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A Karen Brown Recommended Itinerary

Haunting Beauty of Umbria

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Tuscany is so popular that travelers frequently forget to visit Umbria, snuggled just "next door." Although similar in many ways to Tuscany, Umbria has its own haunting beauty and the advantage of fewer tourists. This is a region seeped in history and imbued with romantic charm. Here you find a beguiling landscape-a blend of rolling hills, craggy forests, rushing rivers, lush valleys, chestnut groves, and hillsides laced with vineyards. Adding further to Umbria's magic is that its hills and valleys radiate a soft mellow light, gleaming gently in the sun. It is not just the landscape that makes Umbria so delightful. It also has stunning medieval castles, incredible cathedrals, ancient monasteries, art treasures, fine wines, beautiful ceramics, and captivating towns perched on hilltops.

Recommended Pacing: You can conveniently follow this itinerary either before or after a tour of Tuscany. If you already have visited Tuscany on a previous trip to Italy, this itinerary stands alone. After the finishing the itinerary, you can loop back to Florence by heading north on the A1, or head south on the A1 to Rome. Whichever way you choose, in order to capture its beauty and many sightseeing possibilities, you need at least five nights in the Umbria region: We suggest three nights in the eastern part of Umbria. Choose a place to stay and in use it as a hub from which to journey out each day to explore a different sightseeing target. Next, loop south and choose a place to stay for two nights in the western part of Umbria, somewhere near Orvieto.


NOTE: This itinerary of Eastern Umbria is much too long for one day. Use it only as a framework for how the most interesting towns can be looped together. Once you choose which town you are going to use as the hub for your explorations, tailor the itinerary to visit the places mentioned in the itinerary that most appeal to you.

As you depart from Florence you are bound to run into a lot of traffic, but there are many signs to the expressway. Follow signs that lead to the A1 and take it south toward Rome.

Arezzo: About 65 kilometers after leaving Florence you come to a turnoff to Arezzo, located about 10 kilometers east of the highway. Arezzo is still in Tuscany, but since it is so close to Umbria and "on the way," now is the time for a visit. Arezzo has a rich history dating back to the Etruscan era, but is not as quaint as some of its smaller neighbors. It is well known as one of the largest gold centers in Europe and has many shops selling gold jewelry. Arezzo is also famous for its Antique Fair that is held in the Piazza Grande on the first Saturday and Sunday of every month. Here you find many unusual items such as antique coins, jewelry, furniture, stained glass remnants, paintings, light fixtures, handmade linens, pottery, trunks, etc. The fair is considered one of the most important ones in Italy and so popular that people come from far and near to browse the rich collection of antiques. Arezzo was the birthplace of Guido Monaco who around the year 1000 A.D. devised musical notes and scales. One of Arrezo's famous inhabitants was the powerful 14th-century poet Pietro Aretino who took great glee in writing scandalous poetry about the rich and famous. Aretino's greatest skill was gentle blackmail, extorting great sums from princes and popes who paid him not to expose their indiscretions in poetry.

Cortona: From Arezzo follow S71 south to Cortona, a gem of a walled town terraced up a steep hillside covered with olive trees and vineyards. Like Arezzo, Cortona is still in Tuscany, but fits more conveniently into the itinerary for Umbria since it is on the route. Stop to enjoy the atmosphere of this medieval town: its narrow, twisting, cobbled streets, jumble of small squares, lovely boutiques, excellent restaurants, and colorful buildings are delightful. The heart of the town is the Piazza della Repubblica, the main square, which has many narrow streets feeding into it. If you are up for walking, climb the twisting streets to the old fortress standing guard over the town.

Lake Trasimeno: Leaving Cortona, continue driving south on S71 toward Lake Trasimeno. In about 11 kilometers you come to a four-lane expressway. Do not get on the highway, but instead continue south on S71, which traces the west shore of Lake Trasimeno, Italy's fourth largest lake, which is fed by underground channels linked to the Tiber river basin. Fascinatingly, the early Romans built these underground waterways many centuries ago. Follow the road south for 9 kilometers to Castiglione del Lago, the most interesting town on the lake. Built on a high rocky promontory that juts out into the water, the old walled city with its battlements and towers has lots of character. Artifacts and tombs nearby indicate it was originally an Etruscan settlement, but what you see today dates from the Middle Ages. In the 1500s it was the dukedom of the Corgna. In the church of Santa Maria Maddalena you can see a 16th-century panel with paintings of the Madonna and Child by Eusebio da San Giorgio. Also visit the Palazzo del Capitano del Popolo, the Palazzo della Cornna, and the Leone fortress.

Umbertide: Continue the loop around the lake then take the road toward Magione, which is just before the junction with the expressway heading to Perugia. In a few minutes, you see the four-lane expressway, but do not get on it. Instead, continue over the highway and follow the back roads through the countryside to Umbertide. Stop for a short visit to this small, 10th-century town that hugs the banks of the Tevere River. In addition to the castle, you might want to visit the Church of Santa Maria della Reggia, which is an intriguing octagonal, three-tired building topped by a cupola. Another church, the Holy Cross, is famous for its lovely painting by Signorelli, called Deposition from the Cross.

Gubbio: Leaving Umbertide, take the road that passes over the highway E45 and continue on to Gubbio. This splendidly preserved, medieval walled town is perched high on the slopes of Monte Ingino. The setting is superb and the view from the plaza that sits like a shelf overlooking the countryside is breathtaking. The narrow, cobbled streets and walkways lacing the hillside are delightful to explore. The town is filled with architectural masterpieces, one of these, the Basilica, dominates the town. There is much to see including the Cathedral, the Consuls Palace, the Piazza Pensile, the Pretorio Palace, and the Santa Maria Nuova church where you can see Ottaviano Nelli's Madonna del Belvedere. Outside the city walls, nestled below the town, there are the remains of a Roman theater-another reminder of how important the city was in its prime.

Perugia: From Gubbio head south on S298 in the direction of Perugia. There is a turnoff to Perugia, which is surrounded by many modern commercial buildings. If time is short, bypass Perugia (which is not as pristine as many of Umbria's other jewels) and continue on to the junction of S75 and continue east following signs to Assisi. However, if you want to "see it all," Perugia is rich in history and has many delights. Perugia is a large medieval city surrounded by ramparts. An important Umbrian city since Etruscan days, the old town has at its heart the Piazza IV Novembre, a beautiful square with an appealing fountain, the Fontana Maggiore, built in the late 13th century.

Assisi: Coming from either Perugia or Gubbio, take S75 east following signs for Assisi, one of our favorite targets in Umbria. Built up the steep slopes of Mount Subasio, this magical city is a tribute to St. Francis. Although he was born into a family of wealth, after several visions in which Christ appeared to him, St. Francis left his privileged life. He was obviously a person with a deeply poetic soul and his tender teachings of reverence for the beauties of nature and kindness to all animals and birds still appeal to us today. To remember your visit, you might want to buy a statue of St. Francis to bring home. You will find statues in all sizes and price ranges in the many shops.

Even if it were not for the lingering memory of the gentle St. Francis, Assisi would be a "must see" for it is one of the most spectacular hill towns in Umbria. Perhaps there are a few too many souvenir shops, but this is a small price to pay for the privilege of experiencing such a very special place. The town walls begin on the valley floor and completely enclose the city as it climbs the steep hillside to the enormous castle at its summit. Assisi with its maze of tiny streets is a marvelous town for walking (you must wear sturdy shoes) and it is great fun as you come across intriguing little lanes opening into small squares. When you stop to rest, there are breathtaking vistas of the lovely Umbrian fields stretching out below. Along with many other historic buildings, Assisi's most famous monument, St. Francis’ Basilica, was severely damaged by an earthquake in September 1997. However, all of the repairs have now been completed and the town looks remarkably "back to normal." The basilica, which also houses a monastery, faces onto a large square bound by columns forming vaulted covered walkways. In addition to the monastery, there are two basilicas-upper and lower. Both are adorned with excellent frescoes that were unfortunately damaged by the earthquake. Also while in Assisi, visit Santa Chiara (St. Clara's Church). Clara, a close friend of St. Francis, founded the Order of St. Clares. Go into the church to view the lovely frescoes of Santa Clara and her sisters. Part of the enjoyment of Assisi is just to stroll through its narrow, cobbled streets-the whole town is like a living museum. If you have time, hike up to the Rocca Medioevale, an enormous 14th-century fortress perched on the hillside overlooking the city. From here you have a magnificent bird's-eye view of Assisi and beyond to the enchanting Umbrian countryside sweeping out to the distant hills.

Collepino: From Assisi you can continue on the S75 in the direction of Foligno. However, if you feel adventuresome and enjoy getting off the beaten path, there is a narrow, twisting, very scenic back road that leads through the hills making a loop from Assisi that ends up back on the S75 in Spello, about 5 kilometers before Foligno. The driving is difficult, but you can enjoy the beauty of the rugged forested mountains, an area of Umbria seldom seen by tourists. The road begins at the upper part of Assisi. Follow signs in the direction of Gualdo Tadino, but before you get there, take the road marked to Armenzano where you continue on following signs to Spello. After going through Armenzano, the road passes the adorable secluded hamlet of Collepino, which oozes charm with its winding cobbled streets and stone houses.  It is so tiny that you quickly see it all. After Collepino, it is 7 kilometers on to Spello, where the road joins the S75, which you take going south.

Bevagna: Five kilometers south of Spello you come to Foligno where we suggest leaving the S75 and taking instead the back roads that to enjoy the lovely villages and scenery. From Foligno S316 toward Bevagna, which you reach after about 8 kilometers. Bevagna is an enticing, intimate, charming walled village, founded by the Romans. In addition to just enjoying the allure of the town, there is much to see including a stunning 19th-century opera house, the beautiful San Michele church, well-preserved mosaics in the old Roman baths, and a paper press making paper just as it has been for centuries. If it is mealtime, there is a wonderful place for lunch, L'Orto degli Angeli.

Montefalco: From Bevagna, take the road marked to Montefalco (located 7 kilometers from Bevagna). Montefalco is a walled town that crowns a hill with sweeping views of the Umbrian countryside. The town is a maze of small, narrow streets. For sightseeing, the main attraction is San Francisco, a church now converted into a museum that displays some of the finest work of Benozzo Gozzoli, including the fresco Life of St. Francis. Also, a delicious wine, Sagrantino, is produced here.

Spoleto: From Montefalco, loop back to the main road, S75, and continue south following signs to Spoleto. Not only is medieval Spoleto dramatically perched atop a hill, but it also has an almost unbelievable bridge dating from Roman times. This Ponte delle Torri, spanning the deep ravine between Spoleto and the adjoining mountain, was built over an aqueduct existing in the 14th century. This incredible engineering wonder is 230 meters long and soars 81 meters high. It is supported by a series of ten Gothic arches and has a fort at the far end as well as a balcony in the center. The 12th-century Cathedral in Spoleto is also so lovely that it alone would make a stop in this charming town worth a detour. The exterior of this very old cathedral, with its beautiful rose window and intricate mosaics, is truly charming. Although a great sightseeing destination at any time of the year, Spoleto is very popular in late June and early July when it hosts the world-famous Spoleto Festival, featuring great music, dance, and theater. During the festival season rooms are usually more expensive and almost impossible to secure so should be booked far in advance.

Torgiano: Torgiano, in the center of a rich wine region, has a lovely small wine museum. You would never dream that such a tiny town could boast such a gem, but it is not a coincidence: the Lungarotti family owns the vineyards for many kilometers in every direction. Signor Lungarotti furnished the museum with artifacts pertaining to every aspect of wine production from the earliest days, creating an interesting and beautifully displayed collection worthy of a detour by anyone interested in wines. In the center of town, the Lungarotti family owns, Le Tre Vaselle, a charming choice for lunch.


From Spoleto, a scenic route connecting the eastern part of Umbria to the western part of Umbria is to take the S418, which twists west from Spoleto for 25 kilometers through beautiful hills to the E45. Turn north on E45 for about 21 kilometers and turn west on S448, following signs to the A1 and Orvieto.

Todi: The picture-perfect village of Todi makes a great midway stop between Spoleto and Orvieto. It is located near the junction of E45 and S448 and is well signposted. This adorable small town crowning a hilltop like icing on a cake is one of our favorites. No, there isn't much to see-it is the town itself that is so picturesque. It is just fun to wander the twisting cobblestone streets, enjoy the medieval ambiance, and stop to enjoy a cappuccino in one of the sidewalk cafés. As you stroll through the small village, watch for the Cathedral, the People's Square, the intimate San Ilario Church, and the Roman/Etruscan Museum.

When you come to the A1, don't get onto the freeway, but instead follow signs to Orvieto. NOTE: When deciding on a town in the area to use as a hub for sightseeing don't limit your choice to those in Umbria. You will also find a rich selection of places to stay very nearby in Tuscany and Lazio.

Orvieto: Originally founded by the Etruscans, Orvieto later became a prosperous Roman city, famous for its production of ceramics. Orvieto is spread across the top of a hill that drops down on every side in steep volcanic cliffs to the Umbrian plain 200 meters below-you wonder how the town could ever have been built! Drive as far as you can up to the town, park your car, and proceed on foot. Have a good map handy because you pass so many churches and squares that it is difficult to orient yourself-Orvieto is a maze of tiny piazzas and narrow twisting streets. Continue on to Orvieto's center where a glorious Duomo dominates the immense piazza. You may think you have seen sufficient stunning cathedrals to last a lifetime, but just wait-Orvieto's is truly special, one of the finest examples of Romanesque-Gothic architecture in Italy. It is brilliantly embellished with intricate mosaic designs and accented by lacy slender spires stretching gracefully into the sky. Within the Duomo, you absolutely must not miss the Chapel of San Brizio; here you find frescos by Fra Angelico and Luca Signorelli.  Also of interest in Orvieto is St. Patrick’s Well, hewn out of solid volcanic rock. Pope Clement VII took refuge in Orvieto in 1527 and to ensure the town's water supply in case of siege, he ordered the digging of this 62-meter-deep well. It is unique for the 70 windows that illuminate it and the two spiral staircases that wind up and down without meeting. Other sights to see include the Papal Palace, the Town Hall, and the archaeological museum.

Civita di Bagnoregio: Although Civita di Bagnorégio is not in Umbria, it's located just southwest of Orvieto, so it conveniently ties in with this itinerary. If you are a photographer and love picturesque walled villages, few can surpass the setting of this small town. Take the N71, which twists west from Orvieto toward Lake Bolsena. Stay on N71 for about 20 kilometers and then turn left heading to Bagnorégio. Go into town and follow signs to Civita, which crowns the top of a steep, circular-shaped, rocky outcrop. There is no road into the village-the only access is by walking over a long, narrow suspension bridge that joins the two sides of a deep ravine. Once you arrive, you will find a few shops, some Etruscan artifacts, a church, and a restaurant. However, the main focus is the town itself with its narrow arcaded alleyways and a dramatic 180-degree view of the desolate, rocky canyons that stretch out around the town with a haunting beauty.

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A Few Nearby Hotels and Bed & Breakfasts:   List Them All

A Karen Brown Recommended Hotel / Inn Montorio
Montepulciano, Tuscany, Italy
A Karen Brown Reader Discovery Aldrovandi Palace Villa Borghese
Rome, Lazio, Italy
A Karen Brown Reader Discovery Villa Torre Rossa Apartments
Florence, Tuscany, Italy
€ 100-240
A Karen Brown Reader Discovery Agriturismo Terrapille
Pienza, Tuscany, Italy
A Karen Brown Reader Discovery Villa LeMura
Panicale, Umbria, Italy

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[ icon ] Terni
Umbria, Italy
[ icon ] Asciano
Tuscany, Italy
[ icon ] Montepulciano
Tuscany, Italy
[ icon ] Monticchiello
Tuscany, Italy
[ icon ] Greccio
Lazio, Italy

A Few Nearby Restaurants:   List Them All

[ icon ] Le Radici Natura & Benessere
San Casciano dei Bagni, Tuscany, Italy
Italian Cuisine
[ icon ] Picchio Verde
Gubbio, Umbria, Italy
Italian Cuisine
[ icon ] Relais del Colle
Ripatransone, Marches, Italy
Italian Cuisine
[ icon ] La Capannina
San Donato in Poggio, Tuscany, Italy
Italian Cuisine
[ icon ] Enoteca Oberdan
Todi, Umbria, Italy
Italian Cuisine
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