Most first trips to Italy include one or all of the country’s top five destinations: Rome, Florence, Venice, the Tuscan countryside, and the Amalfi Coast. It comes as no surprise that these five headliners top most bucket lists, as between them they cover the lion’s share of Italy’s artistic and architectural gems plus the country’s most iconic landscapes
Second trips, however, are where trip planning gets a little more interesting. Once the top sights have been duly checked off, you can dig a little deeper into the country’s 20 regions and veer off the “must-see” path. This is when we get to dig into our bag of tricks and suggest destinations clients may know much less about: Piedmont, for example, or the Ligurian Riviera, Puglia, and the Dolomites.
One of our favorite places to suggest for return travelers who want to experience stellar art and architecture, unforgettable food, postcard-perfect landscapes, and a relaxed, authentic vibe is Umbria. This region is set between Rome and Florence (it also works as an excellent stopover bookended by these two cities) and is known for its medieval hilltowns, including Assisi, birthplace of St. Francis of Assisi.
Here are some suggestions for what to see and do in Umbria taken directly from an email exchange we recently had with clients visiting in September if you’re looking for a unique destination but aren’t sure what Umbria has to offer.
We definitely suggest a trip into the region’s largest and most storied city. Since the historic center can be a bit impenetrable, we strongly recommend booking a guided walking tour to get the most out of your visit. Elisabetta, our favorite guide in Perugia, does a wonderful job of really making the city’s Etruscan and medieval history come to life. She often arranges visits to Perugia’s two hidden gems: the historic Moretti Caselli stained glass workshop and the Giuditta Brozzetti weaving atelier set in a 12th-century church, as well as other artisan and artist workshops plus gourmet chocolatiers (the city is known for its chocolate production).
Two of the most delightful small towns in Umbria are just minutes from one another and set in the heart of Umbria’s wine country. How we like to set up this day is a visit to one in the morning with lunch (we like to start in Montefalco because then you can have lunch in its postcard-perfect square at L’Alchimista, one of our favorite restaurants in Umbria). Afterward, you can stop at one of the many fantastic wineries in the area for a tasting and tour…flagship wineries Arnaldo Caprai and Paolo Bea offer a very sleek Napa-like experience though we usually go with the more rustic boutique wineries of Di Filippo and Romanelli. At Montioni, you can visit an olive oil mill and winery in one stop. Afterward, you can head to Bevagna for a stroll through town and an aperitivo in one of the many wine bars in town followed by dinner.
No visit to Umbria is complete without a stop in Assisi. The town is quite compact and easy to visit on your own unless you are particularly interested in art, in which case I suggest we book Elisabetta for insights into Giotto’s famed (and UNESCO-listed) fresco cycle in the Basilica of St. Francis. I also suggest a drive up the slopes of Mt. Subasio to St. Francis’ hermitage, where you can really feel the humble faith of this beloved figure. If you are interested in doing a cooking class while in Umbria, we can book you with lovely Letizia. Her farmhouse B&B is WAY up in the hills along a bumpy gravel road, but once you make it to the top, you are treated to one of the most stunning views over Assisi, the basilica, and the entire Umbrian valley from her terrace.
Umbria is a very food-focused region and some of its most treasured products include wine, olive oil, and truffles. We covered wine in Montefalco, but the area between Spello and Trevi is known for the latter two. A day exploring the delightful towns of Spello and Trevi with a stop at San Pietro a Pettine for a truffle hunt and lunch is one of the top options for what to see and do in Umbria. Spello has a beautiful (and steep) historic center and highlights include the Baglioni Chapel frescoed by Pinturicchio, a spectacular Roman mosaic unearthed just recently, and an authentic, small-town atmosphere. Trevi is even tinier and quieter than Spello, with very little tourism but beautiful views and a film-set-ready main square.
Cortona is located just across the Umbrian border and was made famous by “Under the Tuscan Sun”; you’ll immediately notice that you’re in Tuscany because the town is largely constructed from terracotta brick and dark grey stone rather than the pink and white stone for which Umbria is famous. The old town is compact and easy to explore on your own, and Tonino is a favorite local restaurant with a great terrace. Lake Trasimeno is a particularly beautiful spot at sunset…the prettiest town is Castiglione del Lago but those in the know head to San Feliciano or Passignano sul Trasimeno on the eastern shore to catch the sunset and have dinner.
Orvieto is set a bit off on its own, about an hour’s drive from the other towns in the central Umbrian valley. It’s famous for its spectacular Duomo, fabulous underground network of tunnels and caverns, and excellent local wines. We recommend a few hours in the city to explore and have lunch, then a stop at countryside winery for a tour and tasting before heading back to your base.
This archetypical medieval walled town represents Umbrian history in a nutshell. Its roots are steeped in the ancient Umbrii people (the town houses the most important example of the Umbrian language on the Eugubine Tablets in the Civic Museum), before passing through Roman civilization (there is a wonderful view of the town from the Roman Theatre in the valley below), and remaining architecturally frozen in the Middle Ages. Dine on truffles while you’re there and work off your hearty lunch with a climb (or cable car ride) to the top of Mount Ingino where you can visit the sanctuary dedicated to Gubbio’s patron saint and enjoy the amazing views from the Rocca fortress.
These are our top picks, but there are towns and attractions we didn’t list (Spoleto, the Nera River Valley, and Deruta for ceramics are the main omissions)!
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