Travel time: 45min
What to bring: Your curiousity
Best for: Hipsters

You would think to find the most expensive home in the U.S. somewhere in the Big Apple. But surprisingly enough, it's about 45 minutes North in Greenwich, Conn. This affluent city along the Long Island Sound is just a short train ride from Wall Street, making it a choice location for wealthy city dwellers to escape to. While you're there, take a stroll through the series of perfectly manicured neighborhoods, or pack a picnic and head out to the Greenwich Point peninsula. Hell, if you start feeling homesick, you can even catch a glimpse of the Manhattan skyline on a clear day to remind you just how close you are to the city.