After living in Damascus, Syria for a year my favorite place in Syria is the old town. When native Syrians hear this the first thing they always say is "Of course, you're a foreigner." But anyone who appreciates art and culture would feel the same way.
Damascus is the oldest continuously inhabited city in the world but in my opinion all the charm is in the old town. I can spend hours wandering along the meandering alleys which also happen to be two way roads lined with shops on both sides (FYI those alley/roads aren't much wider than the average four door car.)négligé! Yes, in syria! Panties and bras that fall when you clap, thongs with cell phone holders, bras with bird nests, tassels, feathers, zippers they've got it all! Apparently conservative Syria has the kinkiest lingerie and there's even a book about it--The Secret Life of Syrian Lingerie. I think it's just WEIRD.
For food in old town I like Naranj for a traditional meal or Pizza Reef for on-the-go thin crust Italian pizza. There's also a funky dimmed-light bar named After 7 that reminds me of a bar/coffee shop in Houston called Agora. (maybe that's why i like it ;-)) At After 7 you find a good mix of native syrians and foreign exchange students living in Syria to study Arabic. Apparently on Friday nights people gather at the little park in front of After 7 to play the guitar and sing.