Small and beautiful: the italian fortress of San Leo

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Buckle up to travel in time with me while reading this post. San Leo was hype when christianity was not yet a thing within (now) Italian territory. Enjoy!☀️

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San Leo fortress

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The famous Italian writer and philosopher, Umberto Eco, most famous for “The name of the Rose”, once said that the most beautiful city in Italy was San Leo. We know the recommendation of this author, being Italian and all, MAY 🙈 be biased. But when visiting this place we found he was not far off.

San Leo is a medieval town located in Montefeltro region in Italy, and sits right across from San Marino, the "oldest country in the world".

When traveling in the area, most people visit San Marino, a more notorious and famous destination. But is it also more beautiful? No!!!

Sorry, San Marino. We apologize. But dear reader, you should know we are not being creative when bringing up this dispute. The feud between the two cities: San Marino and San Leo is historical... And today we add some spice to this contest by telling you all about our weekend trip to San Leo, and why you should definitely add it to your bucket list.

The earlier constructions in San Leo suggest that the town was already building its first settlements as early as the third century BC. Its origin and development is closely tied to the expansion of the Roman Empire and Christianity. The buildings to check out in the central part of town are: Palazzo Mediceo, and the Church of the Madonna di Loreto among others. The center where you find these attractions preserves a romanesque style, characteristic of the renaissance period.

Madonna di Loreto Church

The main church, were the wedding was taking place. You can see small the white flowers at the entrance.

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@aurzeq and I took a car to arrive at San Leo. Parking lots are available close to the town center. Access by public transport is tricky and not recommended. Some more adventurous visitors take bikes. We saw not one, but a lot of them on our way up. Way up. @aurzeq told me he did it with a buddy once in the good old days... haha… 🙈😂

You have to be well trained to get up. I am telling you. Just as San Marino, San Leo sits on top of a hill with a very characteristic steep cliff that overlooks the Marecchia Valley. If you search online for the town, this will probably be the first image to pop up. From the town center, to access the fortress you will have to take a walk up, as it is located out of the main urban area as it was built and used to defend the settlement in the Middle Ages and then also Renaissance. The location is strategic and thus has been the site of military events across the centuries.

Other takes of the fortress from afar

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Other takes of the fortress from afar

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Once we left the car parked, @aurzeq walked around town. If you are in a hurry, in 30 minutes you can be done as it is small. But take your time, my friend, because it is breathtaking. Next pictures are just wondering between the houses and buildings in town.

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Tourists in San Leo are not from abroad, but mostly Italian, and this town has such a charming and romantic vibe to it, couples chose it as a wedding venue for their celebrations. The town is so small, the wedding taking place while we were there was the parade of the town. A lot of customers in the bars were from the wedding and so it was funny to look around and find somehow you were totally underdressed.

The bride making an entrance to town

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You will border the cliffs with the car, coming up. A beautiful door is the car entrance to town.

@aurzeq walking through the door too, now from the other side.

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You can tell San Leo is cute and beautiful not only for its attractions, but because buildings are also very well kept. The town is clean and ready for visitors with a well equipped tourism office, a few restaurants and services to go up, up, up towards the fortress. If you don’t want to walk - which is for free.

This we took from the tourism office. Other resources are available to you if you prefer!

Square

Square with the Parish Church taking center stage. The tourist office is behind the tree to the left.

The town square is called Piazza Dante, and it may be due to the fact that Dante walked its streets around 1306. It is likely that the “Sommo Poeta” was familiar with the location because of his friendship with Ugoccione della Faggiola, the lord of the neighbouring town of Casteldelci, and because of the description he provides of it in Canto IV of Purgatory:

“Vassi in Sanleo e discendesi in Noli, montasi su in Bismantova e ‘n Cacume con esso i piè; ma qui convien ch’om voli”.

The Divine Comedy compares the location where the poet is, to royal locations renowned for their harshness in order to convey a difficult climb that is exhausting and impervious. San Leo's cliff,among others, is mentioned because of how difficult it is to reach it.
A big painting is a reminder of this important Italian figure. You will not miss it if you are walking around town. It is big and red covering all of a wall.

Dante painting in the main Dante Square.

Another thing you will see when walking is the parish church. it is the oldest christian building of the region. It stands close to the cathedral, another very old building. Both available for visits (and weddings).

Parish Church from the inside.

We tried the local food, and among other things we recommend the Cannoli “Cagliostro”, a sweet typical from Sicily, but here readapted in honor of one of the most important historical figures of the city, Count Cagliostro.

Cagliostro portrait borrowed from here. Did you know? Alessandro Count of Cagliostro, alias for Giuseppe Balsamo, was one of the most mysterious and intriguing adventurers of the Age of Enlightenment. Cagliostro's many activities have always been mysterious, which serves to maintain interest in him also now. His reputation as a healer and alchemist spread to the most prestigious courts in Europe, from London to St. Petersburg, where he was able to develop relationships with influential people like Schiller and Goethe.

Cagliostro was taken into custody by the Holy Inquisition on December 27, 1789, and given a death sentence. He was forgiven by Pope Pius VI, and his sentence was changed to life in prison to be served in the Fortress of San Leo. He was imprisoned there in an empty cell that he was lowered into through a trapdoor in the roof, where he died in 1795. The San Leo fortress was for many years a famous prison.

We enjoyed the views, we walked up and down and want to tell you, if you have time and already decided to go to San Marino. Make a stop here too cause it is totally worth it! Now a few pictures with the view from San Leo to the valley.

Our final words on the feud of the 2 cities:

As it turns out, we searched and romed for details of the feud between the two towns people have been telling us about. No easy information is ready for access. So maybe next time we visit, we will go for one of the tours because we are all in for the gossip. We have found out so far, that Marino and Leo were friends and responsible for the spread of christianity in the region. We suspect the problems between towns have to do with later periods in which powerful families, such as Montefeltro and Malatesta contested for territory and dominance in the area. But as I write this, I do not know. We will have to further our investigation on the matter. If you have any news, let us know in the comments below.

Have a great one, friends! A pleasure to share our adventures with you!

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Talk to you soon!