As the cradle of the Renaissance, Tuscany and Umbria are famously graced with some of the world’s most mesmerizing art and architecture. They are also lands of lush, fertile landscapes, snowcapped Apennine mountains, and olive groves and vineyards that produce rich oils and world-famous wines.

The everyday beauty and unsophisticated, easy charm that welcomes you in these regions leave no doubt that these are places apart. The narrow medieval lanes and stony piazzas of Lucca; the morning mists in the valley below Assisi; the sublime art and architecture of Gothic Siena—these are near the top of the list of the pleasures that lie in wait for you in this stretch of Italy, but so are so many other sights and experiences. Just for starters, consider also:

Piazzas -- Piazza del Campo, the scallop-shaped setting for Siena’s famous Palio race, is the heart of the city and an icon of medieval town planning. Simple and serene, Todi’s Piazza del Popolo is Umbria’s most majestic square, with 13th-century palazzi complemented by a 12th-century Duomo.

Churches -- Western art was born at the glorious Basilica di San Francesco in Assisi, the Gothic Upper Church of which houses Giotto’s 28-part fresco, “The Life of St. Francis.” Garish or glorious, there’s nothing on the planet quite like Orvieto’s Duomo, and don’t miss some gruesome interpretations of the Last Judgment inside.


Paintings -- Siena’s Museo Civico is a showcase for Ambrogio Lorenzetti’s civic “Allegories.” Umbria’s top gallery, the Galleria Nazionale in Perugia houses Perugino’s moving “Adoration” and Piero della Francesca’s “Annunciation,” painted in precise perspective.

Architecture -- No building in the world is more instantly recognizable than Pisa’s 12th-century Leaning Tower. Spoleto’s awe-inspiring Ponte delle Torri, 90m (295 ft.) above the Tessino gorge, is impressive enough—even more intriguing is how the Romans managed to build the aqueduct that preceded it.