Italy’s countryside is steeped in centuries of history, and its 20 distinct regions ensure that even a wrong turn can guide you towards something remarkable. When I crave a 21st-century time-travel experience, I prefer navigating Italy’s winding regional roads to the trains, as they lead to enchanting, hidden towns atop and beyond every hill. Here are five of my favorite discoveries from my journeys through this mesmerizing country.
Did someone say chess?? Yes! Marostica, in the Veneto valley, is the trifecta of chess, cherries and chocolate. Every even-numbered year, the charming medieval city hosts a living chess tournament in its main piazza, where players — pawns, bishops, kings, and queens — dress in early Renaissance costume to re-enact an epic poem based on Marostica’s 15th-century legend of two dueling families.
The Veneto was inspiration to Shakespeare and lately I think Marostica must have been the Bard’s source. Just a half hour northeast of Vicenza, Marostica is one of those picturesque towns still rocking its 15th-century heyday, with a fortress gate, looming castle, surrounding wall, and piazza-sized chessboard.
Every May, the town hosts a two-week-long cherry festival to celebrate the harvest — Marostica’s cherries are considered the best in Italy. If getting out of town is necessary, Marostica’s location is ideal for a whirl around the Veneto in search of Palladian villas in the areas surrounding Marostica, Vicenza, and Bassano del Grappa.
If Veneto is about castles, Umbria is about color. Its vivid natural palette has inspired almost every color pigment made; local artist Piero della Francesca immortalized its countryside. Forget about Assisi, Spoleto, Todi, and Orvieto, and head northeast from Perugia to Gubbio, a jewel-box medieval town.
High on the hill, Gubbio gives off an austere vibe with its monumental medieval architecture, such as the looming Palazzo dei Consoli and the Duomo. Don’t be daunted — Gubbio is a calm and almost meditative city, with wide-open piazzas, ancient Roman sites, and amazing century-old festivals. Gubbio has had a more than 500-year rivalry with Sansepolcro, hometown of della Francesca. Every year, top archers from both towns meet for the Palio della Balestra (alternately in each town), where archrivals vie for best bow. Everyone, and I mean everyone, from Sansepolcro and Gubbio is dressed in early Renaissance garb that some say is based on della Francesca figures.
On May 15, Gubbio strikes a pose as it celebrates patron saint Ubaldo in the Corsa dei Ceri, a race where three huge wooden candle-shaped columns are raced through the town in an all-day affair.
And if Gubbio is too sleepy for you, it’s easy to head out on the way of St. Francis, visiting Spoleto and Assisi, among other towns, or meander on the trail of Piero della Francesca paintings, which are found in churches and museums from Arezzo to Sansepolcro.
Civita di Bagnoregio, Lazio
Get lost on the way to Orvieto, look for Civita di Bagnoregio, which is in the northern edge of Lazio region. Thanks to its vertiginous isolation, Civita di Bagnoregio is a well-preserved medieval enclave of confusing alleys, surprise piazzas, and ivy-covered arches, and it’s practically all yours if you can make it up the steep, acrophobia-inspiring footbridge. The pedestrian-only town has as few as 12 inhabitants during the winter months.
Visit on a foggy morning, and you’ll see a town that looks like a small island floating in the clouds. Once the sun shines, you’ll find yourself face-to-face with a tiny stone town that sits precariously on a massive rock.
Civita di Bagnoregio feels figuratively and literally on edge, so it comes as no surprise that the World Monuments Fund placed Civita di Bagnoregio on its 100 Most Endangered Sites in 2006. Bagnoregio can be either a quick pit stop — within an hour you can scale the bridge, visit the town, and head back down — or, as I prefer, an overnight affair. Where else than an impenetrable town is better for a tryst?
Lately, Sicily has gotten a lot of love — and with good reason. It has the best of Italy: food, culture, archaeological sites, beaches. And Ortigia is its trophy. The tiny island off of Siracusa in Sicily’s southeastern corner is a Baroque sandcastle mixed with Greek mythology. Take a 10-minute walk around and you’ll see ancient Greek temples, a historic fish market, a fortress, medieval neighborhoods, and a piazza with even more ancient temples, outdoor cafés, and a Caravaggio painting.
Ortigia’s location is key: It’s immediately adjacent to Siracusa, a city whose archaeological treasures include a gorgeous Greek amphitheater. And it’s perfectly situated for day trips to Noto and Modica, two beautiful Baroque towns also noted for their sweets. Modica, in particular, is the center for Italy’s chocolate production.
Ceglie Messapica, Puglia
The Puglia region, in the heel of the boot, is a beautiful landscape of ancient farmhouses, coastlines, and castles. In Salento, the southern territory, sleepy Ceglie Messapica has reigned as “the center of Pugliese cuisine” for more than 90 years.
The 15th-century town, a cramped diamond in the rough with its castle and crooked cobblestone roads, is bursting with flavor and culinary tradition. The restaurant Cibus is the place to test out seasonal, time-tested recipes, and it has perhaps the stinkiest and most well-sourced cheese collection anywhere. Surrounding Ceglie is a countryside peppered with trulli, those charming conical stone huts that look similar to the Seven Dwarfs’ homes. Many of them have been converted into bed-and-breakfasts that are trulli scrumptious (sorry, couldn’t resist).
A version appeared on Yahoo Travel.