More than thirty villages, five provinces and one common thread: stone, art and landscapes unfolding from the mountainous interior to the sea. This itinerary does not follow alphabetical order, but the more authentic logic of travel: the road. The result is a continuous journey across ridges, valleys and hills, where every transfer becomes an integral part of the experience, never merely a connection.

Province of Ancona: from the silence of the Apennines to the open air of the Conero
The journey begins in the most secluded hinterland, on the border with Umbria, then gradually descends towards the Misa Valley before ending with an open view of the sea. On the Umbrian-Marche side of the Apennines, Sassoferrato preserves deep layers of history: the Battle of the Nations was fought here in 295 BC, and this was also the site of Sentinum, now an archaeological park. The Albornoz Fortress dominates the medieval village, while the Abbey of Santa Croce is an important example of Romanesque architecture in Le Marche. The landscape is austere, and the Arceviese road cuts through dense, silent woods until it reaches Arcevia, in the heart of the Misa Valley. A network of nine castles preserves an almost intact medieval layout within an agricultural landscape considered among the most harmonious in the region. The walls contain works by Luca Signorelli and Giovanni della Robbia, evidence of an unexpected artistic wealth. The village marks the transition from mountain terrain to cultivated hills. The descent continues through badlands and vineyards to Corinaldo, arranged in concentric rings of brick walls that rank among the best preserved in Le Marche. The Piaggia, with its 109 steps, creates a unique urban stage, while the Torre dello Sperone dominates the skyline. The warm colour of the bricks blends with the green lime trees surrounding the town. Entering the Castelli di Jesi area, the road stretches through orderly vineyards towards Morro d’Alba. Enclosed within pentagonal walls, it preserves La Scarpa, a rare covered walkway along the ramparts. From here the view extends from the Sibillini Mountains to the sea. The village is also the heart of Lacrima wine production. After crossing the Esino Valley, the road climbs through the hills to Offagna. The village gathers around its imposing, isolated fifteenth-century fortress. Neoclassical buildings sit within an orderly countryside of vineyards and farmhouses. The hinterland finally opens to the light of the Conero and the Adriatic.

Province of Pesaro and Urbino: from
Montefeltro to the Adriatic, across ridges
and historic valleys
A broad arc leads inland from the coast to Montefeltro, crosses the Metauro Valley and returns to the sea along the Cesano. It begins at Gradara, where the Malatesta fortress dominates a village enclosed by mighty walls. Dante set the story of Paolo and Francesca here, evoked by the interiors and panoramic walkways. The view reaches the sea, while the defensive structure tells of a past that was both strategic and literary. The road climbs through the Conca Valley to Monte Grimano Terme, built in a spiral on a steep slope. Houses cluster along concentric routes in an almost organic layout. The surrounding landscape alternates woodland and gentle hills, marking the border with Romagna. Crossing the Sasso Simone and Simoncello Park, the route reaches Macerata Feltria. Built over the remains of Roman Pitinum, it preserves visible archaeological traces alongside medieval and Renaissance buildings. The village extends between Castello and Mercatale, clearly revealing its historical layers. The thermal baths reinforce the relationship between landscape and settlement. A few kilometres lead to Frontino. Small, compact and built from local stone, it is immersed in a silent landscape of woods and pastures. The Montefiorentino convent houses works of great artistic value. This is a secluded place where rural life still prevails. Descending into the Metauro Valley, the route reaches Mercatello sul Metauro. Developed around an ancient parish church, it retains a clearly legible medieval layout. Its treasures include a Gothic crucifix by Giovanni da Rimini. Details such as the “doors of the dead” recall traditions and rituals now rarely seen. Following the valley and turning into the hills, the road reaches Montefabbri. The village has remained almost unchanged since the fifteenth century, with a compact, quiet urban fabric. Its parish church contains some of the oldest stucco decoration in Le Marche. The surrounding farmland heightens the feeling that time has stood still. The journey continues towards Pergola. Rich in religious buildings, it is best known for the Gilded Bronzes, an extraordinary Roman sculptural group unique in the world. The Cesano Valley landscape is gentle and productive, with vineyards and cultivated fields. Town life maintains a balance between history and contemporary activity. Following the river, the route arrives at Mondavio. A coherently planned Renaissance village, centred visually and symbolically on the Rocca Roveresca. Its urban layout remains orderly and readable. The atmosphere is that of an ideal city built for military and representational purposes. Finally, the route reaches Mondolfo, where the valley opens towards the sea. Enclosed by a double ring of walls, the village overlooks a broad, luminous landscape. Its views of the Adriatic are among the most evocative in the region.

Province of Macerata: from orderly hills
to the landscapes of the Sibillini Mountains
The route crosses the province before climbing back towards the Apennines. Cingoli, perched on high ground, offers one of the widest panoramas in Le Marche, stretching all the way to the Adriatic. The historic centre alternates stone with warm-toned plaster, Renaissance palaces and churches. A work by Lorenzo Lotto bears witness to a lively artistic history. It is a true visual threshold between coast and hinterland. Crossing the San Vicino area, the route reaches Esanatoglia. Stretching along the Esino River, it has a spindle-shaped urban form and numerous bell towers. Medieval frescoes and fountains reveal a strong relationship with water. The setting is intimate, silent and almost suspended in time. Descending, the route reaches Treia. The village is distinguished by its elegant, theatrical horseshoe-shaped square. Renaissance palaces and archaeological remains tell of a long continuity of settlement. Local traditions such as the Disfida del Bracciale keep its connection with the past alive. A short distance away lies Montecassiano. Arranged in concentric rings, the village retains a compact urban structure. Works preserved by its confraternities testify to a strong religious identity. The walls define an intimate, harmonious space. Descending into the Chienti Valley, the route reaches Montecosaro. The Romanesque Basilica of Santa Maria a Piè di Chienti rises from the landscape. Its position between plain and hillside offers open views of the Sibillini Mountains. Agriculture remains fundamental to the local economy. Just beyond lies Montelupone. Uniform in the warm colour of terracotta, it is surrounded by distinctive crops such as the local artichoke. Walls and gates clearly mark its historic boundaries. The village maintains a strong visual coherence. The route then turns towards San Ginesio. Overlooking the Sibillini Mountains, it offers bright, far-reaching views. Its terracotta architecture and frescoed churches bear witness to a rich artistic past. It is one of the most scenic points on the itinerary. Finally, the road reaches Sarnano. The village rises concentrically, its red roofs climbing towards the summit. At the foot of the Sibillini Mountains, it marks the full entrance into the mountain landscape. It feels lively and deeply connected to its territory.

Province of Ascoli Piceno: from the sea
to the badlands of the Piceno area
An itinerary that climbs inland from the coast through landscapes shaped by nature and agriculture. The historic centre of Grottammare overlooks the coast amid orange groves and glimpses of the sea. The village preserves works of art and traces connected with Pope Sixtus V. Its atmosphere combines elegance with sweeping views. Heading south along the Adriatic to San Benedetto del Tronto, the road soon turns inland and reaches Monteprandone. Its cultural roots lie in its patron saint, James of the Marches, a fifteenth-century friar who embodied the original principles of the Franciscan order. From here the road climbs to Ripatransone. Spread across five hills and enclosed by more than two kilometres of walls, Ripatransone was known in the Middle Ages as Propugnaculum Piceni. In 1205 it also became the first rural municipality in Italy to adopt its own statutes. A kilometre-long main street crosses the town, whose treasures include a fourteenth-century palace converted into a theatre. Descending, the route reaches Montefiore dell’Aso. Set between two valleys, it combines agriculture with artistic heritage. Its historic centre preserves fine buildings and works, including a polyptych by Carlo Crivelli. The whole is balanced and beautifully maintained. Finally, the route reaches Offida. Enclosed by walls, it is renowned for bobbin-lace making. The church of Santa Maria della Rocca is one of the architectural masterpieces of Le Marche. The village combines tradition with urban quality.

Province of Fermo: between the Aso and Tenna valleys, the final stretch of the journey
Perched on a rocky spur, Torre di Palme overlooks the Adriatic with broad, luminous views. Flower-lined lanes and a medieval layout create a compact scene enriched by works of art. Climbing inland, the road reaches Moresco. Elliptical in shape, the village is dominated by a distinctive seven-sided tower. The surrounding landscape is orderly and agricultural, conveying balance and restraint. Nearby lies Petritoli.

The neo-Gothic Tre Archi mark the entrance to a town rich in terracotta architecture. Clearly visible medieval traces remain, while its hilltop position affords sweeping views. Finally, the route arrives at Servigliano. Rebuilt in the eighteenth century, it is distinguished by a perfectly geometric plan. Its streets intersect according to a rational scheme. It is a surprising conclusion: from medieval organic form to Enlightenment order.