Plovdiv, Bulgaria's second largest city, is the eight oldest continuously inhabited city in the world and the third oldest in Europe. It was first settled in 4,000 BC. Not surprisingly, the city is rich with archeological, cultural, architectural, and artistic treasures.

Less than a hundred miles southwest of Sofia, it can be easily reached by car, bus or train. In 2019, Plovdiv will play the important role of being the European Capital of Culture for a year. You may as well beat the crowds and visit it now.  

Plovdiv is a city made for slow travel. There is no need to feel compelled to explore in a rush manner - ever. The city is compact, everything can and should be reached by foot. You can get a great sense of what the place is all about just by engaging in some deliberate coffee indulgence and people watching at a series of cafes around town. Here is what I propose, based on my recent visits to Plovdiv:

Stay: 

Ramada Plovdiv Trimontsium is a solid, if slightly uninspiring bet. The location is perfect, the rooms are basic but comfortable and the breakfast is a real treat. I also enjoyed spending time by the pool last summer. 

Odeon Hotel Plovdiv - more a B&B than a hotel. I’ve spent a few perfectly enjoyable nights there. 

See:

Main Street - the so called “Glavnata” is a long stretch that spans a sizable part of the city. It is entirely pedestrian, lined by trees and handsome old buildings. There are two Roman remains sites that can be experienced while exploring Main Street. You could literally sit on ancient Roman stairs with a gelato in hand and contemplate the meaning of life and history. O tempora! O mores!

The Roman Theatre - possibly the best Roman site in Europe after the Colosseum. I kid you not. 

The Old Town - a must see and a veritable delight. Beautiful history filled houses, several of them turned into museums. 

Kapana (The Trap) - Kapana is a newly renovated part of the city center. It used to be the craftsmen district, now it's home to a multitude of cafes, bars and shops with a great leisurely vibe. 

The City Art Gallery - small but full of artworks that truly convey a sense of the city’s more contemporary history and culture. 

Go for a walk or a run around the Rowing Channel (Greben Kanal) - Rowing Channel | Health & Leisure | Plovdiv

Savor:

Dolce Fellini Cafe - I rarely start a morning in Plovdiv without a visit to Dolce Felini. Great coffee made from carefully curated beans and sinful pastries. 

Hemingway - simply my favorite restaurant in Plovdiv. I am not arguing it’s the best but the location, food and people watching are excellent. 

Pavaj Restaurant - imaginative selection of traditional Bulgarian dishes with a contemporary twist.

Stop by a farmer's market - Plovdiv is a major agricultural region and exploring its produce is a treat for all senses. Buy a juicy peach or a gorgeous heirloom tomato - the taste and flavor will haunt you pleasantly for years to come.... 

Shop:

Plovdiv is not necessarily a huge destination for shopping but if you are interested in something that would remind you of your visit, I would consider getting some souvenirs from the shops in the old town or in Kapana. You will find some wonderful artisanal works there.