Continuing my week’s theme of trips through Emilia-Romagna and beyond, I decided to finally check off a small country I’ve always wanted to visit: San Marino! Looking at the map, I discovered the picturesque village of San Leo is just outside its borders, so I leveraged the proximity to add an additional stop. It was an incredibly long day (about 6 hours alone of driving!), but absolutely worth it for the views and cultural heritage.

The drive from our hotel just west of Bologna to San Marino took me all the way to the Adriatic Coast, turning south at Rimini and, an unfortunate toll booth plaza situation later (I accidentally pulled into the lane for EU pass-holders and promptly had to back my way out to the displeasure of the Italians behind me), I was zipping along towards San Marino. It turns out, zipping is exactly the correct way to describe Italian driving – roundabouts are incredibly common, requiring you to “zipper” in and out of traffic as you circle. In addition, the roads are so narrow that you truly zip by oncoming traffic. I do have to say, the “safety” features on my Toyota are completely misaligned to reality and lane assist / centering functions are absolutely more hazardous than not when you’re white knuckling past a dairy truck on a one-lane road with a narrow shoulder.

Unlike some small countries I’ve visited, San Marino is both a “county” and a city – there are a number of small cities in the “country” in addition to the eponymous capital. Once inside San Marino, you have to zig-zag your way up to the hop of the hill where the historic city center and associated sites are, which is not a small feat. After trying to find parking in multiple parking zones and practicing my ability to drive in reverse around tight corners, I finally ascended further up the mountain and was rewarded with both a spot and a view!

I made my way into town, where the locals were just setting up for the day despite it being about 10:30am. I decided to test my luck with the open sites and started making my way up to the closest of the three towers that San Marino is famous for, all of which are situated on sheer cliffs and feature sprawling views.

It is not a climb for the faint-hearted; the town quite literally used to be a lookout fortress atop the mountain. That being said, it’s absolutely beautiful (assuming you can see… which I could for about half the hike, until a layer of fog set in, basically enveloping the entire hilltop). Upon ascending to the “second” tower (according to their naming convention) and having no luck with the view, I decided to try my luck and meandered over the (narrow) pathway that led me to the hike up to the “third” tower. While I could see that the tower was above a sheer cliff, I was actually unable to enter because it was under construction. Womp.

So, I started making my way back to the “second” tower to at least take in some of the view internally.

The “second” tower actually includes most of the fortress, including several lookout points, a chapel and the prison cells. Inside the walls, it’s quite beautiful. My favorite part was hearing a small child shout in German, “IST KANONEN” over and over when he spotted the artillery in the corner (he seemed even more excited to see it receiving some maintenance).

In the far left corner, you can see the small chapel. Inside it wasn’t ornate.

I then walked the perimeter of the fortress walls, which was unfortunately extremely underwhelming given the entire country appeared to be completely enveloped in the cloud at that point. However, I did manage to go up through the tower, which required scaling a scarily steep medieval-style ladder (thankfully it was not ACTUALLY medieval, unlike the ladders I scaled in Romania), which quite literally became metal rebar towards the top as you shimmy through a hole in the rock flooring.

After that harrowing experience, I headed for the prison cells (located somewhere within that block on the left-hand side of the photo below).

Inside was quite interesting – they have a variety of interesting literature about San Marino’s sordid history of torturing prisoners, and interesting insight that the country outlawed the death penalty well before any other Western country (their language). In addition, they’ve uncovered and restored a variety of graffiti present in the prison cells, which was fascinating to see.

Unfortunately, the rain started to pick up, so I (and a few unlucky others) were trapped in the prison for about ~35 minutes waiting for the pounding rain to stop. Given extra time to explore, I took in all the different signage and was amused by the safety rules in particular – it turns out, buildings made in the 1230s aren’t exactly up to modern safety codes (and/or aren’t intended to be used for any manner of Instagram sins)!

Once the rain finally cleared, I made my way down from the “second” tower’s prison and took in some of the initial sights of the “third” tower again. It was much more rewarding this time!

The second tower itself also didn’t look too shabby at this point.

After that, I made my way to the panoramic viewing platform, but sadly, the country was still largely obscured (although I could visibly see the fog starting to lift over the ~15 or so minutes I waited while watching a group of American tourists making fools of themselves taking photos). To make the most of my time, I decided to meander down to some of San Marino’s other sites, which include beautiful winding streets, a basilica, and a stamp / currency museum.

As I meandered the winding streets, pulling out my map frequently to my increasing frustration that a) none of the streets were marked and b) I couldn’t read French, as that was the language I was inexplicably provided, I made a couple stops. First was the basilica, which was relatively nondescript inside and overwhelmed with tourists, many of whom were subsequently told to leave due to dress code violations.

Then, I made my way down to the square that held the Stamp and Currency museum, which was also where I was able to get my passport stamped for 5 Euros (quite literally, they give you a commemorative postal stamp as well as an official “visa” stamp). It’s a very well done museum, although it appeared I was the only patron.

Afterwards, I headed to my final tourist stop, which was the Piazza de Libertad, where many of the government buildings sit.

After that, it was time for lunch – sadly, since most of San Marino is basically a giant tourist trap with all kinds of strange offerings (camo and fake gun shops, every tracky gimmicky gift, perfumes aplenty, I didn’t really expect to get great food. I decided to simply head to the restaurant with the highest review on Google, which ended up being Ritrovo Dei Lavoratori XXVIII Luglio. Hilariously, right after I entered, a giant group of ~30 elementary-school aged kids followed by a group of ~30 seniors with headsets a la museum guided tour strolled in. I prepared to have a terrible meal.

Thankfully, they immediately proved me wrong. I had the set menu for 25 Euro, which included a the local strozzapreti pasta with ragu, a steak, grilled vegetables, delicious cake, coffee and wine. Everything was legitimately delicious, if quite basic.

On my way back to the car, I continued to take in the sites, although the views were slightly marred by clouds still.

From there, I hopped back in the car and meandered my way to San Leo, which is just across the Italy border and, unsurprisingly, is also perched on a tall mountain. As I drove away, I could see the city of San Marino in a distance upon its hill.

San Leo itself is absolutely beautiful, and I see why it is named one of Italy’s most beautiful villages. The fortress itself sits upon a steep hill, and the drive into the medieval village requires you to take a one-lane road carved into the cliffside – it felt a bit like I was saving the princess in Shrek.

Once inside the medieval gate, the village is compact but has significant visual appeal. It has many restaurants, shops and bars – although no one appeared to be out and about.

Before hiking up to the fortress (and I do mean hike, those hills were STEEP and I’m sore two days later despite being pretty acclimated to climbing hills), I visited the couple churches in town. Both were beautiful.

Then, I finally made my way up the trails to the fortress itself. The unmanned ticket-purchasing mechanism was among the most technologically advanced I’ve seen, with a touchscreen purchase interface, as well as a setup that appeared to take my photo and/or biometrics before letting me enter (I have no idea what the purpose was – perhaps identification to ensure I bought a ticket / to prevent reentry?).

The interior of the castle is relatively sparse, although I did find a surely haunted room (that was already creepy enough before I climbed into it and realized there were dried flowers everywhere) and some intriguing / horrifying torture instruments (including some humiliating “masks of infamy”).

Of course, the views were spectacular.

Overall, a fantastic day trip – I’m so glad I finally made it, despite the cloud cover!