Being in a new city where you don't know anyone or anything can be intimidating. Here are some strategies that I use to familiarize myself with urban locations.
  1. Follow a crowd
    If there's a crowd of people, follow them. They're probably on their way to have a good time.
  2. Train tactic
    Get off a random stop on the train, make a left, walk 2 blocks, make a right, walk one block, make another left, and go into whatever the 4th building is (this has been a problem for residential establishments. They don't always appreciate spontaneous company).
  3. Scavenger hunt/dinner
    Go around the city trying to find coins on the ground. Once You've gotten $0.55, you can take that right over to Jimmy Johns and get a loaf of day-old bread (this one is a LOT harder than it seems. No one drops coins anymore. Also, remember to look up from the ground every once in a while).
  4. Directions
    Yell directions at people even if they didn't ask for them
  5. A new Dunkin
    Instead of going to the same Dunkin Donuts that you always go to, just keep walking in any other direction until you find a different one (this can work with any food chain).