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Discover San Leo

San Leo is one of my favorite hill towns in all of Italy.

I was completely stunned the first time I came here. I couldn’t believe that such a place could be so little known outside of Le Marche and Emilia-Romagna - it lies on the border of the two regions. Now I'm a regular visitor, and many of the tourists you will meet here are repeat visitors. Once you have been here, you will find it difficult to resist the longing to return.

Approaching this gorgeous stone village, sprawled across its clifftop, is a breath-taking experience. From a distance, the town appears as a miniature version of the nearby Republic of San Marino, but San Leo is the better of the two—smaller and far less touristy.

It really feels like you have stepped back in time, and unlike Florence or Venice, the lack of tourists here enhances that. The village is almost exactly as it must have been a thousand years ago.

Photo by Jim DeLutes

Where to Stay

The Agriturismo Eutopia is not a hotel but a wonderful country farmhouse (called an agriturismo in Italy). The setting is beautiful, and the location is perfect for exploring both San Lea and San Marino as well as elsewhere in Le Marche and Emilia Romagna. You will, however, require a car; this is the car rental company I use when traveling.

What to See in San Leo

The Castle

Towering over the town is the medieval castle. It is a bit of a walk up the hill to the castle but well worth the effort, and the views are stunning.

It is not hard to imagine prisoners of the papacy being brought into the castle, which served for centuries as a prison. Count Cagliostro is the most famous of the prisoners who were once kept here. Imprisoned for heresy, his cell, adorned with admirers' flowers, is nasty.

From the window, he could only see the 9th-century church, this was deliberate on the part of his captors, who believed it would ensure his repentance.

The torture chamber in the dungeons bears testament to the cruelness of those medieval times. It is only too easy to imagine the screams of centuries of prisoners echoing out through the pitch black of this hell. To be honest, it gives me the creeps, and some say the dungeons are haunted. It is believed that if you spend the night here in total darkness, you may feel a cold breeze raise the hairs on the back of your neck, hear a blood-curdling scream, or even a manic giggle. For some reason, spending a night in these dungeons is not on my to-do list.

Some of the castle dates back to Roman times, but most of it is the work of Francesco di Giorgio Martini, one of the finest Renaissance military architects.

Castellans and even those knowing little of medieval military history will be amazed at the complicated and barbaric defenses of this castle or fortress.

Piazza Dante

Umberto Eco, one of Italy's greatest writers, called San Leo the most beautiful city in all of Italy. He loved the castle and the churches, but more than anything, he loved Piazza Dante. It is in Piazza Dante that poets, artists, and writers have passed by and fallen in love—not just Umberto Eco, but Dante Alighieri too.

The center point of the piazza is the fountain, and it is here that I have had some great conversations with friendly locals eager to share their passion for their town with visitors. Use the fountain to top up your water bottles and your list of stories to tell your friends when you return home.

Palaces and Churches

The 16th-century Medici Palace houses the Museum of Sacred Art, a library, and the local tourism office, which proved to be very helpful and knowledgeable.

The two churches you'll want to visit are:

The 9th century church of Santa Maria Assunta and the 12th century Cathedral of San Leone.

Visit too the Torre Civica, a tower that was probably built around the 11th century although, according to the tourism office, there is some doubt/debate about that. I am sure the views from the top must be amazing, however, except for festival days it is closed to the public.

Lunch/Dinner in San Leo

I cannot get enough of Ristorante Osteria La Corte di Berengario II. It is everything I love in a restaurant: great local food made fresh with local ingredients but without any pretensions; everybody makes you feel welcome and relaxed; and nothing is too much trouble for the staff. I ate here the first night I arrived and never bothered to try anywhere else. I love this place.

Where is San Leo

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