Situated Between Rome And Florence Is A Hilltop Italian Town With Medieval Alleys And Mouthwatering Local Wine

Less than two hours drive north of Rome, nestled in the culturally rich region of Umbria, the hilltop town of Todi is one of those spots that's popular with locals but often overlooked by international tourists. Home to a layer cake of history that goes much further back than the Ancient Romans, Todi's story starts in the 8th century BC, a borderland between the Ancient Umbrian and Etruscan settlements that became part of the Roman Empire in 89 BC. 

Today Todi is a peaceful gem of winding medieval alleys and grand piazzas full of impressive Gothic and Renaissance architecture, including grand palaces, churches, and a stunning cathedral. Driving is the easiest way to reach the old town, as its two nearest train stations are some way outside the city center and require a change from hubs like Florence.

Much like its neighbor Tuscany, Umbria produces some exceptional wines. Orvieto and Sagrantino wines come from this Italian region where you can experience similar Tuscany vibes but with less crowds. Umbria's also generally a cheaper option than its neighbor Tuscany, with prices for dining out or accommodations coming in at 15% to 25% less, making Todi a great destination if you want your dollars to go a little further. With cute guesthouses or apartments starting at $80 to $110 per night, it's a steal compared to Florence. Of course it's much smaller than the Tuscan capital, but there's still plenty to see and do in Todi.

Pack your walking shoes for this sojourn as once you've taken the free funicular up into hilltop Todi, there's more incline to come. All alleys lead to Piazza del Popolo (pictured), the town square that has been the heart of Todi for 2,000 years since the Ancient Romans built their forum marketplace here. It's one of the region's best preserved medieval squares, lined with gothic and renaissance buildings. The 12th century Cattedrale di Santa Maria Annunziata is a very stirring space, with tinted light pouring in from the round rose window and beautiful frescoes — The Last Judgement taking its inspiration from the more famous version in the Sistine Chapel, one of Europe's most crowded tourist attractions. 

Sitting side by side in the square are 13th century dazzlers Palazzo del Popolo and Palazzo Capitano, two palaces that today act as the local history museum, full of relics of Todi of old. Beyond the square you'll find the Franciscan San Fortunato church. The imposing Gothic building has a campanile tower — climb to the top for a resplendent view of Todi, it's a relatively easy 153 steps up to see the cathedral and the 'Tempio' of Saint Mary of Consolation in the distance below. The 16th century Renaissance temple (it's a church) sits just outside the old town walls and looks modern by comparison to Todi's other buildings.

After sightseeing, take a stroll down Corso Cavour (full name Corso Camillo Benso Conte di Cavour on the map), the shopping street that's lined with independent, craft stores selling artisanal clothes, jewelry, and perfume — alongside barbers and grocers. As Todi is still very much lived in by a young population, you'll experience the energy of Italian daily life in the charming medieval piazzas.

This pint sized hamlet — it's just under a mile wide — is more than just a relic of civilizations that have come and gone. Todi's contemporary boutiques, excellent restaurants, and funky wine bars should ensure its place on your Umbria holiday destination hit list. It's a wine region and make no mistake — you'll see sweeping vistas of vineyards (and olive groves) with the Apennine mountains from many of the view points in hilltop Todi. 

The small 'osteria' restaurants are a great place to try the house wines. Quaint and snug Osteria Novecento is rated 4.5 on TripAdvisor, has a seasonal menu updated daily, and a range of vino to pair with every season. Fine dining La Cantina del Mercataccio is a special occasion spot that pours lovely local wines in a dining room that feels like an ancient stone cellar. But it's Michelin-listed Fiorfiore that's the one to make reservations for — housed in a villa with a charming patio surrounded by stunning views, its menu boats an impressive choice of wines from Todi and greater Umbria.

Among the largest wineries in all of Umbria, Cantina Tudernum is just 10 minutes drive north of Todi. This cooperative stocks niche bottles like Cervaro della Sala and local favorites Torracandia Sagrantino, Rojano Francore, and Grechetto Reserve. Grape enthusiasts note: September is harvest time in this lush area of Italy so it's the best time to visit if you want to see the harvest and production of these wines in action.