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Umbria: Insider’s Guide

by Maria Gabriella Landers and Brian Dore | December 17, 2014

The insider advice on this page is from two of Wendy’s Trusted Travel Experts for Italy: Maria Gabriella Landers and Brian Dore of CIU Travel.

Trusted Travel Expert
Maria Gabriella Landers and Brian Dore

Opera singers who divide their time between Italy and the United States, husband-and-wife team Brian and Maria Gabriella design imaginative itineraries throughout Italy that focus primarily on gastronomy, art, architecture, archaeology, and history; they can also help with side trips into Switzerland. Maria Gabriella, who has a background in art history as well as opera, is an ambassador of Italian culture for Perugia’s Università per Stranieri. Brian, a former chef, worked at several New York restaurants before embarking on an international career as an operatic baritone, now an occasional side gig; he’s also an enthusiastic hiker and skier who’s tested out many slopes and trails in the Alps. Together with their team of charming and terrifically knowledgeable guides and drivers, Maria Gabriella and Brian give their clients an intimate experience no matter where they go, from Rome’s most iconic landmarks to the hidden-treasure hill towns of Tuscany to Switzerland’s cultural capitals and charming mountainside villages.

Trips start at $1,000 per day for two travelers in low season or $1,500 in high season, with a three-night minimum.

Where to Stay and Eat

Best bang-for-your-buck hotel
Compared to neighboring Tuscany, Umbria is significantly less expensive. Even the most elegant hotels are a good value, and you can often splurge on a larger room or suite for the same amount of money that a much smaller accommodation would cost just an hour’s drive away. We love Bevagna’s L’Orto degli Angeli, a historic palazzo with frescoed ceilings and an excellent restaurant, which is walking distance to the town’s main piazza, shops, and sights.

Restaurants the locals love
Ask anyone who appreciates food and wine in Umbria, and they will all send you to the same place: L’Alchimista in Montefalco’s pretty main piazza. Despite its memorable food, extensive wine list, Italian mamma who comes out of the kitchen periodically to check on diners, and incredible popularity (reservations are a must in high season), this casual trattoria hasn’t upped its prices in years, making it quite possibly the best value north of Rome. The dish you’ll still be thinking about six months later? Gnocchi al Sagrantino, potato dumplings cooked in the town’s beloved wine.

In Perugia, tables at the historic Da Cesarino are always crowded with local politicians and personalities sitting alongside students and travelers. The fare is solid and classic, and in summer, you can sit outside to take in the view of the town’s iconic fountain (though locals mostly choose inside tables, preferring to eat in privacy). The service is of the Italian no-nonsense variety, but for the most authentic dining experience in Perugia, there is no better place.

Must-have dishes
Strangozzi, a thick, long, and decidedly filling pasta, served with a pungent game sauce or aromatic local black truffles; salty prosciutto from Norcia; heirloom legumes including Castelluccio’s lentils and Lake Trasimeno’s fagiolina; foraged treasures such as mushrooms and wild asparagus (delicious in an egg frittata); and, of course, local olive oil over everything.

Must-have wine
The tannic, tongue-tingling Sagrantino di Montefalco red.

Meal worth the splurge
Your most memorable meals here are more likely to be had at the simple, family-run trattorias rather than the elegant gourmet destinations, but there are a couple of exceptions worth the investment—namely, Foligno’s Villa Roncalli or celebrity chef Gianfranco Vissani’s eponymous restaurant in Baschi.

Prime picnic spot
Most of Umbria’s towns are so tiny that you need only step out of the medieval city gates to come across a quiet park or olive grove where you can spread out a blanket and enjoy your local fare with a view. An exception is the cosmopolitan capital city of Perugia, where the locals are elegantly turned out, the smart sidewalk cafes are abuzz, and the boutique-lined streets are devoid of grassy spots. For a quiet respite here, try the welcoming lawns in front of San Michele Archangelo (at the end of Via Garibaldi) and San Francesco al Prato (at the end of Via dei Priori), or settle into a bench in Giardini Carducci (in front of the Brufani Palace hotel) for great views and people watching.

Assisi frowns on picnicking in the public piazzas, especially the few grassy squares in front of the town’s churches (the expanse in front of the Basilica’s upper church is fenced off for this reason). For a sandwich with a view, you can hike up to the dramatic Rocca Maggiore fortress, where there is a hillside beyond the castle walls that captures views over Assisi and the Umbrian valley; or stay inside the castle courtyard on windy days.

What to See and Do

Don’t miss
The smaller villages such as Montefalco, Spello, Assisi, Spoleto, Gubbio, Orvieto, or Bevagna. Just because they often merit only a sentence or two in the travel guides doesn’t mean they aren’t worth a visit. Bevagna, for example, has a number of lovely Romanesque churches, a Roman mosaic, a Hollywood set–ready piazza, and a plethora of excellent, casual trattorias. Montefalco, perched high above the Umbrian plain, has one of the most dramatic views around and a surprisingly wonderful museum—the Museo di San Francesco, the former church of Saint Francis—with important works by Benozzo Gozzoli and Perugino. A good rule for Umbria: The smaller the font on the map, the more likely you are in for a lovely surprise.

Don’t bother
About 20 years ago, Todi was named a model sustainable city by an American professor of architecture, an honor quickly transformed into “the world’s most livable city” by the U.S. press. Almost overnight, a wave of foreigners descended on this once-sleepy hill town to enjoy its bucolic blandness. We have nothing against Todi, but its reputation and draw are disproportionate to its actual charm or importance. It has a church or two, a relatively pretty piazza, and a nice view, but so do a number of infinitely more interesting and lovely hill towns in Umbria (see “Don’t Miss,”).


Casteluccio Piano Grande. Photo by Brian Dore.

Casteluccio Piano Grande. Photo by Brian Dore.

Hidden gem
The remote Piano Grande, a high mountain plateau in the Sibilline National Park, straddling the border between Umbria and Le Marche. The scenery here is otherworldly—especially in spring when the entire plain is in flower, and the tiny village of Casteluccio perches above the morning mist like a scene from Middle-earth. Stop here (or in Norcia, in the valley below) to stock up on the area’s famous lentils, truffles, sheep cheese, and wild boar charcuterie.

In Assisi, you can leave the crowds behind by deviating a few hundred meters off the pilgrim track. While most visitors head directly to the iconic Basilica of San Francesco, for a real taste of the quiet humility of this fascinating historical and religious figure, visit instead the simple, 12th-century monastery at San Damiano, just outside the center of town. This is where Francis famously received the call to restore the Church, and where his faithful friend and ally Claire founded the Poor Claires and eventually died.

Cheap thrill
For a beautiful walk virtually steps from town, the new Bosco di San Francesco in Assisi is a reclaimed woodland next to the Basilica of Saint Francis. Hand over the nominal donation (the site is owned by Italy’s National Trust), then take the pretty path down the hillside behind the basilica to the restored monastery below, stopping at the benches along the route to soak in the silent woods and lovely views; cross a medieval bridge to follow the final leg of the trail, running alongside the bubbling Tescio River at the valley floor; then double back to stop at Osteria del Mulino, an old mill, for a simple meal.


Norcia. Photo by Brian Dore

Norcia. Photo by Brian Dore

How to spend a Sunday
Sunday is the day in which the primary—if not sole—activity in Umbria is centered around a leisurely meal that takes the better part of the morning to prepare and most of the afternoon to consume. We suggest taking a long drive in the country, stopping at a remote agriturismo, lingering over lunch until the late afternoon, and then walking it off down a scenic country lane. Some of our favorite options are Locanda de Senari, a family-run place in Castelluccio di Norcia that serves incredible, house-made cured meats, cheeses, and pasta; Agriturismo Bartoli, a working farm and truffle reserve in the hills above Spoleto; and Agriturismo Camiano Piccolo, just outside Montefalco.

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Best Times to Go

For much of the year, Umbria displays a general air of muted contemplation, a symptom of the many centuries the region spent under Papal rule. But that goes out the window come festival season (which peaks in May, June, and September), when the reserved Umbrians really let down their hair. These small but rollicking historical and religious celebrations—not the bigger ones choreographed for foreign tourists—involve entire communities, from the ladies decorating the streets to the smallest children dressed in Medieval garb. We especially love Gubbio’s Corsa dei Ceri in May, Bevagna’s Mercato delle Gaite in June, and Foligno’s Quintana in September.

Worst Times to Go

Umbria is known as Italy’s green heart: Gorgeously lush much of the year, the area is covered with rolling hills kept verdant by winter rains. If you visit during January and February, you’ll likely spend your days dashing in and out of the wet and your evenings huddled next to a fire, fighting off the cold that permeates the region’s Medieval castles and historic villas.

Biggest Rookie Mistake

Want to get an Umbrian riled up? Mistake their hometown for a Tuscan city. (They’re too polite to say anything to your face, but they’ll quietly exude disdain). Umbria is a region all its own, with a distinctive history, culture, cuisine, architecture, and accent. And unlike its more famous neighbor, Umbria still has countless authentic corners where not everything is geared toward tourism and English is not so ubiquitously spoken.

Bragging Rights

For wine aficionados and collectors, a private wine tasting with owner Roberto at Spello’s Enoteca Properzio is a must; Roberto has personal relationships with the producers of many of the country’s finest wines, from famous names to tiny organic producers, so he can fill you in on all aspects of the Italian wine world. We can also arrange a private cooking class in a farmhouse so stunning that it’s been featured in several design magazines and where the owner—a great cook and hostess, not to mention a well-respected attorney—will teach you to use some of the region’s most humble ingredients to prepare an unforgettable meal.

Word of Warning

A number of Italy’s most iconic food products have weathered scandals as of late—fake truffles from China, counterfeit wine—though Umbria’s production is so limited and local that you are unlikely to get anything of less-than-excellent quality, especially when purchasing treats like olive oil and wine directly from the producer. We do recommend against purchasing flavored truffle oil, though, which is often chemically enhanced.

Don’t Forget To Pack

You want to be chic to fit in with the fashion-conscious Italians, we know. But Umbria is not the region for stylish heels or ballet flats. You’ll be doing a lot of walking in these towns—much of it on steep, cobblestone lanes—so opt for the most comfortable walking shoes you have during the day. And if you’re planning on visiting olive mills, cheese farms, or any other sort of agricultural area, it’s a good idea to throw in an inexpensive pair of wellies.

Perfect Souvenir

Umbria is a region of small, historic, family-run workshops, for anything from shoes to fine linens to hand-painted ceramics to organic olive oil. We all want our souvenirs to have a story, and here you will likely meet and chat with the very person who has crafted what you will be tucking into your suitcase. Deruta and Gubbio are historic centers for ceramics; Montefalco and Perugia produce traditional jacquard linens in cotton, silk, and wool; and the most prized olive oil comes from the mountain slopes between Spello and Spoleto.


Instagram Moment

Montefalco’s Piazza Belvedere at sunset—while gazing out across the valley at the flickering lights of Assisi, Spello, and Trevi, you’ll understand why this town is known as the Ringhiera dell’Umbria, or the balcony of Umbria.

The scenic overlook in Perugia’s Giardini Carducci, with the bell towers of San Domenico, San Pietro and, in the distance, Assisi’s San Francesco spread out before you.


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