Travelers looking for natural beauty, rustic cuisine, and earthy, sun-kissed wines often head to the juggernaut that is Tuscany, but there’s a less tourist-trodden alternative. 

Umbria, Tuscany’s next-door neighbor, is just as beautiful, with dense forests and undulating valleys. Medieval hilltop towns and cities with ornate cathedrals and dramatic countryside views dot the landscape. The region’s steep and difficult-to-farm hillsides give Umbria a more ‘wild” feel than the rest of the country, and because the landlocked area surrounded by mountains has always been difficult to reach, it has had little outside influence. It’s thus often considered Italy’s most mysterious region and has stayed largely off travelers’ radars. 

However, with a slew of new castle and farmhouse hotels Umbria can no longer be ignored, and it feels more and more relevant as a destination as travelers increasingly seek meaningful vacations filled with culture, history, and the arts. 

Umbrians have a deep appreciation for music. One of the world’s most important jazz festivals has been held there annually since 1973. Umbrian “gold,” or extra virgin olive oil, makes up a small amount of Italian olive oil production but is exceptionally high quality. Typically made by families, it forms the basis for Umbria’s simple but delicious cuisine. Think plates piled high with salty prosciutto di Norcia, wild hare ragu, and truffles.

I have visited Tuscany more than half a dozen times. I’ve biked L’Eroica, have frequently visited the Uffizi in Florence, and stayed at many fabulous hotels, but the towns proclaimed Tuscany’s most beautiful often feel geared more towards tourists than locals. I’m increasingly venturing into Umbria in search of unspoiled landscapes and local flavor.

What to Do:

Covered with ancient oak forests, Umbria reportedly produces the most black truffles in Italy, and truffle hunting is an age-old family tradition. Umbria also produces prized white truffles, which hunters can find from November until January. Most hotels can arrange a truffle hunt, which happen in both summer and winter, but Wild Foods Italy offers a traditional truffle hunt experience in the mountain town of Pettino that includes truffle dogs, plenty of exercise, and a truffle feast featuring the days’ finds.

Every fall, the olive oil harvest is celebrated with the New Olive Oil Festival in October and November, where travelers are encouraged to visit olive oil mills in the region. They host art, music, and culinary events every weekend from October 19 to November 16. No matter when you visit, you can sample and purchase Umbria’s vibrant olive oil at places like Oleoteca Bartolomei in Orvieto. The family has been making olive oil since 1890, and you can visit the mill during the festival.

People have been making wine in Montefalco, the most lauded wine area in Umbria, since pre-Roman times. Go to taste Montefalco Sagrantino, a wine made of 100% Sagrantino grapes known for being structured and tannic. Because of this, they can age for decades and pair perfectly with Umbrian cuisine’s strong flavors. Orvieto produces excellent fruity but dry white wines made from Grechetto, Trebbiano, and other white grapes.

What to See:

Hilltop town hopping is a must in Umbria, and every visit should include a stop or stay in Perugia. The 14th-century city is the region’s capital and its beating heart. After winding through the more modern outskirts of town, you’ll find a well-preserved fortified city center at the top of the hill. Since it is also home to two universities it feels like a college town with large parks and plazas and a wide pedestrian-only street lined with shops and cafés, Corso Vannucci. Join the stylish Perugians sipping Aperol spritzes as the street comes alive in the early evening. Many landmarks are nearby: On Piazza IV November, find a Gothic cathedral with Renaissance paintings and frescoes, as well as Fontana Maggiore, a marble fountain that features carvings of biblical scenes and zodiac signs. The medieval Priori Palace nearby houses the Galleria Nazionale dell'Umbria, where many 13th century treasures are displayed.

Just 30 minutes southeast of Perugia, UNESCO-protected Assisi is famous for being Saint Francis of Assisi’s birthplace, one of Italy’s patron saints. The main draw may be the two-level Basilica of Saint Francis. You can visit the saint’s stone sarcophagus in the crypt and see the 13th-century frescoes tell Saint Francis’ life in the upper church. The works attributed to Giotto, Cimabue, and other notable artists are in bright tones of sepia, gold, and turquoise, which gives the church a warmer and more cheerful feeling than many Italian cathedrals.

Assisi is impressively perched on the slopes of Mount Subasio, and you can walk or drive all the way up to Rocca Maggiore castle. Saint Francis was the patron saint of the environment and wildlife and the Bosco di San Francesco is a public park and nature area near the basilica with wooded areas, olive groves, and ruins. Assisi also has Roman buildings, more impressive religious structures, beautiful fountains, and great shopping, including the art and concept shop A. Gallo (handmade watercolors here are made from Umbrian honey and rosemary essential oil) and a seemingly nameless shop selling traditional Umbria ceramics and décor at 45 A Via Fontebella. 

If you like cathedrals, the hilltop town of Orvieto is another must-see. The small, slow-paced city sits perched on the flat summit of a volcanic tuff and has an incredible underground cave network that showcases the city’s Etruscan history. The Duomo di Orvieto with a mosaic facade and striking black and white zebra-like stripes both on the outside walls and interior columns dates to 1290. Seek out the cliffside Pozzo di San Patrizio, a 16th-century well shaft with a double spiral staircase, for stunning views.

Where to Stay:

With medieval structures found throughout the region, it isn’t uncommon to find hotels in thousand-year-old buildings. However, thanks to restoration work and renovations, the interiors and amenities are anything but outdated — the best example may be Reschio in the Umbrian countryside.

After selling his successful publishing company in the ‘90s, Count Antonio Bolza bought the estate, which had abandoned farmhouses scattered throughout and a crumbling medieval fortress. His son Benedikt, an architect and designer, began renovating the historic farmhouses, and, along with his artist wife Nencia, he eventually opened a luxury hotel in the castle in 2020. A Michelin Three-Key designated property, every detail is aesthetically pleasing, from the Boot Room and floral studio that greets guests after they pass through the fortresses’ high gates to the brass and leather bar stools, designed by Benedikt, where guests sit while sipping white peach bellinis in the Palm Court Bar.

The Bolzas decorated guestrooms with a mix of custom-made and fine antique furnishings. The hotel is a haven for A-listers, a designer lovers’ dream, and a fantasyland for equine enthusiasts, as Spanish dressage horses are bred and trained on the property. Reschio’s first Yogherello retreat, which interweaves the art of yoga and watercolor painting, is from November 18 to 22, 2024. 

Perugia’s grande dame, the 5-star Sina Brufani, opened in 1884, and it’s still the stateliest address in the city. It’s located on Piazza Italia and has panoramic views of Umbria’s verdant valleys. Guests can stroll right onto Corso Vannucci and to sites like the cathedral, the Fontana Maggiore, and the National Gallery. The 94 rooms and suites are more classic than contemporary, furnished with antiques, shimmering drapes, and jewel-toned chairs. The hotel sits on the 3,000-year-old ruins of an Etruscan settlement ruins: The swimming pool, located under a medieval vaulted ceiling, has a transparent bottom through which you can view them.

Vocabolo Moscatelli opened in late 2023 and is a design hotel within the bones of a 12th-century monastery with a restored bell tower. Architects preserved original wood floors, wood-beamed ceilings, and terracotta brickwork but added contemporary touches such as a travertine swimming pool, glazed terracotta tiled bathrooms, and colorful outdoor furniture. The hotel, located near the hamlet of Calzolaro, feels like your own villa in the countryside, surrounded by wild lavender and olive trees. Vocabolo Moscatelli is essentially adults only, with only teens 14 and up allowed to stay overnight.

If your ideal Umbrian retreat is a farm stay, try Borgo della Marmota in Poreta. The owner turned a 17th-century hamlet into a rustic retreat with an outdoor pool and wellness offerings. Activities include truffle hunts, fly fishing, donkey rides to the top of the mountain above Poreta, and olive oil tastings. The hotel’s sister property, Villa della Genga, a one-time hunting lodge, has been producing olive oil since 1620. Tours and tastings can be arranged by appointment.

Where to Eat:

Follow one of the windy streets off Corso Vannucci in Perugia to reach the excellent traditional Umbrian restaurant La Taverna. Guests sit in a high-ceilinged dining room with a vaulted brick ceiling or on the patio to dine on handmade pasta like truffle ravioli and pappardelle with Umbrian ragu as well as grilled meats. 

Also in Perugia, Ada has earned a Michelin star for its flavorful meat and seafood dishes inspired by the region but refined by chef Ada Stifani. Diners can order dishes like red turnip dumplings with smoked eel and apple and lamb with dehydrated fruit as part of a tasting menu or a la carte. The wine selection is excellent.

Just outside of Perugia, Stella serves typical Umbrian country cuisine like pigeon stuffed with sausage and marjoram and fish from Lake Trasimeno in a bistro-style dining room. Desserts like panna cotta and Italian trifle are also a highlight. 

How to Get to Umbria:

Perugia is around a two-hour drive north of Rome. The city also has an international airport, Perugia San Francesco d’Assisi – Umbria International Airport, and flights are available from cities like Milan, London, and Brussels. It’s also possible to fly into Florence Airport, Peretola, but the drive to Perugia is about the same as from Rome. I recommend renting a car to explore Umbria: Towns have plenty of well-marked parking, giving you more flexibility to explore.

The Best Time to Go:

The best times to visit Umbria are during the shoulder seasons from April to June and September to October when there will be fewer tourists, but the weather is still reliable. In spring, visitors will be treated to fields of wildflowers, while in autumn, all of Umbria’s trees turn vibrant shades of burgundy, orange, and gold. While the temperature will be cooler, in November visitors can experience wine, olive oil and truffle festivals.

Combine It With:

Spend a few days exploring the many historic sights and museums of Rome, then unwind by escaping to the Umbrian countryside.

What to Know Before You Go:

- Umbria is relatively compact; you can see a lot in just three or four days.

- I visited Umbria with my family and found it very family-friendly. We broke up museum visits in Perugia with gelato stops on the piazza. Every hotel we stayed at had a beautiful pool, and we enjoyed activities like hiking and horseback riding.

- Umbria’s hilltop towns often have steep, windy streets, so pack comfortable shoes.

- If you don’t want to be turned away, wear clothing that covers your knees and shoulders when visiting cathedrals and religious buildings in Umbria.

- Mountainous Umbria can experience rain and thunderstorms in every season. Make sure to check the weather forecast and pack an umbrella.