Cycling through History & Art – Discovering the Malatesta Lands, Montefeltro and San Marino

Day 1 – Arrival in Rimini

Welcome to Rimini, one of the most famous seaside towns on Italy’s Adriatic coast. After your arrival, take time to discover the historic city center, rich in Roman and Renaissance heritage. Highlights include the impressive Arch of Augustus, the ancient Tiberius Bridge, and the majestic Castel Sismondo, once home to the Malatesta family.
Dinner at leisure and overnight stay in Rimini.

Day 2 – Cycling from Rimini to Santarcangelo di Romagna

(approx. 40 km / +200 m)

Your cycling holiday begins with a scenic ride inland along the Uso River bike path. You will pass through Bellaria, San Mauro Pascoli, and the elegant Villa Torlonia, continuing towards Savignano sul Rubicone, famous for its Roman bridge. The route then climbs gently through rolling hills dotted with vineyards and olive trees before reaching Santarcangelo di Romagna, a charming medieval village full of character.
Dinner on your own and overnight stay.

Day 3 – From Santarcangelo to San Leo Fortress

(approx. 40 km / +500 m)

Today’s ride takes you deeper into the peaceful countryside of the Rimini hinterland, between the Uso and Marecchia valleys. Cycling along quiet hilly roads, you will pass through Pietracuta before reaching the spectacular hilltop town of San Leo. Known for its dramatic fortress and panoramic views, San Leo is one of the jewels of the Montefeltro region.
Dinner at leisure and overnight stay.

Day 4 – Cycling Across Borders to San Marino

(approx. 45 km / +600 m)

This stage is one of the most unique of the tour, as you cross multiple borders between Romagna, Marche, and the independent Republic of San Marino. The route winds through picturesque villages such as Monte Cerignone, Carpegna, Monte Grimano Terme, and Mercatino Conca, before arriving in San Marino, the world’s oldest republic, perched high on Mount Titan.
Dinner on your own and overnight stay.

Day 5 – From San Marino to Pesaro via Medieval Villages

(approx. 60 km / +600 m)

A day filled with postcard-perfect landscapes and historic villages. You will first reach Saludecio, famous for its painted murals, then continue through Mondaino and Montegridolfo, two beautifully preserved medieval towns. The ride then leads to the legendary Castle of Gradara, one of Italy’s most romantic fortresses, before descending towards the Adriatic coast and arriving in Pesaro.
Dinner at leisure and overnight stay.

Day 6 – Scenic Coastal Ride Back to Rimini

(approx. 45 km / +400 m)

Your final cycling stage follows La Panoramica, considered one of the most beautiful cycling roads in Italy. Riding through the stunning Monte San Bartolo Regional Park, you will enjoy unforgettable coastal views between Pesaro and Gabicce Monte, with stops in Fiorenzuola di Focara and Casteldimezzo. The route then returns to Romagna, ending your journey back in Rimini.
Dinner on your own and overnight stay.

Day 7 – Departure

After breakfast, your cycling tour in Emilia-Romagna and San Marino comes to an end. Departure and end of services.