The ride from Skopje, Macedonia to Sofia, Bulgaria is an easy five hour bus ride. Of course, one hour of the trip is taken up at the boarder crossing (where your passport disappears twice into a darkly shaded building, but thankfully is returned) and another hour is taken by the time difference between the two locations. This places the actual driving time between the two cities at a quick three hours; I hopped on the bus early on a Sunday and found myself in Sofia by mid-afternoon.
Despite their proximity, Skopje and Sofia have distinctly different feels. Sofia has an interesting Thracian/Roman heritage with an Ottoman legacy and communist influence. The buildings are built in a variety of architectural styles, colors, and dates of conception. Some key sites I visited during my walking tour included the famous Alexander Nevsky Cathedral, Ivan Vazoz National Theater and the Church of St. Petka and the Saddlers. The main metro station is built into the ancient ruins of Serdika, a city built in 2000 BC by the Thracians who thrived in the area. While it's initially strange to walk by ancient bath structures on your way to catch the train, you soon get used to stumbling upon historic treasures. Much of Sofia was bombed during WWII, Bulgaria was on the side of the Axis powers, but a large number of important sites survived or have been rebuilt. Despite the controversial history in WWII, Bulgaria prides itself on being accepting of cultures and religions. The epitome of this is shown in the 'Square of Tolerance' where a synagogue, a mosque, a cathedral and an orthodox church exist within several hundred meters of one another.
The people I met in Sofia were exceptionally warm and welcoming, and the food incredible! I recommend checking out Manastirska Magernitsa for a traditional Thracian and Bulgarian meal. My visit to Bulgaria was too brief and I'd definitely like to come back. If I do, I plan to head inland to the medieval city of Veliko Tarnevo and the Dead Sea. I always find the problem with traveling is that you're never crossing places off your bucket list, you are continually adding to it.