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Yacht sailing holidays & skippered tours in Italy

Discover the beauty of Italy and treat yourself to a sailing holiday of relaxation, fun, and unique landscapes. Sail around the beautiful islands of Sicily and Sardinia, discover the Lipari, Pontine and Aegadian Islands by boat or anchor in the romantic bays of Tuscany or Cinque Terres.

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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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4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

2 departures available

September

Starting from

€312

Per person

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4.8

Super!

Elba, Tuscan archipelago or Corsica aboard a full opt catamaran.

Italy: Tuscany

7 days - 7 nights

One departure available

September

€850

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

5 departures available

September - October

Starting from

€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

2 departures available

September - October

€650

Per person

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4.8

Super!

Squid Festival: let's close the season on a high note! - on board a 17mt boat

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€280

Per person

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5.0

Super!

Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

Italy: Tuscany

2 days - 2 nights

One departure available

October

€250

€238

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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4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

One departure available

September - October

€680

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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4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

3 departures available

September - October

€325

€309

Per person

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4.7

Cous Cous Festival tra le Egadi e San Vito Lo Capo in Catamarano

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€850

Per person

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Reviews - Yacht sailing holidays & skippered tours in Italy

15011 reviews

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North Sardinia and South Corsica by catamaran with flybridge

09/13/2026

Carmen G.

-

GB

We had the most amazing week sailing around the north of Sardinia in a very comfortable boat. Chiara was a wonderful skipper but also a great host. It was an unforgettable experience.

South Sardinia - A Marine Paradise to Explore!

09/13/2026

Lorenzo M.

-

IT

A UNIQUE week!! Clean and very nice boat. Friendly skipper as well as very prepared. Special destination. I will be back soon with skipper Francesco.

Aeolian Islands: between sea and authentic flavours

09/13/2026

Francesco P.

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IT

Wonderful holiday in a fantastic setting. Crystal clear sea and breathtaking landscapes provided by the Aeolian Islands. Carlo has always been very helpful and very patient, as well as being very competent and also very nice. Highly recommended!
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La Maddalena Archipelago and southern Corsica

09/13/2026

Mauro F.

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CH

I am very pleased to leave this reference for a very simple reason: such a pleasant experience deserves to be shared. As I have already said to the Captain and Irene, a week with them "is not simply a holiday: it is an experience". We are talking about a Captain with over 40 years of experience, who has transformed his knowledge of the sea and navigation into a real profession. There are three aspects, in particular, that struck me: the crew, the experience and the travel philosophy. - The crew: Saverio and Irene are a very well-matched professional couple. Saverio is a person who has traveled the world and who, through cruising, has met many people, of all kinds. My impression was extremely positive: he is an authentic and genuine person. He says what he thinks, sometimes even in a rather direct and gruff way, but personally it is a quality that I appreciated very much. In a world where authenticity is not always taken for granted, finding it on board was a real breath of fresh air. Irene, on the other hand, is much more than what the word "sailor" might suggest. She is an extremely attentive girl, present and dedicated to her work. In just over two seasons, she has become a fundamental element of the team. Seeing her work on board was truly a pleasure: precise, tireless and always ready to take care of what is needed. Together, Saverio and Irene form a very complementary team, in which their different qualities are perfectly integrated. - Experience Here I think there is one of the most important aspects. Saverio has a life of navigation behind him, between crossings and travels around the world, and one thing is evident from the first moment: for him, safety comes first. Procedures, maneuvers, priorities and attention to sea conditions are not details, but an integral part of the way he steers the boat. When it's time to focus on sailing, he does it with great seriousness. Staying in the cockpit and watching him sail is, to all intents and purposes, a small school of sailing in the open air. It was very informative and, personally, it made me want to learn and understand this world even more. Irene, for her part, proves every day that she has earned her place on board. His attention and commitment are evident and I have great esteem for the work he carries out. - The philosophy of travel I think this is the main reason why I would come back on board. Their way of traveling "is not that of a traditional holiday", and this is probably its added value. There is no rigid itinerary decided months before. You decide day by day, evaluating wind, weather and sea conditions, choosing the coves and the best destinations at that time. To some it might seem like a lack of planning. In reality, after experiencing it, I think it's exactly the opposite: it's a smart way to make the journey safer and, at the same time, more beautiful. No one necessarily wants to reach "the most beautiful cove in Sardinia" if four hours later they risk finding themselves in the middle of a lump. Saverio's ability lies precisely in continuously finding the right compromise between safety, sea conditions and quality of experience. Our group (great group!) was lucky: Saverio and Irene made us discover beautiful places, allowing us to experience them with tranquility and in total safety. I could talk about many other aspects: about Irene's energy when she tells an anecdote, or about all those little attentions that made us feel really comfortable during the week and that, I imagine, are not necessarily "included in the program". And then there is a not insignificant detail: Saverio is also an incredible cook. Our group was followed with great attention throughout the week, also and above all at the table. Personally, I don't think it's easy to find crews so close-knit, helpful, competent and, above all, authentic. I would really like to meet Saverio and Irene again in the future. This was my first experience with them. And it certainly won't be the last. Greetings to both of you, Mauro Fadda

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Guides & tips


Italy

Tuscany, Sardinia, the Aeolian Islands and Liguria are just some of the most beautiful destinations for a sailing or catamaran holiday, let's discover them all!
Guide to Italy on a sailing boat

Tuscany

The island of Elba, Capraia, Il Giglio and Giannutri are just some of the best destinations for a sailing or catamaran vacation in Tuscany.
Guide to the Tuscany on a sailing boat

Aeolian Islands

Stromboli, Vulcano and Lipari are just some of the best destinations for a sailing or catamaran vacation in Sardinia.
Guide to the Aeolian Islands on a sailing boat

Sardinia

Costa Smeralda, Maddalena Archipelago and San Pietro Island are just some of the best destinations for a sailing or catamaran holiday in Sardinia.
Guide to the Sardinia on a sailing boat

Capri, Ischia and Procida

Enchanted landscapes and elegant haunts, thermal springs and seabeds full of surprises, simplicity and glamour: there is more than one reason to choose these timeless islands as a destination for a yachting holiday in stages.
Guide to Capri, Ischia and Procida on a sailing boat

Amalfi Coast

Positano, Amalfi and Cetara are just some of the best destinations for a sailing or catamaran holiday in the Gulf of Naples.
Guide to the Amalfi Coast on a sailing boat

WWF Whale watching cruises

A close-to-nature sailing cruise that integrates unrepeatable emotions and new scientific knowledge, perfect for true lovers of the sea, ready to have fun, wonder and delve into the magical world of cetaceans.
Guide to the WWF Cruises

Catamaran vacations

An alternative to the sailboat, the catamaran is an ideal choice for those who do not want to give up comfort and convenience and for a first vacation at sea.
Guide to the catamaran vacations

Flotilla holiday

A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays

Singles and solo travellers

Set out alone and return enriched by an unparalleled baggage of freedom, new friendships and lasting bonds. It is on a sailboat that an adventure as a solo traveler turns into a unique sharing experience.
Guide to solo travellers sailing holidays

Sailing vacations for families

To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
What to know before you go sailing with your family?

Sailing with children

Have you ever wondered if there is a vacation that is both the best for children and parents? The answer is yes, and it is indeed on a sailboat!
Guide to sailing vacations with children

Italy: the most beautiful places to sail

Italy: departures by month

Other travel ideas

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