This chapel on a cliff is renowned for its healing powers and was founded on the site of a supposed divine intervention.

This colorful gate stands as an entrance to the walled city of Old San Juan.

The first official clock in North America, it kept time for the Spanish government of Santo Domingo.

After Christopher Columbus died, his son built a fancy house to rule from.

The first hospital in the New World.

The oldest colonial fortress in the Americas was once the home and later prison of Christopher Columbus.

Built in 1512, the oldest cathedral in the Americas.

The capital of the Cayman Islands is a center of offshore banking, but gets battered by blistering hurricanes.

A tomb in this cemetery holds soil from every country in Latin America.

An old slave lookout in Cuba's historic sugar cane fields.

This imposing memorial contains the remains of Che Guevara — and 29 other guerrillas who died with him in Bolivia.

Four antique Baldwin trains are kept on display in the Mal Tiempo train depot.

A colossal statue with a controversial past, forgotten for more than 30 years.

After the Cuban Revolution, the famous rum company had to leave their swanky headquarters behind.

Once a favorite playground for the world's most illustrious guests, Hotel Nacional's secret weapons and bunkers reveal a more menacing side to its golden history.

Castro's communist ice cream mothership has been serving five-scoop "salads" for over 50 years.

A focal point of the Cuban government, this city square features one of the most iconic images in the country.

In terms of history and architecture, this is one of the most remarkable cemeteries in the world.

Prehistoric history as seen through the lens of an outsider artist.

Neo-cave art on the macro scale.

Dating back to the second century, vestiges of prehispanic mural paintings are found in this underground palace.

The unique collection often goes unnoticed by visitors focused only on the archaeological objects.

Abandoned figurines adorn a small plot on the side of a craft market's entrance.

A museum in the former home of Marxist revolutionary Leon Trotsky.