8. The Hamptons
Movies: White Chicks, Weekend at Bernie’s, Something’s Gotta Give
Why You Should Go: Any time the Hamptons are in a movie it means access to mansions, boats, and beaches -- and everyone is too rich to have a job, so there are always cool people to hang out with.
Why You Shouldn’t Go: The only women you can be certain aren’t Wayans brothers in disguise are your mom and your girlfriend, and Jack Nicholson will sleep with both of them.