The capital city of Puerto Rico and by some measures the oldest city in the United States, San Juan was established nearly five centuries ago by Spanish settlers. Old San Juan continues the tradition of the colonial town, where the historic fort of El Morro and mansion of La Fortaleza still stand.
The New World starts here: The first cathedral, university and hospital in the Americas opened in Santo Domingo, on the Dominican Republic's south-central coast. Numerous city sights pay tribute to the isle's rich history, including the Castle of Columbus and the museums of the Cultural Plaza.
Island heritage overflows in Jamaica, from the former seaside banana capital of Port Antonio to reggae legend Bob Marley's former Kingston home. Even natural attractions come with cool history: The age of stalagmite-filled Green Grotto Cave at Runaway Bay is estimated at 500,000 years.
Jacobean and Georgian buildings built from pink and white coral, Gothic churches and pirate castles with ornate ceilings dot the Barbados landscape. Two of the must-see buildings are stately St. Nicholas Abbey in St. Peter and the sugar plantation Drax Hall in St. George, both dating to the 1650s.
In the capital, St. John's, the baroque towers of an 1845 cathedral dominate the skyline; an 18th-century courthouse holds a museum of island artifacts. Antigua's historical district unfolds around English Harbour, the world's only Georgian dockyard, and Shirley Heights, a colonial observation post.