Begin your trip by traveling south from Ravenna on route 67, past Forlì and along the northern edge of Montefeltro to Portico di Romagna. Dante Alighieri, one of the many famous artists who have waxed poetic about this tiny corner of Italy, met his beloved Beatrice in this town, which has not changed much in the intervening centuries. Home to only 300 residents, it boasts a fascinating foot bridge that has remained intact. Walk along the narrow streets paved in terra cotta, flanked by rough stone houses where geraniums provide generous splashes of bright red, and soon you'll start to forget you're living in the 20th century. You'd do well to spend the night in this delightful town.
Next morning, retrace your tracks a few miles along route 67 to Rocca San Casciano, where you'll take the winding, picturesque road toward San Piero in Bagno. You might want to stop along the way in Galeata, to peek into the 5th-century church of Sant'Ellero. Beyond the Carnaio Pass lies San Piero in Bagno, where you turn north onto route 71, past di Quarto Lake and on into tiny Sarsina. The ancient playwright Plautus was born here, and for centuries it has been rumored that exorcisms are performed regularly in the church of San Vicinio. There's a pretty Romanesque cathedral and a small archeological museum.
Continue on route 71 to Cesena, then south on route 9. You should get to Santarcangelo di Romagna just in time for a late lunch at the Osteria Sangiovesa, an inexpensive and unpretentious spot that was a favorite of Federico Fellini, who immortalized this area in his film Amarcord. Be brave and try some local dishes - they have strange names and may sound unappealing, but if you take the risk you'll understand why the Italians consider the food of Montefeltro to be some of the best their nation produces. After lunch, hop back on route 9 and continue south to route 423. Drive a few miles east, then veer right onto the small provincial road to Montegridolfo, a fairy-tale village-in-a-castle. The entire village has been turned into a 4-star inn, and we highly recommend you spend at least one night there.
If you happen to be here between July 25 and August 3, start your next day with a very brief detour to the charming hamlet of Saleducio. During this period the steep narrow streets are lined with murals painted by artists from all over Europe, as part of the 17th-Century Festival. Even at other times of the year it's worth coming here for the view of brilliant green valleys and deep blue sea, either from the terrace at the bottom of the town or from the 18th-century belltower at the top of the hill.
Morciano di Romagna is five miles north, and here you join up with the larger road that will take you east, past one tiny hill after another with names like Mercatino Conca, Monte Cerignone, and Pietrarubbia. Just after Carpegna (famous for its prosciutto crudo), take the six-mile road for Pennabili, an unforgettable hillside journey through dense oak woods, with snow-capped Mounts Carpegna and Simoncello visible in the distance. Pennabilli is actually an "upside-down hill town," being built in a hollow between two cliffs. On one is a medieval castle and Augustan monastery; the other is home to the church of S. Agostino, where you can admire the 15th-century organ.
Now head for route 258 and drive north one mile (towards Rimini), then take another panoramic side road, park your car and walk through the ancient archway into Petrella Guidi, a minuscule hamlet with a 1000-year-old tower you might call the "Chinese Theatre" of Italy. Set into the pavement in the Campo dei Nomi (Name Square) are colorful tiles dedicated to Federico Fellini, his wife Giulietta Masini and Marcello Mastroianni. It is rumored that many movie stars hang out in this town, but don't tell anyone this well-kept secret!
At this point you can take a detour and head for San Leo, which marks the spot where the beaten track begins. When you see the imposing castle that literally clings to the side of its hill, you'll understand why it has become a mecca for Italian travelers. Our itinerary leads us east on route 258 to Verucchio, the last medieval gem on our little-known necklace. This town's 14th-century castle was once home to the Malatestas, the powerful family who ruled over this part of Italy for many years. They were great patrons of the arts, and it seems their interests have become a local tradition: during the summer and fall you'll find excellent concerts and artistic events scheduled in every one of these enchanting rockbound enclaves.