San Gimignano, known as the "city of beautiful towers," had 72 towers in its heyday. Now 14 remain, and, rising above Tuscany's Elsa Valley, they make the town look like a mediaeval dreamscape. Take in the fresco-covered Collegiate Church, the Civic Museum and the views from atop 177-foot Torre Grossa. Daytrippers from Florence tend to fill up the streets during the day, so for a more up-close-and-personal look at the town, spend the night.

Nearly crossing northern Italy from the Adriatic Sea westward, Emilia-Romagna gets its name from Via Emilia, the Rimini-to-Piacenza ancient Roman road it straddles. With a rich mix of age-old agriculture and modern industry, the region is home to many historic and cultural gems, both in its larger towns like Bologna, Modena and Ravenna, as well as in its many small hilltop villages. Of course, the region’s best offerings also include native culinary wonders like parmigiano cheese and tortellini.

Ravenna once was the capital of the Byzantine Empire in Italy, and it still has amazing mosaics recalling that heritage. Also make sure you visit Dante's tomb, as well as the little pile of rubble where local residents hid his urn during WWII to prevent it from being damaged.

The biggest beach resort on the Adriatic Sea, Rimini is a favored Italian seaside holiday destination for Italians themselves. The city offers an impressive nine miles of beaches, though many of these have private access for the scores of hotels facing the shore. The old town, about a 15-minute walk inland, has many interesting sights, including the Arch of Augustus from 27 BC, and Tiberius Bridge from the early 1st century. Rimini also boasts many great restaurants and an energetic nightlife.

Centrally located Umbria's principal cities include Spoleto, Assisi, and Terni. The capital, Perugia, is famed for its chocolate. Take a tour bus or prepare for daredevil Italian drivers if you opt to rent a car. Assisi's Basilica has a host of treasures, including works by Giotto. The town is also home to the crypt of St. Clare, patron saint of television. St. Francis' meditation retreat is in the mountains to the north. Classes at Velia's Cooking Style in Terni make good use of local produce.