The Mediterranean's biggest island is separated from the mainland by the Strait of Messina. A mountainous spot, Sicily's coast and its small islands sit at the foot of volcanoes, including Etna, Stromboli and Vulcano. The Greeks, Romans, Normans and Catalans all left their mark on the island in the form of Byzantine palaces, Gothic castles and Baroque flourishes in capital Palermo. Most larger towns offer interesting museums, but Etna and the Hellenic temples in Agrigento offer particularly unique sights.

Though Cefalu is considered one of Italy’s finest resort towns, there’s more to do than just swim and sunbathe. The seaside spot, poised on Sicily northeastern coast, is equally celebrated for its Norman cathedral, medieval old town, archaeology museum, and seafood-heavy fare.

If you come across "cipolla di Tropea"-flavoured gelato, you might worry that you’ve forgotten your Italian… or are losing your mind. Don’t fret. "Cipolla" does mean onion, and yes, that is indeed onion gelato. The local red onions are so popular that they’ve even made it into dessert. Tropea, like so many towns on the Amalfi Coast, has a gorgeous cliffside setting. Beneath those cliffs, you’ll find beautiful, sandy beaches.

Getting to hilltop Orvieto is half the fun, with the choice of ascending by escalator or funicular cable car. The strategically built old town is free from modern-day traffic, inviting visitors to enjoy a taste of medieval Umbria—and a glass of famous Orvieto Classico wine.

While many visitors come for the beaches, arts celebrations and fiestas, San Sebastian-Donostia is serious about its food and drink. The Old Quarter’s narrow, winding streets are full of bars and restaurants, and in the modern city, sidewalk cafes are all around. The city specialises in seafood. Just make sure you know not to expect dinner at 6 or 7 p.m.—that’s much too early in Spain. Instead, tide yourself over with tapas, and enjoy eating and drinking late into the night.