Visit Sinatra's Hometown
Credit: Stephen Hilger / Bloomberg / Getty Images

Before the popped-collar crowd turned Hoboken into frat row, Frank Sinatra ruled this tough little town – and his legacy lives on. Your first stop should be Dom's Bakery, where the bread is so good Ol' Blue Eyes had it flown to California. After that carbo-load, walk along the water through Frank Sinatra Memorial Park, before ordering a glass of Italian red at Leo's Grandevous – a neighborhood favorite since 1939 with an epic Sinatra jukebox.