Boston

It's a homecoming for Jay! Join him and Sean for a hard-drinking tour of one of America's oldest cities. The first night goes a little crazy when they meet up with Jay's brother Adam at Drink in South Bay. Before they know it, they're shooting dice in the kitchen and swigging gin. Luckily for Sean, the Monday morning brunch at Trina's Starlite Lounge is loaded with hangover cures. Next stop is Bleacher Bar, where patrons can take in a baseball game from below the seats at Fenway Park. And finally, it's Hong Kong in the Fanueil Hall marketplace for Scorpion Bowl races with some of Jay's old friends. Will he ever leave again?