Italy

Italy is really three charter destinations wearing one flag. Sardinia's north — the Costa Smeralda and the La Maddalena archipelago — has water so clear it reads Caribbean: granite islets, empty white beaches, and Corsica's Lavezzi islands a short hop across the strait. The Gulf of Naples serves la dolce vita: Capri's Faraglioni, pastel Procida, thermal Ischia and the Amalfi coast's cliff villages, best admired from the water where the tour buses can't go. And off Sicily's north coast, the Aeolians are a chain of seven volcanic islands where you can watch Stromboli sparking against the night sky from your cockpit.

Each area has its own character and crew. Sardinia is the sailor's pick — steady wind, wild anchorages, national-park mooring fields. Naples and Amalfi suit shorter hops, harbour nights and serious restaurants; it's also motor-yacht country. The Aeolians reward the curious: black-sand anchorages, hot springs, and legs of 10–25 miles between islands.

Italian charter weeks are as much about the table as the tiller. Marina towns double as culinary stops — Sardinian vermentino and porceddu, Neapolitan pizza in its birthplace, Aeolian capers and malvasia. Provision lightly and eat ashore often; that's the local way.