8 Small Towns in Italy That Are Worth a Detour

Romans have been escaping the chaos of the city with a jaunt to the Castelli Romani since the time of Caesar Augustus. These verdant hills just south of Italy’s capital are known for their two volcanic lakes, papal summer residence in Castel Gandolfo, and a smattering of pretty hilltop towns. The most famous of these is Frascati, just a 30-minute train ride from Rome. There, wander the lively town center—stopping to admire its collection of elegant Renaissance and baroque Tusculum Villas—before stopping to sample the area’s flagship white wine.

Set along the main train line and highway between Rome and Florence, Orvieto makes for a convenient and picturesque stop to break up your trip. You can’t miss this clifftop city, looming from its perch atop a volcanic butte 1,000 feet (304 meters) above the surrounding plain. The headliner here is the duomo (cathedral), arguably one of the most dazzling in Italy—try to time your visit for late afternoon when the setting sun makes the facade mosaics glitter golden. Below ground, you can also tour the warren of tunnels, chambers, and wells beneath the town center.

UNESCO-listed Pienza is beautiful inside and out. The compact town center is a treasure trove of stately Renaissance architecture, including the Cathedral, Papal Palace, and Town Hall lining the main square. Turn your gaze outward and you’re rewarded with views over the Val d’Orcia, Tuscany’s most picturesque countryside. Then, browse the local shops—stocked with everything from high-end antiques to fragrant wheels of pecorino (sheep cheese)—before relaxing over lunch with a bold red from the wineries in neighboring Montepulciano.

Once a sleepy village, today San Gimignano is one of the most famous small towns in Tuscany. Visitors flock to see its UNESCO-listed walled old town and 16 historic towers (what remains of more than 70) during the peak summer months, so visit during spring for a more relaxed vibe. Just an hour from Florence, this “medieval Manhattan” is a popular day trip, often paired with a winery tasting or lunch and scenic horseback ride in the Chianti hills. For the best views over the surrounding Val d’Elsa, climb Torre Grossa (Great Tower) or take the 2-mile (3.5-kilometer) walk around the perimeter of the 13th-century city walls.

Most day trips from Florence head south into the Chianti countryside, but there are plenty of equally delightful small towns to explore north of the Renaissance capital. The village of Brisighella—largely overlooked by tourism—offers a particularly refreshing departure from the crowds. This medieval gem is known for its Via del Borgo (or Via degli Asini), a 14th-century covered walkway, and its atmospheric maze of cobblestone lanes lined by pastel-hued palazzi. Take the Via della Rocca trail through olive groves to reach the Rocca (medieval military fortress) and the Torre dell’Orologio (clock tower). From here, the view stretches for miles.

Ferrara is a striking Renaissance town, but one that most travelers to Italy have never heard of. Stronghold of the powerful Este dynasty from the 13th to the 16th centuries, this UNESCO-listed treasure is overshadowed by the star power of nearby Venice. You’ll feel like the only tourists in town while taking in its sights—including the moat-lined Este Castle, intact medieval city walls, and ornate cathedral—or exploring its historic center, bustling with locals on bicycles going about their day with loaves of star-shaped coppa ferrarese bread poking out of their baskets.

Unsung Padua is home to the Scrovegni Chapel (brilliantly frescoed by Giotto in the 14th century), one of Italy’s artistic masterpieces which was named a UNESCO World Heritage Site in 2021. Other highlights in this small art city, pilgrimage destination, and vibrant university town situated just 30 minutes from Venice include the Basilica of Saint Anthony of Padua and the 16th-century Botanical Garden, the first of its kind in the world.

Insider tip: To visit the Scrovegni Chapel, book in advance. Viewing time inside the chapel is about 15–20 minutes.

If you need a break from the throngs in Venice but even Padua is too big to satisfy your small-town craving, head to Bassano del Grappa. As its name suggests, this picturesque town in Veneto’s Alpine foothills is most famous for its fiery grappa—a distilled spirit made from grape must—and there are a number of landmark distilleries that offer tours and tastings in town. Teetotalers have plenty to do here, too, including strolling over the 16th-century Palladian covered bridge which spans the Brenta, meandering the streets of the medieval old town, and visiting World War I museums.