I’m going to let you in on a little secret. Plovdiv just might be the highlight of Bulgaria (Maggie would disagree and say it’s Varna, I’m sure, but she’s biased). It ends up being my favorite city in the country, and my second favorite city in all of eastern Europe (after the city where I studied in college, Pecs, Hungary). The atmosphere is relaxed and I could sit at one of the cafes, or in the nearby park all day, drinking coffee and reading. In fact, the first several hours I’m here, I do just that!

As soon as I arrive at the bus station, I check into my little hotel and head out to wander the streets and orient myself to the city. Plovdiv is the second largest city in Bulgaria, after Sofia, but from this area of town, you would never guess it.

It’s about a 2 hour bus ride from Sofia to Plovdiv and I left early, so I stop at a little cafe to have some coffee and a snack.

Not pictured above is the guy playing the saxophone up the street. Sitting here, drinking coffee, reading my book and listening to the music, I think I may never go home. Can every day be like this please?

Eventually I decide explore the town a bit more and come across these Roman ruins. It was once a forum and the largest in Bulgaria. I’m sure it’s nothing to the people here, but I find it so fascinating that you can turn a corner and just happen upon ruins thousands of years old.

I’m only in Plovdiv for one day, but it’s enough to see what I want to see. The free walking tour starts at 6pm so after seeing the city a bit on my own, I decide to spend a few hours in the park, relaxing. It’s the Bulgarian thing to do!

Finally it’s time to join the tour! Similar to the tour I took in Sofia, this is Free Plovdiv Tour. They meet in front of the Municipality Building by the fountain on Main street at 11am and 6pm in the summer, 2pm in the winter. I’m here right at the end of September so I luck out and get the 6pm tour. It ends at the top of the hill overlooking the city, so I’m hoping for some great sunset views.

Our first stop is the statue of Milyo the Crazy. He was a resident of the city who wasn’t all there, but the citizens found him charming and good natured. After he passed away, they erected this statue of him. Many residents still remember him, and it’s considered good luck to rub the statue as you walk by.

At the end of the pedestrian promenade is part of a Roman stadium, the Odeon. It actually runs the entire length of the street (the one in the pictures at the top of this post) and once held nearly 30,000 spectators. And that forum I came across earlier is also part of this. Eventually, it was covered up to build the road and buildings, but this end was excavated and is now used to stage events. We luck out and get to watch a traditional Bulgarian singing performance. I love how colorful their costumes are!

After watching awhile, we start our trip up the hill to the oldest part of Plovdiv.

About halfway up, we stop at this ancient Roman theater overlooking the city. The views from here are incredible! And I love how, just like the stadium below, the theater is still in use today. According to Wikipedia, it’s also one of the best preserved Roman theaters in the world. Pretty cool!

I wouldn’t mind living in this house with this view. It certainly wouldn’t suck, though those rocks being tied back seem kind of sketch for the people below.

We continue further up the hill to see all the cute medieval homes. They are so well preserved, it’s easy to imagine what it must have been like to live here hundreds of years ago. I doubt much has changed.

One of the more iconic sites in Plovdiv is the eastern fortress gate, Hisar Kapia. This whole area definitely makes me feel like I’m back in the middle ages. Well, except for those modern cars.

As the sun starts to set, we make our way to Nebet Tebe, the highest point in Plovdiv. It’s these ruins that give Plovdiv a reputation for being one of the oldest continually inhabited cities in the world. Prehistoric remains have been found all over the city, but the oldest were found right here. And who can blame those ancient people? The views are great!

OK, maybe this isn’t the view those ancient people would have seen, but that sunset would have been. And it probably was easy to defend from high on the hill.

The tour ends here and at first I’m a little worried about getting back down, but it turns out to be really easy – just go down. I stop by the Hisar Kapia gate for a few more photos.

In typical European fashion, people are just getting their nights started. I pass restaurants packed with party goers having a great time, but I slowly make my way back to my hotel. These walking tours are such a great way to get a feel for the best parts of the city and I highly recommend them to anyone who finds themselves in Bulgaria. The guides are enthusiastic and really seem to enjoy what they do. And definitely make sure you check out Plovdiv. I wish I could spend more than 1 day here, but time is limited and there is more to explore!