Assisi to Rome: A Trekking Tour of Italy

A 10 day trip to Italy & Vatican City 
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The walking routes to Rome are lined with picturesque olive groves and emerald oak forests, historically guiding pilgrims to the Eternal City. Your custom tailored tour combines the majesty of the countryside with the charms of the secluded hilltop towns around the Italian regions of Umbria and Lazio. Hike the trails that circle hidden crater lakes, discover an enchanting vineyard situated in an antique stone farmhouse and nourish your body and mind with a refreshing dip in the ancient thermal baths. Immerse yourself in the splendors of the landscape and culture as you follow the Via Francigena from Assisi to Rome.  

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General Information

Inside the Colloseum, Rome.
Detailed Itinerary

Places Visited 

Assisi, Spoleto, Gubbio, Orvieto, Pinacale, Montefiascone, Viterbo, Vetralla, Rome, Monte Subasio National Park, Perugia, Lake Bolsena, Spello, Vatican City  

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Assisi – Arrive in Rome and Transfer to Assisi with an Introductory Tour

The Umbrian plains spread across the landscape from the base of Monte Subasio. Woods rise along the slopes to the peak above the marbled city of Assisi, birthplace of St. Francis. Your private transfer will meet you at Fiumicino Airport in Rome and escort you north into the region of Umbria and the entrance of the hillside town. Assisi stands at an elevation of 1,300 feet above sea level and looks out over the meadows in view of the regional capital, and former rival, Perugia. Check-in to comforts of your hotel located in a 13th-century Benedictine nunnery. The original cellars have been refurbished to contain a luxury spa, easily accessed for your relaxation after a full day of trekking through the wonders of the region.

Your guide will meet you in the hotel lobby keen to introduce you to the charms of Assisi, beginning with the picturesque castle of Rocca Maggiore. The old cobblestone road leads to the top of the hillside and the walls of the storybook fortress. Cardinal Albornoz patronized the structure in the 14th-century, and the main wall extends from the castle entrance to the tower to offer pristine panoramas of the landscape. A tunnel connects the tower to the castle, along with a recessed wall once used to protect sentries from imposing armies. Costumed figures inside the castle walls showcase the typical clothing of nobility in the region during the 14th-century.

What’s Included: accommodation, transfer, tour, dinner

Day 2: Assisi – Trek along the Vale of Spoleto to Discover Town of Spello

In the morning the breeze will brush through the meandering olive groves around the city and carries a surprisingly sweet and herbaceous aroma. After breakfast, your guide will lead you into the forested gorge nearly two miles above Assisi to see the hermitage of Eremo delle Carceri. Steps and bows form petals that encircle a smooth pink stone to create a unique grotto. In the 13th-century, St. Francis would retreat to the oratory, and other monks soon followed. An oak tree more than eight centuries old continues to stand near the stone bridge.

Your guide will lead you through the valley along the trail that leads to Spello. Emerald grass blankets the rolling hills and thick oak forest overtakes the meadows. The village of Spello glows with honey-hued houses that overtake the hillside. Three Roman gates continue to guard the city, and the towers resemble chess pieces that protect the labyrinthine streets. Residents hang flower pots from their shuttered windows, and the vivacious petals add layers of riotous color to the streets, along with graceful floral aromas. The Museum of Pinacoteca has its galleries inside the 16th-century Canonici Palace. The museum exhibits artwork crafted between the 13th and 18th-centuries, including textiles and jewelry.

What’s Included: accommodation, tour, breakfast

Day 3: Assisi – Enjoy a Day at Leisure around the Landscape and Town of Gubbio

The morning light will spread across the valley and streaks the emerald plains with flecks of gold. The aroma of espresso spills out of the charming cafes that line the main square of Santa Maria degli Angeli Your guide will meet you after breakfast and lead you first to the Basilica di San Francesco. The structure contains gorgeous embellishments, from the cloistered exterior that leads into town to the graceful rose window that overlooks the upper forecourt. The church was erected in the 13th-century and contains two main levels; the lower church contains the High Altar beneath which St. Francis was buried.

The catacomb atmosphere of the lower church fades with the bright colors of the decorative frescoes along the walls as each depicts St. Francis’s life as it parallels the life of Jesus. After your morning visit to the Basilica, you will venture along the ancient path that meanders through the hills to the city of Gubbio. The medieval atmosphere emanates from the imposing architecture that is perched on the steep slopes of Monte Ingino. Gothic buildings ascend the hillside, along with the open-air cable car known as the Funivia Colle Eletto.

The cable car provides an exhilarating ride to the top of the mountain that turns the mountainous topography of the city into little more than a slight angle when viewed from above. The valley spreads into the distance in an unforgettable panorama. The Basilica di Sant’Ubaldo crowns the summit and contains a glass coffin inside which lies the body the 12th-century St. Ubaldo. You can experience the ancient qualities of the city displayed along Via Federico da Montefeltro as the 13th-century Cathedral shines pink in the passing sunlight. A 12th-century stained glass window adorns the façade and a local art gallery in the piazza can trace the history of the region back more than 2,000 years.

What’s Included: accommodation, tour, breakfast

Day 4: Orvieto - Explore the Perugia and the Town of Panicale en route to Orvieto

The cafes along Piazza del Comune open their doors in the morning near the ancient portico of the Temple of Minerva. The exterior was erected in the 1st-century BC, but the interior was converted into a church during the 16th-century. The architecture of Italy includes layers of history, from Renaissance to Medieval, and even remnants of antiquity. Your guide will escort you from Assisi to the city across the valley, Perugia. The capital of Umbria features winding cobbled lanes with views to the patterned files along the banks of the Tiber River.

Students have sat in the open piazzas and wandered the streets of Perugia since the university opened in the early 14th-century. The original Etruscan walls once wrapped around town and encompass more than 9,000 feet. Pockets of the original stone structure rise along the old border. At the heart of the Piazza IV Novembre stands the 13th-century Fontana Maggiore, an impressive period piece crafted by the Tuscan sculptors Nicola and Giovanni Pisano. The pink and white stone add a triumph of color to the dramatic facades that surround the square.

Bronze statues hold the urn from which the water flows into the waiting pool below. Outside of the city, you will find the town of Pinacale, which retains its original character in both culture and architecture. The streets contain an oval pattern in their design, and the medieval walls lead to the towers of the church of Saint Michele Arcangelo. It is also the settlement Hannibal used to make a stand against Roman legions in the 3rd-century BC.

What’s Included: accommodation, transfer, tour, breakfast

Day 5: Orvieto – Traverse the Ancient Streets of Orvieto and the Etruscan Tombs 

The drama of Orvieto comes to life in the morning light as you are perched atop a plateau that overlooks the tufa cliffs. A spectacular Cathedral rises above Piazza del Duomo with black basalt and yellow limestone material that shines in the sun. The Gothic design accentuates the remarkable sculptures, stained glass windows, and gilded mosaics that decorate the façade. Your guide will lead you on an in-depth tour of Orvieto, beginning with the stunning décor of the church, which was founded in the late 13th-century to honor the Miracle of Bolsena.

The oldest districts of the city stand atop the cliff, while the newer neighborhoods are lower and near to the base of the mountain. The palaces behind the Cathedral exhibit devotional art, including a marble depiction of the Madonna and Child set beneath a bronze canopy. Your exploration of the wandering streets eventually brings you beneath the city to the vast underground network of Etruscan caves to highlight the wells and tunnels crafted by the civilization that predates Rome. The caves maintain a refreshingly cool temperature with a variance of up to 10 degrees Fahrenheit from the streets above.

Press your hand to the wall and feel the cool stone that keeps the heat from sinking into the caves. Remnants of medieval life are present in the caves, and your guide will point out aspects of the old pigeon coups and olive presses. The hike will take you away from Orvieto and through the woodlands, and above the trees rises the crater in which you will find Lake Bolsena. Wild boars graze in the wilderness as the scents of oak and chestnut trees drift across the trails. The turquoise water of the lake replaces the image of the promontory upon which Orvieto stands.

What’s Included: accommodation, tour, breakfast

Day 6: Montefiascone – Follow Via Francigena For Panoramic Views and Villages

You will rise early to follow the trails along the scenic ridge that overlooks Lake Bolsena. Purple and yellow wildflowers grow in the fields, and extinct volcanoes gave way to crater lakes that shimmer in the passing light. The scent of olive emanates from the many groves that grow alongside the forest’s edge. You will begin on the Roman road of Via Cassia to reach the town of Montefiascone, situated atop the highest peak of the Volsini Mountains come to an altitude of nearly 2,100 feet above sea level. The lush trees shine emerald in the morning light against the golden-hued buildings that are topped with pink tiled roofs. The rich minerals of the volcanic soil provide perfect conditions for farming.

Grapevines sweep across the undulating landscape around the crater. Etruscans and Romans both grew grapes in the region, whose former settlements now lay beneath the medieval streets of Montefiascone. The antique church of Sant’Andrea rises above the old walls in the heart of the city with its beautiful archway with six uniquely carved sections. Along the trails, your guide will lead you to a vineyard outside of town located in an old farmhouse. The scent of rich earth and floral vines reaches through the windows of the winery. Learn about the differences in the landscape that makes the wine special before you delight in a tasting of the vineyard’s productions.

What’s Included: accommodation, tour, breakfast

Day 7: Viterbo – Visit the Papal Summer Residence and Thermal Baths of Lazio

You will wake up early and venture to Viterbo, known as the City of Popes. The trail winds along the bright orchards and gives way to the aromas of zesty citrus. Antique farmhouses appear in the countryside beneath the lingering cypress trees. The fresh air and delightful scents of the morning countryside urge you along the trail until you reach Viterbo, the largest town in northern Lazio. The streets maintain a relaxed ambiance while surrounded by medieval architecture. Etruscans originally settled the area, which Romans eventually overtook.

The town attained its nickname for having been a place of refuge for popes as Rome plunged into internal chaos and feuds. The Gothic architecture of the Palazzo dei Papi borders Piazza San Lorenzo and was erected in the 13th-century to house the popes eager to escape Rome’s turmoil. The colonnade offers a view into the Sala del Conclave, the room which housed the first papal conclave, which was also the longest papal conclave to date that lead to the election of Pope Gregory X.

The 15th-century hall of Palazzo dei Priori includes a series of impressive halls decorated with frescoes that depict the city’s ancient origins that frame the Renaissance Piazza del Plebiscito. Outside of town, you can visit the Bagnaccio Terme as the water bubbles up in the heart of the countryside from sulfurous pools acclaimed for their natural healing properties. Steam rises from the water’s surface, and the refreshing waters are the perfect way to relax your muscles after nearly a week of hiking the Italian landscape.

What’s Included: accommodation, tour, breakfast

Day 8: Vetralla – Relish the Landscape of Lazio and Enjoy a Pasta Making Class

The sunlight will wash over the turquoise waters of Lake Bolsena and the slight ridges of the encircling crater. You will leave the town of Montefiascone behind and after breakfast will hike along the forests of Cimini Regional Park. The Bomarzo Monster Park, known for its fantastic sculptures made from volcanic tuff, features pieces that depict monsters and mythologies dating back to the 16th-century. The trees open to sporadic views of Lake Vico and the peaks of the Venere Mountains undulate above the canopy.

The forest gives way to groves of hazelnut and chestnut trees, and the semi-sweet aroma will lead you to the dry stone walls of Vetralla, located on the rocky promontory of Mount Fogliano. Three historic roads converge at Vetralla: Via Cassia, Via Clodio, and Via Aurelia. Etruscan tombs were carved into the cliffs, and rocky niches along the hill as stone passageways meander beneath the medieval streets of the contemporary town. The alleys are narrow with historical homes that were erected in close quarters and open up to hidden piazzas.

In the afternoon, you will meet a local chef that specializes in regional cuisine, including the traditional homemade pastas. Enter the large kitchen to learn the basics of making the fresh pasta, from the creation of a flour crater at the center of which you crack the eggs, to the slow combination of the ingredients until you have made the perfect dough. Spread the dough out into a thin sheet and begin to segment the pasta in squares to make ravioli. One of the inherent flavors of Vetralla is a porcini mushroom, and the chef will help you harness the taste of the mushroom in both a sauce and stuffed inside the homemade ravioli.

What’s Included: accommodation, tour, breakfast, dinner

Day 9: Rome – Travel to Rome for an All Day Urban Hike Tour of the Eternal City

Rome will stir a deep excitement within you.  Antiquity, elegance, and power combine inside the museums and along the streets for a dramatic representation of over two millennia of history. After breakfast, you will travel to Rome by way of Sutri, a town less than 20 miles south of Viterbo. Ravines surround the narrow hill that looks out into Lazio. Rectangular blocks of tuff shape the ancient city walls along the south side of town, and your guide will lead you to the Roman amphitheater, which architects have carved into the hillside to use the land’s natural gradient to shape the stadium seating. The elliptical design overtook more than 160 feet by 130 feet.

The dramatic image of an ancient arena grows as you reach Rome and see the Colosseum as it towers above the former heart of the empire at more than 150 feet tall. Your guide will lead you through the cobblestone streets of the old city turning the monuments of Rome into the ultimate landscape along your urban hike that ends at St. Peter’s Square. Graceful pillars line the street, and the elliptical piazza is focused on the elegant architecture of St. Peter’s Basilica. Michelangelo designed the dome, which reaches a height of nearly 450 feet. You can take the stairs to the top of the cupola for a view of the opulent artwork of the Cathedral, along with the pink rooftops of Rome.

What’s Included: accommodation, transfer, tour, breakfast

Day 10: Rome – Depart for Home

In the morning, the active Romans venture to the Borghese Villa to enjoy the trails of the trails that crisscrossing the lavish gardens. Runners embrace the cobblestone streets along the Tiber River and pass the mixture of ancient and Renaissance history that create the historical city center. The Roman Forum marks the heart of ancient Rome and contains sprawling ruins, from temples to porticos. You could spend another week just walking around Rome to explore the wealth of artifacts, culture, and tradition held within the boundaries of the ancient city walls. Extend your stay in Italy to hike the trails of the Amalfi Coast, or continue even farther south to Sicily. When you are ready, your private transfer will greet you at your hotel lobby and escort you to Fiumicino Airport for your flight home.

What’s Included: breakfast, transfer


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.