Every year some of my friends who live in the city have a "New York tourist Day" - they've been doing it for three years.
First, the break up into teams - it's a game. You start out at a bar at 10am- everyone drinks cosmos and appletini's - anything you'd see on Sex and the City. Then you're let loose on the city, you're awarded points based on the pictures you take documenting the shenanigans of the day.
Bonus points for: Statue of Liberty visit, Top of the Rock, Confusing the Empire state and Chrysler buildings, Time Square, Brookyln Bridge, pictures with the stereotypical street performers, going to a cheesy NY gift shop and going to Starbucks.
You must dress like a tourist: shorts, tennis shoes, goofy hat, fanny packs, "I heart NY" tees (We buy them at a discount as a group the day before), cameras. You have to walk slow, get "lost" and ask for help, and take obnoxious pictures with the subway poles. You also have to take a double decker tour bus ride.
The more outrageous team wins dinner when everyone meets up at the end of the day - at Olive Garden.