San Leo, the rock that named the Montefeltro and imprisoned Cagliostro

San Leo is the day trip from San Marino I’d never skip, and not only for the photo. It’s a whole village perched on a sheer-sided crag, with a single road in cut into the rock and a fortress on its tip that was both a Renaissance military masterpiece and a papal prison. It also has a link with San Marino that hardly anyone mentions.

Leo and Marinus, two stonemasons from Dalmatia

According to the tradition on the municipality’s tourism website, in the late 3rd century two Christian stonemasons arrived from Dalmatia fleeing Diocletian’s persecution. One, Marinus, settled on Mount Titano and founded the community that would become San Marino. The other, Leo, withdrew as a hermit to this rock, then called Mons Feretrius after a Roman temple to Jupiter Feretrius. That name gave us Montefeltro, the historic region, and the saint gave the village its modern name.

To me that shared story is the best reason to do both in the same trip. While San Marino turned its mountain into a republic, San Leo became the fortress everyone wanted.

A fortress that was a capital and a jail

The Romans already fortified the summit, and in the Middle Ages the rock was fought over by Byzantines, Goths, Franks and Lombards. Between 961 and 963 King Berengar II held out here against Otto I’s siege, and the fortress briefly served as the capital of Italy. In 1441 the young Federico da Montefeltro took it with a daring climb, and since the old castle couldn’t cope with artillery he had the Sienese engineer Francesco di Giorgio Martini rebuild it. The result, according to Pietro Bembo, was a «mighty bulwark and marvellous engine of war».

Then came Cesare Borgia, who seized it in 1502, the Florentines and the Della Rovere, until in 1631 it passed to the Papal States. From then on it was a prison.

Cagliostro, its most famous prisoner

Giuseppe Balsamo, known as Count Cagliostro, was born in Palermo in 1743 and became an alchemist, healer and freemason famous at courts across Europe. The Inquisition arrested him on 27 December 1789 and locked him in Rome’s Castel Sant’Angelo, which I cover in Castel Sant’Angelo. On 7 April 1790 he was sentenced to death for heresy. Pope Pius VI commuted it to life imprisonment in San Leo.

He was first held in the Treasure cell, the safest and dampest in the fortress, and then in the Pozzetto, where he died in 1795. Stepping into that cell is, for me, the most powerful moment of the visit. A papal physician of the time wrote that those dungeons were not prisons but graves, and once you see them you understand why.

What to see in the village

Down in the village are two Romanesque churches I wouldn’t miss. San Leone Cathedral rises on a bulge of rock as if on a pedestal, was reconsecrated in 1173 and keeps fragments of an earlier church, such as the winged lions now propping up a column. The pieve of Santa Maria Assunta is the oldest religious building in the Montefeltro, and the municipal website likens it to a stone ship run aground on the rock. Both open daily 09:30 to 12:30 and 14:30 to 19:00.

The civic tower beside the cathedral is usually closed and only opens for festivals and events. Palazzo Mediceo houses the Museum of Sacred Art. And from any edge of the village you look down the Marecchia valley to the sea. Dante came here and mentions it in the Divine Comedy, as did Saint Francis, who according to the region received the gift of Mount La Verna in San Leo.

Hours, tickets and getting there

Until 31 October 2026 the fortress opens 10:00 to 18:45 on weekdays and 10:00 to 19:45 at weekends and on holidays, with last entry 45 minutes before closing. Tickets are €11 from age 26, €2 from 18 to 25 and free up to 17. On a Saturday, Sunday or holiday you can pay €14.50 and add the stronghold and museum in Verucchio, which is what I’d go for.

By car, leave the A14 at Rimini Sud and follow the SS72, the same road as for San Marino. By public transport you go from Rimini on line 160 to Pietracuta and change to the Valmabus, which only runs on weekdays. In summer the San Leo Experience excursion bus ran from the Riviera on Thursdays, but its 2026 season ended on 10 September.

San Leo is 22 km from San Marino and about 30 from Rimini. How to combine it with the rest is in day trips from San Marino.