IT

Lovely places, Marco is an expert reference point that allows you to appreciate the beauties and peculiarities of the place that he knows very well. He also pampered us with his skills as a chef, delighting us on one occasion with fish caught even from our boat. Recommended.

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

09/9/2026

Massimiliano P.

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IT

The amount paid seemed a bit disproportionate considering the condition of the boat, the services offered and the number of people on board, 12, A bit too many in my opinion, also but not only in consideration of the price. You couldn't all sit in the cockpit and it was difficult to move. The skipper is competent but often appeared too nervous and in some cases paradoxically offensive even towards his customers. The tour overall was still interesting.
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Amazing Pontine Islands on a sailboat with private bathrooms

09/9/2026

Elena B.

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IT

A weekend dedicated to well-being and beauty. Comfortable boat (5 cabins with private bathrooms), clean, spacious and well maintained; skipper Dario and his right hand Enrica were helpful, kind and accommodating from the start. Perfect organization... it would take a thousand weekends like this! Thank you thank you

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