Montego Bay Jamaica is Jamaica’s second-largest city and indisputably its tourist capital. The horseshoe-shaped Doctor’s Cave Beach, duty-free shopping, and year-round entertainment make it one of the Caribbean’s most popular resorts. If all you want to do is relax on the beach, snorkel in the azure waters of the bay, or sip cocktails by the sea, Montego Bay is the ideal place to do so.

Santiago, Cuba