Within their stone ramparts, the proud hill towns of Tuscany and Umbria offer a blissful escape from the 21st century. With local expert Giovanni Adreani, explore Cortona from its Etruscan tombs to its historic neighborhoods. In Todi, linger in the Piazza del Popolo, one of the prettiest squares in Italy. And uncover Assisi with guide Rosella Fiorucci, who knows Saint Francis’ hometown "come la sua tasca" ("like her own pocket").

Something about Italian cuisine appeals to the soul. Straightforward and honest, it celebrates fresh ingredients prepared with minimal manipulation – proud but not boastful. A glass of red wine, thinly sliced prosciutto, warm bruschetta, some aged parmigiano reggiano splashed with balsamic vinegar – it’s habit-forming! Discover the joys of the Italian table in true Backroads style, with a cooking demonstration and hands-on lesson, an exclusive chocolate factory visit, superb picnics and unforgettable dinners.

Fall in love with Siena as you explore the city’s handsome medieval center with local guide Laura Antoni. Learn about its 17 fiercely competitive contrade (districts). Admire the black-and-white striped façade and exuberant ornamentation of the Duomo. Linger at the Piazza del Campo and imagine how it looks twice a year – filled with dirt, galloping horses and frenzied spectators – during the city’s famous Palio bareback race.

Even if you’re new to the pleasures of the vine, this trip is sure to unleash your inner oenophile. Enjoy a private tasting of Chianti Classico produced on the vineyard-covered estate of Borgo Scopeto, just outside of Siena. Down south on a lofty Umbrian hilltop is Orvieto, where you can try the fine white wines that have been praised by artists, poets and nobles since the Middle Ages. Though the dry version predominates, also be sure to taste the semisweet abboccato variety. Cin cin!

The origin of Italian ceramics dates back to the Etruscans, but it was not until the Renaissance that the art of majolica reached its full splendor, with brilliant colors and refined decorations. In Deruta, one of the world’s oldest ceramics centers, you can paint your own piece during our private class at a prestigious regional pottery producer.