Day trips from San Marino: fortresses, Rimini and the Montefeltro

San Marino takes one or two days, and what lies around it is, to my mind, every bit as good. The country is an enclave in the middle of the Montefeltro and the Marecchia valley, a landscape of crags crowned with fortresses that the Malatesta of Rimini and the Montefeltro of Urbino fought over for centuries. These are the five day trips I’d make, in order of what they give me. If you only have a weekend, I show how to fit San Leo in on two days in San Marino.

San Leo, the one I wouldn’t skip

San Leo is 22 kilometres from San Marino, in Italy, on a sheer-sided crag reached by a single road cut into the rock. At the top is the fortress Federico da Montefeltro commissioned from Francesco di Giorgio Martini in the 15th century, and below, in the village, a Romanesque cathedral reconsecrated in 1173 and the oldest parish church in the Montefeltro. Dante mentions it in the Divine Comedy.

What hooks people is the prison. In 1631 the fortress passed to the Papal States and became a jail, and in 1795 Count Cagliostro, alchemist and freemason, died there in a cell known as the Pozzetto. There’s another link I like, because tradition says Saint Leo came over from Dalmatia with Marinus, the man who founded San Marino. It’s all in my guide to San Leo.

The fortress costs €11 for anyone 26 or over, and until the end of October 2026 it closes at 18:45 Monday to Friday and 19:45 at weekends. With a car it’s straightforward. Without one it gets fiddly, as the bus from Rimini needs a change at Pietracuta and the second leg doesn’t run on Saturdays or Sundays.

Verucchio, cradle of the Malatesta

Just 10 kilometres from Mount Titano, Verucchio looks down on the Marecchia valley from its hill. The first Malatesta lord of Rimini came from here, the «Old Mastiff» Dante mentions, and the village stretches between two strongholds, the Rocca del Sasso and the Rocca del Passerello. What makes it unique for me, though, is older. Centuries before the Romans arrived it was a Villanovan centre, and its tombs gave up wooden thrones, textiles and Baltic amber that now fill its Archaeological Museum.

At weekends and on holidays a single €14.50 ticket pairs it with San Leo’s fortress, and that’s my plan, both on the same day, starting with the one further away. I found no official source for a bus to the village, so I’m assuming a car. Everything is in Verucchio.

Rimini, the easy one without a car

Rimini is San Marino’s gateway, and many people only see it from the bus stop. That’s a shame. The Arch of Augustus, from 27 BC, is the oldest Roman arch still standing in the north of Italy, and Tiberius Bridge has carried traffic over the old course of the Marecchia since AD 21 on five arches of Istrian stone. Add the Tempio Malatestiano, the Fellini connection and the nearest beaches to San Marino. If Roman history is your thing, the Surgeon’s House in the centre keeps a 3rd-century doctor’s home with a set of surgical instruments described as unique in the world, and it’s €7 with the City Museum. The Bonelli bus takes 55 minutes and costs €7, as I explain in Rimini to San Marino. The town itself is in Rimini.

Urbino, if the bus is running

Urbino is the city of Federico da Montefeltro, the same man who took San Leo, and his Ducal Palace now houses the National Gallery of the Marche. The problem is getting there. Bonelli’s Rimini-San Marino-Urbino bus only runs in winter, Monday to Friday, following the Marche school calendar, and must be booked. It costs €7.50 from San Marino. In summer, you either drive or you don’t go.

The Montefeltro by car, with a good table

The Montefeltro is a historic region split between the Marche, Emilia-Romagna, San Marino and Tuscany, and San Leo gives it its name. If you’re driving and enjoy your food, two towns have tables in the Michelin Guide, Pennabilli, with the one-star Il Piastrino, and Novafeltria, with Da Marchesi and its Bib Gourmand. There are none inside San Marino, as I explain in where to eat in San Marino.