4 Medieval Cities You Shouldn’t Miss Visiting

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Medieval cities are among the most interesting sights in Europe. They tell a story of a past that highly defined the way Europe developed as a continent, in addition to smaller stories of the families and events that led to the creation of each city.

The truth is that Europe counts with thousands of medieval cities, but some do stand out from the rest.

What follows are my top four medieval cities visited during my round the world trip, and the ones I believe you shouldn’t miss visiting in your lifetime.

Dubrovnik, Croatia

Before the series Game of Thrones (GoT), Dubrovnik had a name for itself as one of the most charming cities all over Europe. Now, thanks to GoT, it is an “it” place for fans of the series looking to experience a bit of Westeros in real life.

Located in the Adriatic Sea in Croatia, Dubrovnik is one of the most attractive and romantic cities you’ll ever visit.

As you walk through its cobblestone streets, you’ll get a glimpse of how this city developed itself through maritime trade, the history of its architecture, and the purpose of its fortifications and how they’ve helped the city throughout its lifespan.

The latter is, in my opinion, one of the most impressive architectural sights of the entire city – running almost two kilometers around the city and reaching up to six meters in thickness.

There are also a few interesting details about Dubrovnik that shouldn’t be missed, like its Arboretum Trsteno, the oldest arboretum in the world dating back to before 1492; and the third oldest European pharmacy (yet oldest still in operation), which dates back to 1317.

Grazzano Visconti, Italy

Before I go over the details of Grazzano Visconti, I have to say that this is a quasi-real medieval village. While the village looks and feels like an authentic middle-age destination, it was built by the Duke Giuseppe Visconti di Modrone in the early 1900s, just 11 kilometers away from Piacenza in Italy.

Still, there is a lot of history to be witnessed in Grazzano Visconti. Documents tell of the early origins of the village, back in the 1300s, in the form of a simple community.

Towards the end of the 1400s, Gian Galeazzo Visconti (Lord of Milan) granted his illegitimate daughter Beatrice, the former wife of the nobleman Giovanni Anguissola from Piacenza, permission to build a castle.

This castle proved to be the scene of many battles for several centuries, due to the feud of the Anguissola nobles.

When I visited it back in 2013, I felt like I was in one of the best preserved medieval towns in the world. Every detail, every brick, and every corner told a story that felt like it was still under development, and very alive.

For example, you could see highly detailed architectural elements like the stone and pink marble well with its wrought iron lid, decorated with the Visconti snake; or the several holy images and statues placed all over the village, making reference to the strong Catholicism found in Italy.

You can even see the Madonnas found today in the village, first created in 1947 as an offering from the Grazzanesi for having preserved the village from the bombings of WWII, which ravaged the nearby villages.

Grazzano Visconti has very attractive and harmonious architectural ratios and scales that make you feel like in a very cozy environment.

The details go on, but in general, this village feels like a dreamscape in a timeless bubble.

Toledo, Spain

Whether it is because of the old atmosphere and former European capital aura, or just for the fact that it was my first time entering into an almost perfectly preserved fortified medieval city, Toledo is another medieval town I fell in love with the moment I set foot in it.

You can get lost in its winding and hilly streets, which is the perfect excuse to enjoy hundreds of years of history shared by its buildings, cobblestones, walls, and even through its people.

Toledo became a fortified city under Roman occupation – its location and the Tajo River made it an ideal fortress, and from that moment on, the city became one of Spain’s most important political, economic and cultural centers.

During the 13th century, Toledo became one of the few places in Spain where Moors, Christians, and Jews managed to live together and tolerate each other more or less peacefully.

This led to a singular combination of styles and cultures that gave the city its unique characteristics.

Toledo might be small, but it concentrates a lot of history within its fortified walls.

Places like Plaza de Zocodover and the Alcazar of Toledo – a stone fortification located in the highest part of the city and used as a Roman palace in the 3rd century – and the Cathedral of Toledo, are not to be missed.

Kotor, Montenegro

Even though my visit to Kotor was quite fast, that short time spent there made a lasting impression and created a need in me to go back to explore more of the city.

Kotor is a fortified town on Montenegro’s Adriatic coast, characterized by winding streets and squares and Romanesque churches, including Kotor Cathedral.

Its walls, which were built between the 9th and 18th century, arch steeply up the slopes behind this dramatically beautiful town.

At night, everything is spectacularly lit (including the walls), making the city feel like something you must admire both from inside and outside – as a museum item, more than a city itself.

Its marble streets are like a labyrinth lined with churches, bars, shops, plazas, and restaurants. It is a romantic city, for sure, whether that romance is with that special someone or with the history and architecture of the place.

Make sure you’re renting a car in Montenegro to explore beyond Kotor. The country is stunning!

See why you shouldn’t miss visiting these medieval cities?