See Venice, then head to Veneto
Once you’ve explored the picturesque canals of Venice, head farther into the region of Veneto. Away from the coast you’ll find the towns of Verona and Padua, where Shakespeare set his plays Romeo and Juliet and The Taming of the Shrew. In Verona, stroll through the charming, romantic plazas and hear an outdoor concert at a First-century Roman amphitheater. In the University town of Padua, explore the Prato della Valle, one of Italy’s largest piazzas surrounded by water and statues.
See the Amalfi Coast, then head to Puglia
Puglia, an Adriatic Sea town in the heel of Italy’s boot, is quieter and less frequented by tourists than the Amalfi Coast. In addition to sunbathing on gorgeous beaches, see the historic architecture of Castel del Monte and the trulli of Alberobello, both recognized as UNESCO World Heritage Sites. Make sure to book a table at Grotta Palazzese to dine inside a carved-out limestone cave with a view of the sea.
See Florence, then head to Emilia-Romagna
Emilia-Romagna is one of Italy’s smallest regions, but for foodies it is not to be overlooked. The historic towns of Bologna and Parma (which gave their names to your favorite charcuterie) are culinary havens. Visit a Parmigiano-Reggiano or balsamic factory, take a home-made pasta-cooking class and feast on meats and cheeses at a countryside osteria. When you can eat no more, visit the authentic Ferrari museum in the region where Ferraris and Lamborghinis are made.
See Tuscany, then head to Umbria
After you’ve gotten your fill of the Tuscan countryside, head east to neighboring Umbria for a quiter, laid-back experience (thanks to fewer tourists). Called the “green heart” of Italy, it’s home to verdant hills and vineyards, medieval villages and authentic cuisine. Visit the town of Norcia, which is famous for truffles and wild-boar sausage, and sample wine in the hamlet Montefalco, which is known for the Sagrantino grape.
See Milan, then head to Piedmont
Escape the hustle and bustle of metropolitan Milan in nearby Piedmont. The region is famous for its medieval towns and sweeping landscapes, which are situated against the Alps. Visit the town of Canelli, where an “underground cathedral” of connected cellars makes sampling spumanti wine a breeze. Join experienced truffle hunters and dogs on the search for world-renowned white truffles, and then enjoy a lavish truffle-based lunch paired with red wine and local specialties.