The oldest colonial city of the Americas and a UNESCO Heritage Site, Santo Domingo deserves to be on every history lover’s agenda. The capital of the Dominican Republic boasts of the first street, first military fortress and first cathedral of the Spanish-settled New World. Go see.

Jamaica’s labyrinth of caves running 1,525 meters in length and 12 meters in depth, is not just a natural wonder. Spaniards hideout during English invasion, arms smuggling route to Cuba, haven for runaway slaves, storage place for rum barrels during the Second World War…Green Grotto has serious history to offer. Surprise yourself.

Ruin lover? Consider a trip to the old Mayan city of Chichen Itza. Take a tour if you want to hear stories. Settle for a freewheeling exploration if history is not your game. Massive step pyramid, graphic stone carvings and a nightly sound-and-light show for the fact-finder in you.

A 2.5-mile path takes you along a tour of 16 iconic landmarks, including Paul Revere's house, Old North Church, Bunker Hill and USS Constitution. Solid American history, every step of the way, with just a local app to guide you. Grab a bite at the Union Oyster House, one of Boston’s oldest restaurants.

History fans, make a beeline for Cartago. The old capital of the country during the Spanish rule has some great sites, including the ruins of Santiago Apóstol Parish. Craving Mayan templesque…this it is.