Sail Italy

Italy is a truly spectacular yacht charter destination. 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 these places are 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.

Around Italy, arranging a bareboat charter is quite straightforward for the suitably-able sailor. Alternatively, consider taking aboard a skipper, who will be responsible for your yacht as well as providing your meals. You can even take a cook along if you seek the ultimate holiday. Even experienced sailors often prefer to hire a crew, carefully chosen by us in consultation with our operators. These people not only take care of all the work, they are your local guides too. It's fun to live like the locals for a bit, eating, shopping and being entertained as they do. With the help and local knowledge of your crew, enjoy the very best in holiday experiences that may otherwise be missed.

With native Italian-speaking staff aboard, we have special knowledge of this amazing charter boat destination. We'd love to talk to you about your Italian sailing holiday plans. 

Receive a personalized proposal with boat, cost and extra options as applicable.

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One contact - every option - advice you can trust.


  • Matching any competitive offer
  • Sourcing boats with discounts available
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  • Qualifying the operator as well as the boat
  • Advising without bias based on 25+ years of experience
  • We do more than just book yachts!

We will match any discount website offer on charter boat price, and still provide our customary high level of service.

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The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is jam-packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

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