Sail Italy

The Italian Collection: Up with the Very Best Places to Go Sailing 

Italy is a truly spectacular yacht charter destination, with a wide selection of diverse sailing regions. From the Tuscan Archipelago through the Pontine Islands out of Rome, the Gulf of Naples, Amalfi and Cilento Coasts, the Aeolian Islands south to Sicily, and last but not least the sailing mecca of Sardinia: all places famous for their spectacular scenery, fascinating history, traditional cultures and of course delicious cuisines.

A sailboat vacation is undoubtedly the very best way to explore Italy's coastal towns and islands, moving freely and independently from one unforgettable place to another and experiencing something different every day. Italy's popularity as a place to go sailing means there are plenty of quality boats available of all size and type for you to charter bareboat or in fully-crewed luxury. 

A Sailing Holiday in Italy: the Choice is Yours

Italy has so much to offer that forward planning your yachting holiday is essential. The regional sailing areas are diverse, the travel options getting to and from are varied, and the itinerary options are almost countless. One thing all sailing holidays in Italy have in common is that they truly reveal a country to heighten the senses. 

A big part of planning your Italian charter is selecting the type and size of boat for your holiday. Roomy catamarans are much in vogue, while for the traditionalist yachtsmen and women there's a good selection of modern monohulls as well.

Bareboat sailing in one of Italy's fabulous regional destinations is a straightforward undertaking for the suitably-able charterer. Or consider taking aboard a skipper, who will be responsible for your yacht as well as providing your meals. And a cook, for the ultimate luxury sailing holiday. Even experienced sailors, aware of all there is to pack into a group sailing holiday in Italy, often opt to hire a crew, one carefully chosen by us in consultation with our operators.

On a skippered or crewed charter, your crew not only takes care of the work, they are your travel guides too. A big part of any trip to Italy is living like the locals for a bit: eating, shopping and enjoying the entertainment as they do. With the support and local knowledge of your Italian-speaking crew, you're assured to get the best out of your holiday, with experiences you may otherwise miss.

We have special first-hand knowledge of this amazing charter boat destination, and would love to talk to you about your Italian sailing holiday plans. 

Our client reviews about charter sailing in Italy

We had a great time in the Aeolian Islands, and I highly recommend them as a destination. The beauty is that the islands each have a different character and are close to each other. The longest ‘passage’ is about 10 miles, and some are a lot shorter. Two of the largest islands, Vulcano and Lipari, are only 800m apart, but very different! The marinas are well located and were reasonably priced (€70-100 per night) and at Panarea there are only moorings but for €70 you also get a 24/7 water taxi service which was perfect. We found mid / late July to be superb.
David, New Zealand, Aug 16th, 2019
Rating: 5 / 5
We found the boat to be nicely designed and very comfortable. The sails were near new and a treat to sail with. The highlight destination was Capri where because of unsettled weather we stayed in the marina. We found a brilliant restaurant in Ana-Capri and enjoyed strolling the narrow streets. San Michelle villa was delightful. Service was 10/10. Mario at the marina went out of his way to help us with ideas advice and making sure we wanted for nothing. Peter, New Zealand, Oct 24th, 2018
Rating: 5 / 5
The cat performed well with everything working as expected. The only issue was batteries not lasting a night and having to run an engine both in the morning and again in the late afternoon when sailing and not motoring. Sails were easy enough to hoist and the electronics worked well. Lipari was a great spot to stop with a nice town to explore. But the nicest island I found was Panarea. Less tourists with very friendly locals. James, Australia, Jul 22nd, 2018
Rating: 4 / 5
The Aeolian islands are a beautiful part of the world with many highlights. The standout was watching Stromboli erupt at night from nearby offshore. Sail Connections service was as always excellent. Russell, Australia, Jul 16th, 2018
Just a quick note to say we had a fabulous holiday and fantastic charter. The boat was perfect and the skipper Salvo and hostess Lucia were excellent could not fault anything. Salvo took us to some amazing places, always had our comfort and safety in mind, and was a lovely guy, Lucia was an amazing cook we ended up having most of our meals on board she was so good, also great company and very friendly and helpful. Everyone at North Sardinia Sail were also helpful and very friendly. Tony, Australia, Aug 31st, 2016
I just wanted to say thank you. We had a great time sailing though Italy and we appreciate your help putting that together. We had a blast on the trip! Cilento is beautiful and I'm really glad we went south before heading across the bay to Capri and Amalfi. Happy to share more stories/insights from the trip so you can help other explore this beautiful region, Thanks again. John & Leah, USA, Sep 30th, 2015
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