Strada della Contessa: slow tour around Gubbio

Can 5 days be enough to slow down, shift gears, and see with new eyes a land that holds centuries of history and unspoiled landscapes? Yes, by starting in Gubbio and following the ancient route of the Strada della Contessa, a medieval link between Umbria and Montefeltro.

Following a route that winds along the border with the Marche region, we’ll cross quiet valleys, secluded villages, and enchanting landscapes, enjoying the journey by bicycle or e-bike.

It’s a journey that invites you to experience the region with the right rhythm: taking time to pause, savor each stage, and let yourself be moved by the authentic beauty of a land that speaks to the heart.

Perched on the slopes of Mount Ingino, Gubbio is one of the best-preserved medieval towns in Italy and the perfect starting point for those who want to explore the most authentic side of Umbria, where culture, nature, and food traditions intertwine.

An ancient city by origin, it flourished in the medieval and Renaissance periods as a hub of power and culture. This is still evident today as you stroll through the evocative streets and squares of its historic center, dominated by the imposing Palazzo dei Consoli.

From Gubbio also begins the Strada della Contessa, an old route once linking to the Duchy of Urbino, now a scenic path that connects Umbria and the Marche, crossing the Apennines along quiet, panoramic trails.

The route itself is about 12 kilometers long, but beyond it, we can explore by bike or on foot the white roads and numerous trails that cross the landscapes of Umbria outdoor. An itinerary not to be missed, to fully experience the green heart of Italy’s most hidden treasures.

This itinerary is designed for those who love to travel without haste. In 5 slow days, we’ll learn about the extraordinary culture of Gubbio, before immersing ourselves in the nature surrounding the historic Strada della Contessa, getting in touch with the most authentic soul of the area.

It’s a route that can also be done by car, stopping along the way at the most panoramic points. However, if we truly want to admire the enchanting scenery of the Apennines from a privileged perspective, the best choice is to travel by bike.

Gubbio is the starting and ending point of a 60-kilometer circular route. Those who aren’t trained can rent an e-bike to enjoy the charm of the area without too much effort.

Exploring the Strada della Contessa by bike, we can discover their most authentic side, stopping at farms and agritourisms to taste local products, meet small local producers, or simply take the time to admire the wonders of nature.

Each stop will become an opportunity to build a direct connection with these wonderful places and the locals, turning our journey into an unforgettable personal experience.

Our 5-day slow itinerary in Umbria begins with a day in the enchanting Gubbio, a place rich in historic buildings, cultural landmarks, and archaeological treasures that are simply unmissable.

We start in the lower part of the city, where Gubbio reveals its most ancient roots. Just outside the walls, nestled among meadows and monumental ruins, lies the Archaeological Park of the Roman Theatre. It’s the perfect spot to begin the day: peaceful and quiet in the morning, ideal for sitting among the remarkably preserved stone tiers and soaking in the atmosphere.

Let’s savour the ancient spirit of Gubbio, with views stretching out at the foot of Mount Ingino. From here, we slowly ascend towards the heart of the historic center, passing the gardens of Piazza dei Quaranta Martiri and arriving at the imposing Piazza Grande, the symbolic heart of the town, perched like a terrace overlooking Northern Umbria.

Here, we find the majestic Palazzo dei Consoli with its soaring tower. We spend the rest of the morning exploring its interior, home to the Civic Museum, which houses the Tavole Eugubine — mysterious bronze inscriptions in the Umbrian language, a rare and fascinating relic that has survived the centuries.

Let’s move just a few hundred meters uphill along the narrow and picturesque Via Ducale to reach the entrance of Palazzo Ducale, an elegant example of Renaissance architecture commissioned by Federico da Montefeltro and built at the end of the 15th century.

Inside, the furniture, paintings, and the reconstruction of the duke’s wooden studiolo highlight the palace’s refinement—a truly special place to spend a peaceful couple of hours. We conclude our day with one last unmissable stop: the Basilica of Sant’Ubaldo, located on Monte Ingino and accessible by the Colle Eletto funicular. From there, we’ll enjoy a spectacular view of the city and the valley below.

Let’s return to the historic center on foot along the winding Via Sant’Ubaldo, passing through woods and panoramic views, and spend the evening in one of the local trattorias, savoring typical dishes such as strongozzi with truffles or crescia al panaro accompanied by local cured meats.

Day 1 highlights:

- Archaeological Park of the Roman Theatre.

- Piazza Grande and Palazzo dei Consoli.

- Palazzo Ducale.

- Basilica of Sant’Ubaldo.

- Traditional dinner.

Just outside the historic center of Gubbio, there are several places where we can rent a bike or e-bike to start our outdoor journey toward Urbino (55 km), following a scenic route through the former borders of the Duchy of Urbino.

We take the Strada della Contessa, corresponding to SS452, and follow the signs for Cagli and Urbino. After a few kilometers, we leave Umbria and enter the Marche region, just before reaching Pontericcioli.

Here we turn right, towards Scheggia, and take the road of the ancient Via Flaminia to reach a charming Roman bridge surrounded by nature. The slow pace and peaceful landscape make this segment truly refreshing—ideal for those who enjoy gravel roads and scenic detours guided by the charm of the countryside.

Back on the main road, we continue until we reach the distinctive silhouette of the Ponte a Botte, a cylindrical structure 22 meters in diameter built over the La Foce stream. Its name, "Botte d’Italia," refers precisely to its unique shape, making it one of the most curious and photogenic landmarks in the area.

Just a couple of kilometers remain before the village of Scheggia. Once there, we head inland, leaving the village behind for the moment. Instead, we follow the SS360 winding through the hills, and after about 14 kilometers, we arrive at the Abbey of Sant’Emiliano in Congiuntoli.

The abbey, founded in the 12th century, was once the spiritual heart for Benedictine and Camaldolese monks. Its interior is austere and solemn, telling evocative stories of contemplation amidst pristine nature.

After a reflective pause, we get back on our bikes and return toward Scheggia, crossing an intimate and little-traveled hilly landscape, immersed in wild and captivating greenery. The return is slow and silent, almost natural: we are welcomed by a secluded village, where we’ll spend the night wrapped in the silence and the peaceful breath of the Umbrian countryside.

Day 2 highlights:

- Strada della Contessa.

- Roman bridge on the Ancient Via Flaminia.

- Ponte a Botte.

- Abbey of Sant’Emiliano in Congiuntoli.

We leave behind the quiet charm of the village of Scheggia and head south toward Fossato di Vico, about 16 kilometers away. But instead of following the main road, we turn left just outside the village and take the road that climbs to the Monte Calvario Sanctuary.

Before long, we find ourselves cycling along a scenic gravel road, fully immersed in nature, first through lush woodlands, then along a mountain ridge with open pastures and breathtaking views.

We’ve entered the heart of Monte Cucco Park, a dramatic and unspoiled landscape that invites us to slow down, listen to the wind, and breathe in the pure mountain air.

Here we can leave our bikes behind and take a short hike to the entrance of the Monte Cucco Caves—an extraordinary karst system that plunges over 900 meters underground, with winding canyons and chambers sculpted by water over centuries. One of the best experiences in Umbria, a fascinating journey into a mysterious and otherworldly realm.

Let’s ride along the trails skirting Monte Cucco, through shady beech forests and open stretches with sweeping views across the Umbrian-Marchean Apennines.

Back on the main road, we reach the village of Sigillo, turn left just past the Town Hall, and continue on the road that climbs once again toward Monte Cucco for 12 kilometers, nearly to the summit. Here lies Pian di Monte, a scenic spot with breathtaking views, also known as one of the best paragliding launch sites in the region.

A trail from Pian di Monte leads first to Rifugio Valcella and then continues to the mountain's summit (over 1,500 meters) and the Croce del Monte Cucco. It’s a spectacular but demanding hike, requiring about 4 hours of walking, and is recommended only for well-trained hikers—preferably those who can begin the route earlier in the day.

Then, let's retrace our route: it's only a few kilometers from Sigillo to Fossato di Vico. We arrive by late afternoon and enjoy an evening meal of local flavors: an ideal way to end this day outdoors, celebrating the simplicity and richness of Umbrian cuisine.

Day 3 highlights:

– Monte Cucco Park.

– Monte Cucco Caves.

– Pian di Monte.


– Dinner in Fossato di Vico.

After a day immersed in the nature of Monte Cucco, we slow down and take a quiet morning to explore the village of Fossato di Vico. Its historic center sits high on a rocky spur overlooking the valley below, offering a glimpse into a past that still shapes the town today.

Wandering through its narrow alleyways, stone arches and tightly clustered houses, we discover the village’s medieval soul. The famous rughe—covered passageways built in the 13th century for defensive purposes—once connected the different parts of the town, and still tell stories of everyday life inside the fortified walls.

The Clock Tower and the old Town Hall recall Fossato’s administrative role in medieval times. Among the small churches, San Pietro stands out for its restrained Gothic elegance, while San Benedetto still preserves fragments of ancient, evocative frescoes. Here, beauty and simplicity go hand in hand, capturing the essence of this beautiful, timeless place.

In the afternoon, we get back on our bikes and continue our journey: just over a dozen kilometers separate us from Torre Calzolari.

The ride is peaceful and easy, unfolding along quiet country roads that wind through the Umbrian hills. One of the highlights is the Strada della Cascata, a scenic route offering gentle curves and pastoral views, perfect for a slow pace that allows us to fully enjoy the landscape.

Torre Calzolari is a charming, timeworn village with a stillness that feels suspended in time. There’s even a lovely little chapel worth a short stop. In the surrounding countryside, you’ll find several farm stays nestled in nature, where the only sounds are birdsong and the aromas wafting from the kitchen.

This is the perfect place to try one of the region’s most prized ingredients: truffle. A plate of homemade tagliolini with truffle is the ideal way to end the day, savoring the seasonal, earthy flavors that reflect the depth of Umbria’s culinary tradition.

Day 4 highlights:

- Fossato di Vico, medieval village.

- Torre Calzolari.

- Night at a farm stay.

We begin the last of our 5 slow days at a slightly different pace. In this beautiful area, dotted with farm stays and small rural enterprises, it’s not uncommon to come across places that offer outdoor activities. Among them, horseback riding stands out as one of the most authentic experiences.

So, we leave the bicycle behind for a while and climb into the saddle for a ride along shaded trails and panoramic ridgelines, exploring a landscape that seems untouched by time. The rustling of leaves and the rhythm of the horse help us reconnect—with nature, with silence, and perhaps even with ourselves.

After this immersive and unmissable experience, we get back on our bikes for the final 11 kilometers of our route, bringing our journey to a close in the stunning town of Gubbio.

Our final afternoon is dedicated to discovering the most ancient heart of Gubbio.

Strolling through the medieval districts of San Martino, San Pietro, Sant’Andrea, and San Giuliano, we retrace the city’s old divisions—boundaries that still shape the identity and rhythm of the community, especially during the “Torneo dei Quartieri,” a traditional and captivating archery competition held each summer.

These same districts also come together for the Festa dei Ceri, Gubbio’s most heartfelt celebration. Every May, the town’s streets fill with devotion, vibrant colors, and powerful communal spirit.

Let’s take our time, walking slowly to savor the city’s unique atmosphere. Let’s stop in the artisan workshops of the historic center, where wood and ceramics are still crafted according to techniques handed down through generations.

And let’s not forget to enjoy one last taste of Gubbio’s culinary identity: freshly baked crescia, cured meats from the Umbrian countryside, aged cheeses, and perhaps a glass of local red wine—to end our five-day slow journey in the best possible way, with history, traditions, food, and nature. 

Day 5 highlights:

- Horseback excursion.

- Walk through the medieval districts of Gubbio.

- Break at artisan shops, bakeries, and local venues in the historic center.

We’ve reached the end of this outdoor journey through Umbria, from Gubbio to the Strada della Contessa and Monte Cucco. We travelled along backroads, through quiet villages, and along trails winding through woods and hills, in search of an authentic Italy, made of living traditions, local flavours, and genuine encounters.

This is a route that embraces slowness as a way to connect with the land, far from the crowded paths of mass tourism. Cycling, walking, pausing — every gesture becomes part of a sustainable, mindful experience that respects both places and people.

It’s a way to rediscover the value of time and the charm of a lesser-known Italy, which perhaps is even more beautiful and ready to be experienced for that very reason.