Italy: Umbria & Assisi

You are met at the Orvieto train station and transferred the short distance up to the medieval city situated on a plateau above steep cliffs made of volcanic tufa stone. Orvieto floats almost like an island over the Umbrian countryside of olive groves and vineyards. Compact and easy to navigate, the city’s historical center is a perfect introduction to Umbria—it has been inhabited for millennia, from the Etruscan period through its Roman conquest, and centuries later gained prominence in the Middle Ages. A stroll through the charming pedestrian center begins at its striking 13th-century cathedral with gold facade and striped walls. Orvieto also features fascinating subterranean sites—a network of caves and tunnels used in times of siege or for storing wine, as well as the Pozzo di San Patrizio—St. Patrick’s Well—all built in the 16th century. You can peruse the region’s distinctive painted ceramics in the many shops, perhaps while enjoying a delicious cone of gelato. Later, to accompany dinner, you may enjoy a glass of Orvieto—the dry or semi-sweet white wine that shares the city’s name, produced from grapes grown on surrounding hillsides.

Overnight in Orvieto

5.2 or 9.8 miles, easy to moderate, 1,300-ft. elevation loss and 500-ft. elevation gain

After breakfast, a 30-minute drive takes you through the rolling Umbrian countryside with views back to Orvieto to the start of the day’s walk in the Area Attrezzata Sette Frati, located in the Monte Peglia Natural Park. The full day’s walk gently descends over a well-signed and maintained gravel track through a tranquil landscape, alternating between typical Mediterranean forest of holm oak and low shrubs, such as broom and blackberries, cultivated fields, and open meadows with abandoned farmhouses—a perfect setting for a picnic lunch. You soon understand Umbria’s nickname as the “green heart of Italy” before a final ascent delivers you to your home for the next two nights—a secluded hilltop country farmhouse with panoramic valley views. Dinner tonight is on site at the farm’s warm wood-beamed restaurant.

Overnight in Monte Castello di Vibio

6.2 miles, easy to moderate, 500-ft. elevation gain and loss

This morning, you depart the hotel for the day’s destination of the medieval hamlet of Titignano. Today this village is a sprawling estate featuring a 12th-century castle, winery, and farm buildings—all gathered around a central square with sweeping views of Lake Corbara. Created by a hydroelectric dam on the Tiber River, Lake Corbara is a scenic rural reservoir; surrounding it are acclaimed vineyards producing DOC-certified red wine. In this region, much of the landscape is of cultural and natural significance, including the Tiber river basin, nearby lakes, and many towns. Habitats for migratory and resident birds share space with the archaeological remains of Etruscan and Roman civilizations, as well as medieval castles and ruins. Your walk starts on a paved, low-traffic country road and continues onto a mix of gravel roads and grassy trails through the Umbrian countryside. Enjoy views of beautiful fields dotted with villas and deep oak forest, as well as the distant hill town of Todi before reaching the piazza of Titignano. Here, enjoy gorgeous vistas over expansive vineyards and down to Lake Corbara. You are then welcomed to lunch accompanied by the property’s renowned wine—produced in the surrounding hillsides. An afternoon transfer returns you to Podere le Corone where there is time to enjoy the seasonal outdoor pool or simply relax enjoying the views before dinner once again in the hotel’s dining room. For an additional, optional walk before or after dinner, amble to the neighboring town of Doglio, a tiny village with sweeping panoramas of the surrounding valley.

Overnight in Monte Castello di Vibio

6.8 miles, easy to moderate, 200-ft. elevation gain and 750-ft. elevation loss

Today, experience a trio of medieval hilltop towns as you stroll through the pastoral countryside of the Tiber Valley. This morning, you transfer approximately 20 minutes to the tiny fortified village of Monte Castello di Vibio, described by the 16th-century architect and painter Cipriano Picolpass as “an ideal life.” Here, you have time to explore the main piazza, with its panoramic views and Baroque church, the crenulated tower of Portia di Maggio, the defensive walls, and the diminutive Teatro dell Concordia—with only 99 seats, billed as the smallest theater in the world. After strolling the ancient stone streets of this perfectly preserved town—perhaps stopping at a local bar for a coffee or the village grocer to pick up picnic supplies—you set off into the countryside, enjoying sweeping views across the Tiber Valley. Descending through olive groves and vineyards, your route passes by the Rocca di Cecanibbi, a medieval watchtower, before you arrive in the small, fortified hamlet of Cecanibbi, a cluster of stone houses clinging to the walls of a massive medieval castello. The final section of today’s walk is along the Tiber River, used by the Romans to sail wine and olive oil to Rome. At the walk’s end, your driver meets you and brings you to Montefalco, known as “the balcony of Umbria” for its dramatic hilltop perch. With its five gates and five-sided piazza, this medieval town is renowned for its DOCG wine, Sagrantino, traditional linen, and Saint Francis Museum, which contains art work and frescoes depicting the saint, including “Scenes from the Life of Saint Francis” by Florentine Renaissance painter Benozzo Gozzoli. Following an optional visit to the Antonelli San Marco Winery for a tasting of their excellent wines, including Sagrantino di Montefalco DOCG, take time to amble through Montefalco’s cobblestone streets before transferring onward to the beautiful walled town of Spoleto, your home for the next two nights. Built at the head of a wide valley, Spoleto spills over a hillside, with its main sights concentrated in the compact upper town. After settling in your hotel, take time to stroll out this evening, perhaps over the 14th-century Ponte delle Torri (Bridge of Towers), for a wonderful overview of the region.

Overnight in Spoleto

8 miles, easy to moderate, 900-ft. elevation gain and 2,200-ft. elevation loss

This morning, a short taxi transfer delivers you up to the neighboring peaceful resort village of Monteluco—home to a convent established by St. Francis in the 13th century and nearby Bosco Sacro (Holy Wood). Following an exploratory wander, you enter the wooded slopes of Monteluco, held sacred by the Romans and medieval Christians, including St. Francis who was fond of meditating here. A gentle ascent along the Via di Francesco (also known as the Via di Roma)—the road along which St. Francis walked the hundreds of miles to Rome—leads you to the summit and fork of Castelmonte for panoramic views of the mountainous Valnerina river valley. Following a descent through the forest along the medieval aqueduct, take in spectacular views of the Ponte delle Torri before meandering back into town. This afternoon there may be time to visit Spoleto’s many sights and simply absorb its special atmosphere; a busy place during the festival, it is relatively uncrowded at other times of the year. Its 14th-century defensive castle, the Rocca Albornoziana—now an interesting museum—presiding from the town’s highest point, was built on the site of a Roman acropolis. The delicate pink-stone main cathedral, the Duomo of Spoleto, dating from the 12th century, was built on the site of an early Christian temple and features stunning Renaissance frescoes by Florentine artist Filippo Lippi. You may also choose to visit the Casa Romana museum, believed to have been the house of the Emperor Vespasian’s mother, and the Roman Theater, still used for performances during the Festival of the Two Worlds, held annually over 17 days in late June and early July. Other active options are also available in Spoleto and environs, such as horseback riding or bicycling (payable locally).

Overnight in Spoleto

7.7 miles, easy to moderate, 1,450-ft. elevation gain and 1,000-ft. elevation loss

This morning, a transfer takes you through the heart of Umbria to the start of the day’s walk at Valfabrica. Today you follow the historical route known as the Franciscan Trail, the route by which St. Francis was brought back to Assisi when he was found seriously ill by a group of horsemen. The terrain is gently undulating—alternating between oak forest and open pasture, interrupted by old stone farmhouses and parish churches, dovecotes, and crumbling fortress towers on prominences above. The final portion rising to the Basilica of Assisi is steep but short, and while challenging, it is exhilarating to arrive on foot in the city that is a spiritual destination for many and also a UNESCO World Heritage site. You continue on foot to your hotel in the historical center, just around the corner from the Roman Temple of Minerva, now the Renaissance church of Santa Maria sopra Minerva, and the Basilica of St. Clare, built in the 13th century for St. Clare of Assisi, the founder of the Order of Saint Clare.

Overnight in Assisi

10 miles, easy to moderate, 500-ft. elevation gain and 3,700-ft. elevation loss OR 5.3 miles, easy to moderate, 1,200-ft. elevation loss

After breakfast, there is a short transfer to the Natural Park of Mount Subasio, a protected area with serene paths meandering through open meadows as well as oak and pine forest. Mount Subasio is the sprawling mountain on whose flank Assisi is built. A haven of subtle beauty and spirituality, it was here that St. Francis prayed and communed with the birds, all gathered on tree branches (there is an option to stop en route to your walk at the Eremo delle Carceri—the famous hermitage of St. Francis). Hiking in the meadows along the summit of the mountain, you are likely to see grazing herds of sheep, white Chianina cows, and semi-wild horses before descending through the charming village of Collepino, olive groves, and alongside an ancient Roman aqueduct to the walled village of Spello. Following a return transfer to Assisi, you can continue your exploration of the city center, including the magnificent 13th-century Basilica of St. Francis, with its priceless late medieval frescoes by Cimabue and Giotto among others, one of Italy’s great Christian pilgrimage destinations and a UNESCO World Heritage site since 2000. You celebrate your week of discovery with dinner at an outstanding favorite restaurant, where you may have the very Umbrian strangozzi pasta topped with truffle sauce or black-olive pesto, grilled meat or rabbit cacciatore, and a house-made fruit torte to complete the meal.

Overnight in Assisi

After breakfast, you depart at your leisure and on your own for connections home or to your next destination.

You are met at the Orvieto train station and transferred the short distance up to the medieval city situated on a plateau above steep cliffs made of volcanic tufa stone. Orvieto floats almost like an island over the Umbrian countryside of olive groves and vineyards. Compact and easy to navigate, the city’s historical center is a perfect introduction to Umbria—it has been inhabited for millennia, from the Etruscan period through its Roman conquest, and centuries later gained prominence in the Middle Ages. A stroll through the charming pedestrian center begins at its striking 13th-century cathedral with gold facade and striped walls. Orvieto also features fascinating subterranean sites—a network of caves and tunnels used in times of siege or for storing wine, as well as the Pozzo di San Patrizio—St. Patrick’s Well—all built in the 16th century. You can peruse the region’s distinctive painted ceramics in the many shops, perhaps while enjoying a delicious gelato. Later, to accompany dinner, you may enjoy a glass of Orvieto—the dry or semi-sweet white wine that shares the city’s name, produced from grapes grown on surrounding hillsides.

Accommodation: Hotel Duomo, Orvieto

5.2 or 9.8 miles, easy to moderate, 1,300-ft. elevation loss and 500-ft. elevation gain

After breakfast, a 30-minute drive takes you through the rolling Umbrian countryside with views back to Orvieto to the start of the day’s walk in the Area Attrezzata Sette Frati, located in the Monte Peglia Natural Park. The full day’s walk gently descends over a well-signed and maintained gravel track through a tranquil landscape, alternating between typical Mediterranean forest of holm oak and low shrubs such as broom and blackberries, cultivated fields, and open meadows with abandoned farmhouses—a perfect setting for a picnic lunch. You soon understand Umbria’s nickname as the “green heart of Italy” before a final ascent delivers you to your home for the next two nights—a secluded hilltop country farmhouse with panoramic valley views. Dinner tonight is on-site at the farm’s warm, wood-beamed restaurant.

Accommodation: Podere le Corone, Monte Castello di Vibio

6.2 miles, easy to moderate, 500-ft. elevation gain and loss

This morning, you depart the hotel for the day’s destination—the medieval hamlet of Titignano. Today this village is a sprawling estate featuring a 12th-century castle, winery, and farm buildings—all gathered around a central square with sweeping views of Lake Corbara. Created by a hydroelectric dam on the Tiber River, Lake Corbara is a scenic rural reservoir; surrounding it are acclaimed vineyards producing DOC-certified red wine. In this region, much of the landscape is of cultural and natural significance, including the Tiber river basin, nearby lakes, and many towns. Habitats for migratory and resident birds share space with the archaeological remains of Etruscan and Roman civilizations, as well as medieval castles and ruins. Your walk starts on a paved, low-traffic country road and continues onto a mix of gravel roads and grassy trails through the Umbrian countryside. Enjoy views of beautiful fields dotted with villas and deep oak forest, as well as the distant hill town of Todi before reaching the piazza of Titignano. Here, enjoy gorgeous vistas over expansive vineyards and down to Lake Corbara. You are then welcomed to lunch with a glass of the property’s renowned wine—produced in the surrounding hillsides. An afternoon transfer returns you to Podere le Corone where there is time to enjoy the seasonal outdoor pool or simply relax enjoying the views before dinner once again in the hotel’s dining room. For an additional, optional walk before or after dinner, amble to the neighboring town of Doglio, a tiny village with sweeping panoramas of the surrounding valley.

Accommodation: Podere le Corone, Monte Castello di Vibio

6.8 miles, easy to moderate, 200-ft. elevation gain and 750-ft. elevation loss

Today, experience a trio of medieval hilltop towns as you stroll through the pastoral countryside of the Tiber Valley. This morning, you transfer approximately 20 minutes to the tiny fortified village of Monte Castello di Vibio, described by the 16th-century architect and painter Cipriano Picolpass as “an ideal life.” Here, you have time to explore the main piazza, with its panoramic views and baroque church, the crenulated tower of Portia di Maggio, the defensive walls, and the diminutive Teatro dell Concordia—with only 99 seats it is billed as the smallest theater in the world. After strolling the ancient stone streets of this perfectly preserved town—perhaps stopping at a local bar for a coffee or the village grocer to pick up picnic supplies—you set off into the countryside, enjoying sweeping views across the Tiber Valley. Descending through olive groves and vineyards, your route passes by the Rocca di Cecanibbi, a medieval watchtower, before you arrive in the small, fortified hamlet of Cecanibbi, a cluster of stone houses clinging to the walls of a massive medieval castello. The final section of today’s walk is along the Tiber River, used by the Romans to sail wine and olive oil to Rome. At the walk’s end, your driver meets you and brings you to Montefalco, known as “the balcony of Umbria” for its dramatic hilltop perch. With its five gates and five-sided piazza, this medieval town is renowned for its DOCG wine, Sagrantino, traditional linen, and St. Francis Museum, which contains artwork and frescoes depicting the saint, including “Scenes from the Life of Saint Francis” by Florentine Renaissance painter Benozzo Gozzoli. Following an optional visit to the Antonelli San Marco winery for a tasting of their excellent wines, including Sagrantino di Montefalco DOCG, take time to amble through Montefalco’s cobblestone streets before transferring onward to the beautiful walled town of Spoleto, your home for the next two nights. Built at the head of a wide valley, Spoleto spills over a hillside, with its main sights concentrated in the compact upper town. After settling in your hotel, take time to stroll out this evening, perhaps over the 14th-century Ponte delle Torri (Bridge of Towers), for a wonderful overview of the region.

Accommodation: Palazzo Dragoni, Spoleto

8 miles, easy to moderate, 900-ft. elevation gain and 2,200-ft. elevation loss

This morning, a short taxi transfer delivers you up to the neighboring peaceful resort village of Monteluco—home to the Bosco Sacro (Holy Wood) as well as a convent established by St. Francis in the 13th century. Following an exploratory wander, you enter the wooded slopes of Monteluco, held sacred by the Romans and medieval Christians including St. Francis, who was fond of meditating here. A gentle ascent along the Via di Francesco (also known as the Via di Roma)—the road along which St. Francis walked the hundreds of miles to Rome—leads you to the summit and fork of Castelmonte for panoramic views of the mountainous Valnerina river valley. Following a descent through the forest along the medieval aqueduct, take in spectacular views of the Ponte delle Torri before meandering back into town. This afternoon there may be time to visit Spoleto’s many sights and simply absorb its special atmosphere. Its 14th-century defensive castle, the Rocca Albornoziana—now an interesting museum—presiding from the town’s highest point, was built on the site of a Roman acropolis. The delicate pink-stone main cathedral, the Duomo of Spoleto, dating from the 12th century, was built on the site of an early Christian temple and features stunning Renaissance frescoes by Florentine artist Filippo Lippi. You may also choose to visit the Casa Romana museum, believed to have been the house of the Emperor Vespasian’s mother, and the Roman Theater, still used for performances during the Festival of the Two Worlds, held annually over 17 days in late June and early July.

Accommodation: Palazzo Dragoni, Spoleto

7.7 miles, easy to moderate, 1,450-ft. elevation gain and 1,000-ft. elevation loss

This morning, a transfer takes you through the heart of Umbria to the start of the day’s walk at Valfabbrica. Today you follow the historical route known as the Franciscan Trail, the route by which St. Francis was brought back to Assisi when he was found seriously ill by a group of horsemen. The terrain is gently undulating—alternating between oak forest and open pasture, interrupted by old stone farmhouses and parish churches, dovecotes, and crumbling fortress towers on prominences above. The final portion rising to the Basilica of Assisi is steep but short, and while challenging, it is exhilarating to arrive on foot in the city that is a spiritual destination for many and also a UNESCO World Heritage site. You continue on foot to your hotel in the historical center, just around the corner from the Roman Temple of Minerva, now the Renaissance church of Santa Maria sopra Minerva, and the Basilica of St. Clare, built in the 13th century for St. Clare of Assisi, the founder of the Order of Saint Clare.

Accommodation: San Crispino Residenza d’Epoca, Assisi

10 miles, easy to moderate, 500-ft. elevation gain and 3,700-ft. elevation loss OR 5.3 miles, easy to moderate, 1,200-ft. elevation loss

After breakfast, there is a short transfer to the Natural Park of Mount Subasio, a protected area with serene paths meandering through open meadows as well as oak and pine forest. Mount Subasio is the sprawling mountain on whose flank Assisi is built. A haven of subtle beauty and spirituality, it was here that St. Francis prayed and communed with the birds, all gathered on tree branches (there is an option to stop en route to your walk at the Eremo delle Carceri—the famous hermitage of St. Francis). Hiking in the meadows along the summit of the mountain, you are likely to see grazing herds of sheep, white Chianina cows, and semi-wild horses before descending through the charming village of Collepino, olive groves, and alongside an ancient Roman aqueduct to the walled village of Spello. Following a return transfer to Assisi, you can continue your exploration of the city center, including the magnificent 13th-century Basilica of St. Francis, with its priceless late-medieval frescoes by Cimabue and Giotto. The basilica is one of Italy’s great Christian pilgrimage destinations and a UNESCO World Heritage site. You celebrate your week of discovery with dinner at an outstanding favorite restaurant, where you may have the very Umbrian strangozzi pasta topped with truffle sauce or black-olive pesto, grilled meat or rabbit cacciatore, and a house-made fruit torte to complete your meal.

Accommodation: San Crispino Residenza d’Epoca, Assisi

After breakfast, you depart at your leisure and on your own for connections home or to your next destination.