Puerto Rico’s long and vibrant history can be intimidating to the uninitiated. Luckily, everywhere you turn here, there are relics, ruins, and historic buildings to really spell out the Island’s many stirring chapters. 

Take the 400-year-old Puerta de San Juan, for example. It’s the oldest standing gateway into the even older city of Old San Juan—celebrating its 500th anniversary this year, in fact—which once functioned to fend off pirate attacks. Of course, there’s plenty of history beyond the capital city, as well.

There’s a museum that pays tribute to Indigenous Taíno communities in Jayuya; a beachy set of ruins in Quebradillas rumored to have served as a pirate hide-out; remnants of the first Spanish settlement in Guaynabo; an unassuming 19th-century bridge that played an important role in the Spanish-American War; and much, much more. 

The number of historical sites to visit in Puerto Rico is immense, but this list presents a century-spanning cross-section of its past that is a helpful introduction to this one-of-a-kind Island.