20/03/2025

This adventure is told by Silvia Donatiello, who, together with her friends, had a unique experience cycling through the wonders of the Malatesta Lands and Montefeltro, exploring breathtaking landscapes and uncovering hidden history in every corner.

A Journey through Two Regions: Emilia-Romagna, Marche, and San Marino

There is something magical about cycling through history, immersed in landscapes that seem to come straight out of a painting. Last year, with a group of friends, we decided to explore the Malatesta Lands and Montefeltro by bike, crossing two regions – Emilia-Romagna and Marche – and the Republic of San Marino, in search of medieval villages, castles, and panoramic roads. This journey allowed us to discover a territory where time seems to have stood still, filled with the charm of ancient rivalries and landscapes that unfold at every turn.

The Historical Charm of Rimini and the Romagna Villages

Our journey began in Rimini, a city with two faces: on one side, its coastal charm, and on the other, a historic center rich in wonders. We strolled between the Arch of Augustus and the Tiberius Bridge, reliving the Roman and Renaissance essence of Rimini, before reaching Castel Sismondo, a testament to the power of the Malatesta family. After a delicious dinner with piadina and a glass of Sangiovese, we were ready to begin our adventure.

The Authentic Villages and the Impressive San Leo Fortress

Leaving the coast behind, we headed inland along the Uso River bike trail, passing through small, authentic villages. In Santarcangelo di Romagna, the atmosphere was both intimate and lively: cobbled streets, craft shops, and an underground labyrinth of tuff caves still shrouded in mystery. The ancient village welcomed us with its authentic spirit, offering one of the most beautiful sunsets of the trip. We then cycled towards the imposing San Leo Fortress, following winding roads through the lush valleys of the Valmarecchia. The climb was challenging, but the breathtaking view of the fortress that overlooks the surrounding landscape was well worth the effort. San Leo has hosted popes, emperors, and even the mysterious Cagliostro, who was imprisoned here. Visiting the village felt like traveling back in time, immersed in legends and fascinating stories.

San Marino: The World’s Oldest Republic

Our route then took us to the Republic of San Marino, where we crossed three borders in a single day. The roads wound between Mount Carpegna and Mount Grimano Terme, offering incredible views of the valley. Reaching the world’s oldest republic was a special experience: the view from the three towers that dominate Monte Titano extends all the way to the coast, and as we wandered through the medieval streets, we felt as though we had stepped into another era.

The Beauty of Marche’s Villages and the Story of Gradara

Leaving San Marino behind, we ventured into the Marche region, visiting villages such as Saludecio, Mondaino, and Montegridolfo, where time seems to have stopped. Silent roads, fortified walls, and frescoes depicting ancient stories made this part of the journey a constant discovery. The Gradara Castle welcomed us with its imposing structure, narrating the tragic love story of Paolo and Francesca, immortalized by Dante in the Divine Comedy.

The Adriatic Sea and the Panoramic Road of Monte San Bartolo

The final part of our journey led us to the sea, along the beautiful Monte San Bartolo Panoramic Road. This stretch, connecting Pesaro to Gabicce Monte, is one of the most captivating routes I’ve ever cycled: a road that feels suspended between the sky and the sea, with the blue of the Adriatic as a backdrop and the greenery of the Natural Park surrounding us. The villages of Fiorenzuola di Focara and Casteldimezzo provided the perfect break before returning to Rimini, where our journey ended with a toast and the realization that we had lived an unforgettable experience.

A Unique Journey through History, Nature, and Culture

This bike tour was not just a ride through extraordinary places, but a true journey through the history and culture of a region that never fails to surprise at every turn. An experience to live at least once, to feel the wind of freedom on your skin and discover the most authentic soul of Italy.

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