San Marco Boulevard, San Marco
Old-timey shops and whatnot, walkable. Nice. Pretty.
Park Street, Riverside
Bars and nightlife. Where the cool kids go to be seen, at least the ones who maybe also think they are intellectuals.
St. Johns Avenue, Avondale
Fancy area with neat shops and restaurants.
Bay Street
So maybe a couple of bars and drunk people wandering after a game or concert.
1st Street, The Beaches
So there's a big gap between Atlantic Beach and Jacksonville Beach along 1st Street, but it's bike-able. AB Town Center on Atlantic is a neat little area. Jacksonville Beach is perfect for trust-fund kids out carousing. And the beach is a few steps away.
Town Center Parkway
Ha ha ha ha ha! The St. Johns Town Center is so frustratingly horribly planned that it's amazing to me that it has remained so popular. All the fancy stores you could want packaged in an un-walkable, nearly un-driveable outdoor mall. You can sit in traffic on Town Center Parkway and see most of the stores, wishing you had the kind of job that could afford you the time and that Audi S8 parked at Nordstrom's during normal work hours for the rest of us.
Vermanth Road
I was told by a friend that Vermanth Road in Arlington is the only so-named street in the United States. If that's true, then only about 65 households live on a street by that name, and that's pretty cool. That said, it's just a normal few blocks in Arlington, so it may not seem that cool unless you know how unique it is.
Moncrief
I once heard someone from Jacksonville talking to someone from Atlanta, and the guy from Atlanta said something about Moncrief, so the dude from Jacksonville was like, "You know Moncrief?" And the cat from Atlanta was all, "People all over know about Moncrief." I guess that's cool? But I wouldn't really suggest you go and check it out. Just ask someone.