
Ill-prepared. It’s a feeling you despise, especially while traveling. You’re usually the researcher, the strategist, and the planner all at once. By the time you reach a new destination, it normally feels like an old friend. Not Plovdiv. You, embarrassingly, know very little about Bulgaria’s second-largest city. Now you’re going to have to catch up very quickly.
Your first trip to Bulgaria was supposed to be fast. You thought you’d make a quick stop in Sofia, the modern capital, during a larger tour of the Balkans. Sofia was fun. You found domed churches, green parks, and yellow cobblestone streets. You also kept hearing about Plovdiv. The City of the Seven Hills sounded older, prettier, and cooler than Sofia. Since it was only two-and-a-half hours away on the train, you made a few adjustments to your itinerary. Less than 24 hours later, you arrive at the Plovdiv Central Railway Station.
You head to your unremarkable hotel first. Plovdiv’s accommodations desperately need an upgrade. Boutique hotels don’t open in unknown cities, though, and this one has remained blissfully under the radar. That means the ancient ruins, the romantic Old Town, the hipster bohemian quarter, and the lookout points from those seven rocky hills aren’t overrun with tourists. Neither are the restaurants that came highly recommended by your seatmate on the train.

Just because Garden-Restaurant Philippopolis isn’t filled with visitors doesn’t mean it’s easy to secure a table. Since locals love the restaurant in the Philippopolis Art Center, you grab one of the last available reservations. The early timeslot allows you to take in the view. The historic building sits on the edge of the Old Town overlooking Kapana, the trendy neighborhood. The Plovdiv Roman theatre, one of the best-preserved ancient theatres in the world, is just steps away. The restaurant’s interior is ornately decorated with Tiffany stained glass and crystal mirrors. It leads to a shaded terrace along an ancient Roman wall. Add soft music, the setting sun, and a glass of local Mavrud wine for a stunning introduction to Plovdiv. The food, which is fresh and seasonal, almost doesn’t matter.
It’s just as hard, if not harder, to get a reservation at the second restaurant. A bit more time (read: not the day you arrive) certainly helps, though. Pavaj is your excuse to explore Kapana. “The Trap” is considered the creative heart of Plovdiv. Sweet-smelling flower shops, little jazz bars, and funky cafes line its tight streets. Cozy restaurants like Pavaj do, too. Pavaj’s young owners keep it simple. Most of their vegetables (think rare heritage tomatoes) come from their own garden outside of the city. The meat, including what’s used in their famous meatballs, is sourced from their neighbors. Even the wines and the rakias (the brandies) they serve are more regional than national. You book another reservation before you even leave the restaurant.
For someone who wasn’t prepared for this trip, you’re certainly eating well. It looks like great restaurants and food are the keys to getting to know Plovdiv. Thankfully, you caught on quickly.