Known locally as the Hip Strip, Jimmy Cliff Boulevard (formerly Gloucester Avenue) is a lively, mile‑long waterfront stretch full of brightly painted restaurants, reggae music, rum cocktails, and souvenir shops—perfect for an evening out. Expect casual bars and clubs, street food stalls serving smoked jerk chicken, and small craft vendors. At the southern end are the remnants of Fort Montego and a craft market; at the northern tip is Dead End Beach, a popular spot to watch planes land at nearby Sangster International Airport.