Gloucester Avenue, universally called the Hip Strip, is the spine of touristic Montego Bay — about a mile and a half of beachside hotels, bars, jerk shacks, dive shops, craft stalls, duty-free electronics shops, and the entrances to the three main beaches (Doctor's Cave, Cornwall, and the public Walter Fletcher / Aquasol). It is exactly what it sounds like: a self-contained tourist bubble where you can spend a week without ever encountering the real city.
That said, it does its job well. The beach access is good, the restaurants range from the touristy (Margaritaville) to the genuinely decent (Marguerite's, the Pelican Grill), the bars stay open late, and the strip is reasonably safe to walk at night. For a glimpse of the city beyond the tourist zone, walk twenty minutes south along Sunset Boulevard into Sam Sharpe Square and downtown.