▲▲▲ Venice Dreamy island city, powerful in medieval times; famous for St. Mark’s Basilica, the Grand Canal, and singing gondoliers.
▲▲▲ Cinque Terre Five idyllic Riviera hamlets along a rugged coastline (and part of a national park), connected by scenic hiking trails and dotted with beaches.
▲▲▲ Florence The cradle of the Renaissance, with the world-class Uffizi Gallery, Brunelleschi’s dome-topped Duomo, Michelangelo’s David, and Italy’s best gelato.
▲▲▲ Siena Florence’s smaller and (some say) more appealing rival, with its magnificent Il Campo square, striking striped cathedral, and medieval pageantry.
▲▲▲ Rome Italy’s capital, the sprawling Eternal City, studded with Roman ruins (Forum, Colosseum, Pantheon), romantic floodlit-fountain squares, and home to Vatican City and the astonishing Sistine Chapel.
▲▲ Milan Powerhouse city of commerce and fashion, with the prestigious La Scala opera house, Leonardo’s The Last Supper, and three airports.
▲▲ Heart of Tuscany Picturesque, wine-soaked villages of Italy’s heartland, including mellow Montepulciano, Renaissance Pienza, and Brunello-fueled Montalcino.
▲▲ Assisi St. Francis’ hometown, perched on a hilltop, with a divinely Giotto-decorated basilica.
▲▲ Orvieto and Civita More hill-town adventures, featuring Orvieto’s classic views, Classico wine, and ornate cathedral plus pint-sized, hilltop village of Civita di Bagnoregio.
▲▲ Naples Gritty, in-love-with-life port city featuring vibrant street life and a top archaeological museum starring the treasures from ancient Pompeii.
▲▲ Amalfi Coast and Paestum String of seafront villages — including hilly Positano and workaday Amalfi — tied together by a scenic mountainous coastal road. Farther south is Paestum, with its well-preserved ancient Greek temples.
▲▲ Pompeii and Nearby Famous ruins of the ancient towns of Pompeii and Herculaneum, with their nemesis, Mount Vesuvius, looming on the horizon.
▲ The Lakes Two relaxing lakes, each with low-key resort towns and a mountainous backdrop: Lake Como, with quaint Varenna and upscale Bellagio; and Lake Maggiore, with straightforward Stresa, manicured islands, and elegant villas.
▲ Near Venice Several interesting towns: Padua (with Giotto’s gloriously frescoed Scrovegni Chapel), Vicenza (Palladian architecture), and Verona (Roman amphitheater plus Romeo and Juliet sights).
▲ The Dolomites Italy’s might alps, featuring Bolzano (home of Ötzi the Iceman), the charming village of Castelrotto, and Alpe di Siusi (alpine meadows laced with lifts and hiking trails).
▲ Riviera Towns More Italian Riviera fun, including the coastal towns of Levanto, double-beached Sestri Levante, the larger Santa Margherita Ligure, gem-like Portofino, and to the south, resorty Porto Venere.
▲ Pisa and Lucca Two classic towns: Pisa, with its iconic Leaning Tower and surrounding Field of Miracles, and Lucca, with an inviting old center, encircled by a wide medieval wall you can stroll or bike.
▲ Volterra and San Gimignano Two hill towns in northern Tuscany: vibrant, refreshing Volterra and multi-towered, touristy San Gimignano.
▲ Sorrento and Capri The seaside resort port of Sorrento, and just a short cruise away, the jet-set island getaway of Capri, with its eerie Blue Grotto.