Strada della Contessa: slow tour from Gubbio to Urbino

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.

This itinerary leads to Urbino, across a landscape shaped by history, nature, and culinary traditions. Along the way, we’ll travel through quiet valleys, hidden villages, and breathtaking scenery — all at a relaxed pace by bike 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 along the border between Umbria and Marche, eventually reaching the beautiful city of Urbino. 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: Urbino is about 55 kilometers away, while the total route covers 130 kilometers. For this reason, those who are not very fit can rent an e-bike, allowing them to enjoy the charm of the area without strain.

Exploring the Strada della Contessa and Montefeltro 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 through Umbria and Montefeltro 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 can take a short detour: a stretch of the Ancient Via Flaminia leads us to 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 soon arrive in Cantiano, a small village awarded the Touring Club’s Bandiera Arancione, known for its sour cherries and the local Catria beer, brewed with regional barley and spring water from Mount Catria. By late morning, we reach the town of Cagli, about halfway through the day’s route.

Cagli is a town with strong Roman roots, where the splendid Ponte Mallio stands out—a remarkably well-preserved bridge located in the archaeological area just outside the center.

Strolling through the historic streets, we reach the Torrione, the only surviving structure of the ancient fortress designed by Francesco di Giorgio Martini for Federico da Montefeltro. Today, this imposing cylindrical bastion houses the Center for Contemporary Sculpture, featuring works by internationally renowned artists in a unique and harmonious setting.

Let’s take our time to explore the town and recover from the morning ride. When we’re ready, we continue along the ancient path of the northern Via Flaminia until we reach Acqualagna, the truffle capital. From here, we turn onto the SP43, a scenic road that winds through the green, rugged hills of Montefeltro.

Only 16 kilometers remain before we arrive in Urbino, UNESCO World Heritage Site and symbol of the Italian Renaissance. Our second day ends here, with a well-deserved dinner in one of the restaurants in the historic center.

Day 2 highlights:

- Strada della Contessa.

- Roman Bridge on the Ancient Via Flaminia.

- Torrione, Cagli.

- Northern Via Flaminia.

- Hills of Montefeltro.

- Dinner in Urbino.

While yesterday was dedicated to the natural and historical wonders of the region, today we delve into the extraordinary art of Urbino, birthplace of Raphael and a true laboratory of the Renaissance.

For centuries, this hilltop city in the Montefeltro region has embodied the humanist ideal of beauty, harmony, and knowledge. It is no coincidence that the celebrated concept of the “ideal city” originated here, portrayed in the famous painting preserved in the Palazzo Ducale.

Let’s begin our visit with this remarkable architectural complex, the symbol of Urbino and the realized dream of Duke Federico da Montefeltro, who envisioned it not only as a display of power but as a true cultural hub. Strolling through its courtyards and stairways, we reach the Duke’s Studiolo, a small chamber lined with exquisite wooden intarsia that perfectly represents the harmony of the Renaissance.

The palace also houses the National Gallery of the Marche, home to masterpieces by Piero della Francesca, Titian, Paolo Uccello, and, of course, Raphael.

Let’s spend a relaxing afternoon strolling leisurely through the streets of Urbino, wandering along narrow alleys filled with charming glimpses and sweeping views, always accompanied by the unmistakable silhouette of the Palazzo Ducale’s towers.

Our path leads us to the Raphael’s Birthplace, where the young artist took his first steps under the guidance of his father, Giovanni Santi. Inside the small museum, visitors can see some of Raphael’s early frescoes and period furnishings. But more than the artworks, it’s the quiet, intimate atmosphere that reveals the deep bond between the painter and his hometown.

We end the day at the Albornoz Fortress, perched on a hill overlooking the Palazzo Ducale. Originally built in the 14th century, the fortress was later modified by the Montefeltro dynasty to strengthen Urbino’s defenses.

The walk up to the fortress offers beautiful views of the city walls and the surrounding countryside. From the top, we admire the bastions and, above all, one of the most iconic vistas of Urbino — the perfect place to end the day with a stunning overview of the city.

Day 3 highlights:

- Palazzo Ducale of Urbino.

- National Gallery of the Marche.

- Raphael’s Birthplace.

- Albornoz Fortress.

We leave behind the beautiful town of Urbino and begin pedaling once again through the rolling hills of the Montefeltro region. We retrace our steps back to Acqualagna, before taking a short detour to the famous Gola del Furlo, a spectacular canyon carved into the rock.

We can follow the Candigliano River along the trail that leads to the ancient Roman tunnel, a remarkable engineering feat still accessible today. Or — only for the more experienced riders or those with an e-bike! — we can take the narrow, steep Monte Furlo road (paved only at the beginning, then turning into a gravel path), climbing up to the Furlo mountain refuge. From here, a short trail leads to the Terrazza Alta, where we’ll be rewarded with breathtaking views.

After this brief but thrilling dive into nature, we return to Acqualagna. Unlike on the outbound journey, this time we have the chance to stop at the Truffle Museum — the perfect opportunity to learn about its deep cultural significance and to recharge with a guided tasting of local dishes. Obviously, all truffle-based!

Let’s continue along the Via Flaminia heading south to Cagli, then turn off onto the SP29, a peaceful road winding through gentle hills. Along this stretch, we slow our pace and let ourselves be guided by the understated, authentic beauty of Umbria.

Just before reaching Secchiano, a short stop takes us to the trail leading to the Cascata del Mulino (Mill Waterfall): an easy path, just over a kilometer round trip, that offers a truly bucolic setting. The sound of water tumbling over rocks invites us to pause and enjoy a moment of pure relaxation.

From here, another hour and a half of cycling takes us to Pietralunga, a small, picturesque village with a fascinating historic center, dominated by the Rocca Lombarda and the Church of Santa Maria, which dates back to the 7th–8th century.

We can spend the night in the village or nearby, choosing from the many farm stays nestled in the countryside—perfect places to enjoy local products: cured meats, cheeses, or homemade pasta such as delicious tagliolini with truffle, mushrooms or goose ragù.

Day 4 highlights:

- Gola del Furlo.

- Truffle Museum in Acqualagna.

- Cascata del Mulino Trail.

- Village of Pietralunga.

- 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 22 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 and Le Marche, from Gubbio to the Strada della Contessa, Urbino and the Montefeltro area. 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.