Montego Bay, Montego Bay
Concierge.com's insider take:
Columbus called it El Golfo di Buen Tiempo, "The Bay of Good Weather," but it wasn't until 1906 that northerners started to take advantage of Montego Bay's white sand and mineral-spring waters. Today, it's Jamaica's second-largest city, with a main road known as the "Hip Strip" for all its cafés, bars, and restaurants, and reggae blaring from every doorway. When visitors can drag themselves away from town and Doctor's Cave Beach, they go river rafting and river tubing, souvenir shopping at Old Fort Craft Market on the corner of Fort Street and Howard Cooke Boulevard, or walking underwater, among the parrot fish and angelfish of the 24-square-mile Montego Bay Marine Park off Pier 1, with the help of lightweight diver's helmets.