Italy: Umbria & Assisi

You are met at the Orvieto train station and transferred the short distance up to Orvieto, a medieval city on a plateau above steep cliffs made of volcanic tufa stone. The city 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. Orvieto 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 a striking 13th-century cathedral with a gold façade and striped walls. Orvieto also features fascinating 16th-century subterranean sites, including a network of caves and tunnels used in times of siege or for storing wine, and the Pozzo di San Patrizio (St. Patrick’s Well). You can peruse the region’s distinctive painted ceramics in the many shops, perhaps while enjoying a delicious gelato. At dinner, you may raise a glass of Orvieto, which is the dry or semi-sweet white wine that shares the city’s name. The wine is produced from grapes grown on the surrounding hillsides.

Accommodation: Hotel Duomo, Orvieto
Included Meals: Dinner

7.6 miles, easy to moderate, 600-ft. elevation gain and 1,600-ft. elevation loss

After breakfast, you travel 40 minutes through gorgeous rolling Umbrian countryside. Upon arriving in the main piazza of the picturesque medieval village of Civitella del Lago, you may warm up with a stroll among the narrow warrens and inviting squares, passing charming churches and markets. Feel free to stop at one of the mercatos (or perhaps a tiny wine bar we know!) for sandwiches and other picnic supplies to enjoy later on the trail. Your loop walk delivers you to Piazza Belvedere, where you can admire stunning vistas of Lake Corbara, enjoying the village’s perch high above the water.

You bid farewell to Civitella del Lago as you walk through its medieval gate and make your way to the region’s recently developed walking path, Il Cammino dei Borghi Silenti—the Way of the Silent Villages. The idyllic path is about 53 miles in all, traversing the northern slopes of the scenic Amerini Mountains. You walk just a portion of it today through an oasis of unspoiled wilderness and fully intact medieval villages. Well-maintained trails of dirt, gravel, and single-track lead you mostly downhill through forests of oak, hornbeam, and chestnut trees. You pass some of the region’s many fertile fields of wheat, lush olive groves that have grown here for generations, and sprawling vineyards that produce delicious wines. Open meadows overseen by farmhouses lead you to the tiny hamlets of Cerreto and Case Vecchie, delightful with their own poetic beauty and flower-filled balconies hugging stone houses. Then, more vineyards … and the Barberani Wine Company. This bio-organic winery is situated right on the trail, so you won’t be able to resist a stop here for a complimentary tasting of its grechetto and calcaia wines, taking in lovely views of Lake Corbara.

After, you continue down country roads amidst dense woodland, radiant sunflower fields, and more of the area’s ubiquitous olive groves and vineyards. Conclude your unforgettable sojourn with a short ascent to the village of Baschi, a breathtaking compact cluster of stone buildings overlooking the Tiber Valley. Take time here to visit the 16th-century church of San Nicolo and wander its narrow streets, known as i buchi, or “the holes,” so named because their tiny size and diminutive houses and doorways evoke a feeling of stepping into a miniscule passageway. Life is simple and modest here, following a pace not much different from the relaxed rhythms of the trail.

You meet your driver as you wish for a 30-minute journey to your hotel.

Accommodation: Agriturismo Cerqueti, Morre
Included Meals: Breakfast, Dinner

7.5 miles, moderate, 1,050-ft. elevation gain and 1,100-ft. elevation loss

Begin once again with a ride to Civitella del Lago. Today, however, you head east out of this hilltop village. Follow the CAI Travel 716—part of the Italian Alpine Club system—along a paved country road. Then a gravel track extends four miles, climbing and descending through a scenic patchwork of shimmering olive groves, prolific farmland, and large swathes of shady oak, chestnut, and hornbeam forest. Arrive in the quaint village of Morruzze, where you may pause to explore its 12th-century medieval castle and take in more fantastic views. Stone houses, charming piazzas, and a few dozen friendly local Morruzzesi residents lend this hamlet its unique character.

Here, you pick up Il Cammino dei Borghi Silenti again. As you continue, you’re just a few hundred yards from the Scoppieto Archaeological Area, where excavations have revealed evidence and relics from some of the region’s early settlements. Chalices, cups, plates, and other crockery were forged here in the late first century BC. The clay soils and trees here were key to the factory’s function. Your trail also passes the curious Buche del Vento, or wind holes. The cracks that you see in these rocks lead down to vast underground caverns. Through these crevices, air is constantly exchanged between two worlds—ours and the subterranean. Depending on pressure conditions, a strong jet of cold air might blow from below or bursts of warm air might get sucked in. It’s a fascinating phenomenon to witness!

From here, you follow a trail along scenic country lanes and field tracks to some of Umbria’s most secluded and charming villages. In the pretty stone hamlet of Morre, you might take time to grab a snack in the grocery or a refreshing beverage at a bar. Continue your route through this breathtaking countryside, surrounded by rolling hills and peaks and peering onto farmlands and homesteads where life is lived much as it has been for centuries. Take your time … soak it in. You will find your stroll to be equal parts soothing and invigorating.

After settling into your farmhouse hotel, enjoy a dinner of freshly sourced ingredients and local Umbrian delights.

Accommodation: Agriturismo Cerqueti, Morre
Included Meals: Breakfast, Dinner

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

Today, you’ll experience a trio of medieval hilltop towns as you stroll through the pastoral countryside of the Tiber Valley. You’ll be driven 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. There will also be time to see 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.

Stroll the ancient stone streets of this perfectly preserved town, and perhaps stop at a local bar for a coffee or at the village grocer for trail snacks. Then, 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, which features 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 walk’s end, you arrive in Montemolino, where the Terramante Winery welcomes you. Nestled along the Tiber River, this family winery is passionate about organic, small batch wines from Sangiovese, Sagrantino, and Syrah grapes. In this splendidly scenic place, you savor a lunch of local specialties plucked from the farms of Umbria and sample their unique creations (pending availability; alternative options include a delicious meal in a local restaurant or lovely picnic lunch).

Next, travel about 40 minutes to Montemolino, known as “the balcony of Umbria” for its dramatic hilltop perch. This medieval town boasts five gates and a five-sided piazza, and is renowned for its DOCG wine, Sagrantino. The town is also known for its traditional linen and the St. Francis Museum, which contains artwork and frescoes depicting the saint, such as “Scenes from the Life of Saint Francis” by Florentine Renaissance painter Benozzo Gozzoli. There’ll be time to amble through Montefalco’s cobblestone streets.

Then you move 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, its main sights concentrated in the compact upper town.

After settling in your hotel, you may choose to take a stroll, perhaps over the 14th-century Ponte delle Torri (Bridge of Towers), for a wonderful panorama of the region.

Accommodation: Palazzo Dragoni, Spoleto
Included Meals: Breakfast, Lunch (and Wine Tasting)

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

Satisfied from a delicious breakfast, a short taxi transfer takes you up to the neighboring 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. St. Francis was fond of meditating here.

A gentle ascent along the Via di Francesco (also known as the Via di Roma leads you to the summit and fork of Castelmonte for panoramic views of the mountainous Valnerina river valley. This is the road along which St. Francis walked the hundreds of miles to Rome. Following a descent through the forest along a medieval aqueduct, there will be spectacular views of the Ponte delle Torri before meandering back into town.

This afternoon there may be time to visit Spoleto’s many sights or simply absorb its special atmosphere. Its 14th-century defensive castle, the Rocca Albornoziana—now an interesting museum—presides from the town’s highest point and was built on the site of a Roman acropolis. The town’s main cathedral, the delicate pink-stone Duomo of Spoleto, dates from the 12th century. The cathedral is 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, or visit the Roman Theater, still used for performances during the Festival of the Two Worlds, which is held annually over 17 days in late June and early July.

Accommodation: Palazzo Dragoni, Spoleto
Included Meals: Breakfast

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

In the morning, you’ll transfer through the heart of Umbria to the start of the day’s walk at Valfabbrica. You follow the historical path 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. While challenging, it is exhilarating to arrive on foot in the city that is a spiritual destination for many, as well as a UNESCO World Heritage site.

You continue on foot to your hotel in the historical center. The hotel is 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, which was 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
Included Meals: Breakfast

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 and forests of oak and pine. 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. Your descent takes you 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, featuring 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 an authentic Umbrian meal of 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
Included Meals: Breakfast, Dinner

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

Included Meals: Breakfast

You are met at the Orvieto train station and driven the short distance up to Orvieto, a medieval city on a plateau above steep cliffs made of volcanic tufa stone. The city 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. Orvieto 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 a striking 13th-century cathedral with a gold façade and striped walls. Orvieto also features fascinating 16th-century subterranean sites, including a network of caves and tunnels used in times of siege or for storing wine, and the Pozzo di San Patrizio (St. Patrick’s Well). You can peruse the region’s distinctive painted ceramics in the many shops, perhaps while enjoying a delicious gelato. At dinner, you may raise a glass of Orvieto, which is the dry or semi-sweet white wine that shares the city’s name. The wine is produced from grapes grown on the surrounding hillsides.

Accommodation: Hotel Duomo, Orvieto
Included Meals: Dinner

7.6 miles, easy to moderate, 600-ft. elevation gain and 1,600-ft elevation loss

After breakfast, you travel 40 minutes through gorgeous rolling Umbrian countryside. Upon arriving in the main piazza of the picturesque medieval village of Civitella del Lago, you may warm up with a stroll among the narrow warrens and inviting squares, passing charming churches and markets. Feel free to stop at one of the mercatos (or perhaps a tiny wine bar we know!) for sandwiches and other picnic supplies to enjoy later on the trail. Your loop walk delivers you to Piazza Belvedere, where you can admire stunning vistas of Lake Corbara, enjoying the village’s perch high above the water.

You bid farewell to Civitella del Lago as you walk through its medieval gate and make your way to the region’s recently developed walking path, Il Cammino dei Borghi Silenti – the Way of the Silent Villages. The idyllic path is about 53 miles in all, traversing the northern slopes of the scenic Amerini Mountains. You walk just a portion of it today through an oasis of unspoiled wilderness and fully intact medieval villages. Well-maintained trails of dirt, gravel, and single-track lead you mostly downhill through forests of oak, hornbeam and chestnut trees. You pass some of the region’s many fertile fields of wheat, lush olive groves that have grown here for generations, and sprawling vineyards that produce delicious wines. Open meadows overseen by farmhouses lead you to the tiny hamlets of Cerreto and Case Vecchie, delightful with their own poetic beauty and flower-filled balconies hugging stone houses. Then, more vineyards … and the Barberani Wine Company. This bio-organic winery is situated right on the trail, so you won’t be able to resist a stop here for a complimentary tasting of its grechetto and calcaia wines, taking in lovely views of Lake Corbara.

After, you continue down country roads amidst dense woodland, radiant sunflower fields, and more of the area’s ubiquitous olive groves and vineyards. Conclude your unforgettable sojourn with a short ascent to the village of Basci, a breathtaking compact cluster of stone buildings overlooking the Tiber Valley. Take time here to visit the 16th-century church of San Nicolo and wander its narrow streets, known as i buchi, or “the holes,” so named because their tiny size and diminutive houses and doorways evoke a feeling of stepping into a miniscule passageway. Life is simple and modest here, following a pace not much different from the relaxed rhythms of the trail.

You meet your driver as you wish for a 30-minute journey to your hotel.

Accommodation: Agriturismo Cerqueti, Morre
Included Meals: Breakfast, Dinner

7.5 miles, moderate, 1,050-ft. elevation gain and 1,100-ft elevation loss

Begin once again with a ride to Civitella del Lago. Today, however, you head east out of this hilltop village. Follow the CAI Travel 716—part of the Italian Alpine Club system—along a paved country road. Then a gravel track extends four miles, climbing and descending through a scenic patchwork of shimmering olive groves, prolific farmland, and large swathes of shady oak, chestnut, and hornbeam forest. Arrive in the quaint village of Morruzze, where you may pause to explore its 12th-century medieval castle and take in more fantastic views. Stone houses, charming piazzas, and a few dozen friendly local Morruzzesi residents lend this hamlet its unique character.

Here, you pick up Il Cammino dei Borghi Silenti again. As you continue, you’re just a few hundred yards from the Scoppieto Archaeological Area, where excavations have revealed evidence and relics from some of the region’s early settlements. Chalices, cups, plates, and other crockery were forged here in the late first century BC. The clay soils and trees here were key to the factory’s function. Your trail also passes the curious Buche del Vento, or wind holes. The cracks that you see in these rocks lead down to vast underground caverns. Through these crevices, air is constantly exchanged between two worlds—ours and the subterranean. Depending on pressure conditions, a strong jet of cold air might blow from below or bursts of warm air might get sucked in. It’s a fascinating phenomenon to witness!

From here, you follow a trail along scenic country lanes and field tracks to some of Umbria’s most secluded and charming villages. In the pretty stone hamlet of Morre, you might take time to grab a snack in the grocery or a refreshing beverage at a bar. Continue your route through this breathtaking countryside, surrounded by rolling hills and peaks and peering onto farmlands and homesteads where life is lived much as it has been for centuries. Take your time … soak it in. You will find your stroll to be equal parts soothing and invigorating.

After settling into your farmhouse hotel, enjoy a dinner of freshly sourced ingredients and local Umbrian delights.

Accommodation: Agriturismo Cerqueti, Morre
Included Meals: Breakfast, Dinner

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

Today, you’ll experience a trio of medieval hilltop towns as you stroll through the pastoral countryside of the Tiber Valley. You’ll be driven 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. There will also be time to see 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.

Stroll the ancient stone streets of this perfectly preserved town, and perhaps stop at a local bar for a coffee or at the village grocer for trail snacks. Then, 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, which features 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 walk’s end, you arrive in Montemolino, where the Terramante Winery welcomes you. Nestled along the Tiber River, this family winery is passionate about organic, small batch wines from Sangiovese, Sagrantino, and Syrah grapes. In this splendidly scenic place, you savor a lunch of local specialties plucked from the farms of Umbria and sample their unique creations (pending availability; alternative options include a delicious meal in a local restaurant or lovely picnic lunch).

Next, travel about 40 minutes to Montemolino, known as “the balcony of Umbria” for its dramatic hilltop perch. This medieval town boasts five gates and a five-sided piazza, and is renowned for its DOCG wine, Sagrantino. The town is also known for its traditional linen and the St. Francis Museum, which contains artwork and frescoes depicting the saint, such as “Scenes from the Life of Saint Francis” by Florentine Renaissance painter Benozzo Gozzoli. There’ll be time to amble through Montefalco’s cobblestone streets.

Then you move 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, its main sights concentrated in the compact upper town.

After settling in your hotel, you may choose to take a stroll, perhaps over the 14th-century Ponte delle Torri (Bridge of Towers), for a wonderful panorama of the region.

Accommodation: Palazzo Dragoni, Spoleto
Included Meals: Breakfast, Lunch, (and Wine Tasting)

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

Satisfied from a delicious breakfast, a short taxi ride takes you up to the neighboring 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. St. Francis was fond of meditating here.

A gentle ascent along the Via di Francesco (also known as the Via di Roma leads you to the summit and fork of Castelmonte for panoramic views of the mountainous Valnerina river valley. This is the road along which St. Francis walked the hundreds of miles to Rome. Following a descent through the forest along a medieval aqueduct, there will be spectacular views of the Ponte delle Torri before meandering back into town.

This afternoon there may be time to visit Spoleto’s many sights or simply absorb its special atmosphere. Its 14th-century defensive castle, the Rocca Albornoziana—now an interesting museum—presides from the town’s highest point and was built on the site of a Roman acropolis. The town’s main cathedral, the delicate pink-stone Duomo of Spoleto, dates from the 12th century. The cathedral is 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, or visit the Roman Theater, still used for performances during the Festival of the Two Worlds, which is held annually over 17 days in late June and early July.

Accommodation: Palazzo Dragoni, Spoleto

Included Meals: Breakfast

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

In the morning, you’ll be driven through the heart of Umbria to the start of the day’s walk at Valfabbrica. You follow the historical path 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. While challenging, it is exhilarating to arrive on foot in the city that is a spiritual destination for many, as well as a UNESCO World Heritage site.

You continue on foot to your hotel in the historical center. The hotel is 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, which was 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
Included Meals: Breakfast

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, a short drive brings you to the Natural Park of Mount Subasio, a protected area with serene paths meandering through open meadows and forests of oak and pine. 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. Your descent takes you through the charming village of Collepino, olive groves, and alongside an ancient Roman aqueduct to the walled village of Spello.

Following a return drive to Assisi, you can continue your exploration of the city center, including the magnificent 13th-century Basilica of St. Francis, featuring 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 an authentic Umbrian meal of 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
Included Meals: Breakfast, Dinner

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

Included Meals: Breakfast