From birdies to bogeys, you'll find love on the links in Stamford. Of all the cities on our list, it has the most golf courses nearby. Back at the clubhouse, score a spot on a sloop for a sail around Long Island Sound. Stamford has three yacht clubs to choose from, and they love to race.
For music lovers, the city has its own symphony and the Stamford Center for the Arts, which features local and touring acts. After a show, hunt for a hedge fund manager at one of the bars or restaurants around downtown's Columbus Park.