It has been awhile since I've live in Jacksonville...the Casbah in Avondale has a good wine selection--although *not* quiet on a Friday nite. European Street (the one on Park St) was always my friends' pick. They, by far, have the best beer selection in Jax. Wall Street in 5 Points is a good watering hole. You'll see everyone from college professors to tattoo artists in there. I've never been to Ragland's (also in 5 Points), but was always a big fan of Fuel (same owners). Unfortunately I think most of my old favorites have closed.