The dramatic Dolomites mountain range, with its jagged peaks and green valleys, leads you to the picturesque town of Bassano del Grappa. As you cross the River Brenta via the city’s red-tiled covered bridge — designed in 1569 by architect Andrea Palladio — you’ll enter Veneto-style arcaded streets that open to piazzas encircled by churches, shops and cafés. Tasty Tip: Sit down to a feast of local specialties like white asparagus pesto paired with grappa, a strong liqueur first produced in the area.

Tuscany’s medieval towns captivate with panoramic views of rolling hills, streets reminiscent of a Renaissance painting and ancient churches and squares. Here, perched atop one of the region’s spectacular hills, you’ll discover the area’s winemaking history as you sip samples of Chianti at Verrazzano Castle, where ancient cellars date back to the 16th century. In nearby San Gimignano, view the remaining 13 of 72 towers built in the 14th century as you learn the history of these ancient Etruscan ruins.

Discover the magic of Cinque Terre, a string of five medieval seaside villages nestled on the Italian Riviera and home to some of the country’s most glorious natural scenery. Pastel-colored homes dot terraces built into steep mountains that plunge starkly into the azure sea. Soak up the sun as you swim, feast on fresh seafood and trek by foot to enjoy some of the most picturesque views in all of Italy.

Capri has long been one of Europe’s most beloved escapes, appealing to Roman emperors and the glitterati alike. You’ll feel like a celebrity when you journey to the island by boat or helicopter, taking in the limestone sea stacks dominating the landscape. Travel by boat through the three-foot-high cave mouth into the spectacular Blue Grotto, a stunning display of sapphire-hued water surrounded by stone walls. Travel Tip: We recommend taking a chair lift up Monte Solaro for sweeping views of the Faraglioni rock formations that jut out of the sea. Or, for another easy form of transportation, take the funicular from the Marina Grande to the center of Capri, climbing uphill past fragrant lemon groves.