An hour north of Fátima is the university city of Coimbra. Fortified on its hill, overlooking the Mondego River, in its medieval heyday, this was Portugal’s leading city.

In the Middle Ages, when Muslim Moors controlled Portugal, this was the dominant city. And then, for an entire century, it was the country’s capital. Only later, when Portugal was becoming a maritime power, did the port cities of Lisbon and Porto become more influential than Coimbra.

The city was established by the ancient Romans at a strategic bridge that crossed the Mondego River at this point. Today’s bridge leads to the main square, a great place to begin your Coimbra visit.

Coimbra is a delight on foot. The pedestrian-only main drag is perfectly straight—an indication that it survives from ancient Roman times.

It ends at another people-friendly square facing the Church of Santa Cruz.

To be sure I get the most out of my travels here, I’m joined by my friend and fellow tour guide, Cristina Duarte. Wherever you’re traveling, you can find private guides listed online and in guidebooks.

It seems like I’ve got friends all over Europe, doesn’t it? But you know, I’m paying them to be my sidekick. And you can, too. I find hiring a private guide to be money very well spent.

Rick: OK, so, the gate is just this way, isn’t it?

Cristina: And this is the gate of the old city.
Rick: Of the old city. What was the name?
Cristina: Medina. Arco de Almedina.
Rick: “Medina” is an Arabic word.
Cristina: Is an Arabic word, and reminds us that we were ruled by the Moors for a couple of centuries…
Rick: OK.
Cristina: …and defense was very important.
Rick: So…
Cristina: That’s why the street, you see, it’s not straight. It forms an angle.
Rick: Oh, OK.
Cristina: And if you look up, you have mata-cães…
Rick: Mata-cães.
Cristina: … meaning “kill the dogs,” because it was meant to throw the stones to the enemies.
Rick: Oh, no!
Cristina: Yeah.
Rick: “Kill the dogs” — I don’t want to be here.

Rick: What’s this?
Cristina: This is the Old Cathedral.
Rick: How do you say that in Portuguese?
Cristina: Sé Velha.
Rick: Sé Velha.
Cristina: It’s a 12th-century cathedral, Romanesque.
Rick: So, Roman — ’cause you’ve got the round arches.
Cristina: That’s true.
Rick: Now, it also looks like a fortress. Look at the crenellations up there.
Cristina: We were on the times of the Moors and Christians fighting for the same territories.
Rick: So they were still worried about the Moors?
Cristina: Oh, yes. They were. They were.
Rick: So this is kind of a double building — a church and a fortress?
Cristina: Yes.

We’re dropping into a tiny theater to enjoy a fado performance. Fado is a uniquely Portuguese style of music — soulful and nostalgic. While most fado is sung by the women, here in Coimbra, it’s the men. The songs are serenades of love — usually sad, unanswered love. These troubadours have long provided the soundtrack for life here in Coimbra.