San Felipe de Barajas Castle

Cartagena’s strategic significance as Europe’s conquest of the Americas intensified cannot be overstated. Some say that if the British had won the 1741 Battle of Cartagena, that South America would now speak English. They didn’t, largely because of massive El Castillo San Felipe de Barajas, the largest and most formidable Spanish colonial fortress in the hemisphere.

Begun in 1536, almost immediately after the conquistadors arrived, the massive megastructure sits atop San Lazaro Hill, with flawless views across the harbor. Bristling with cannons and other armaments, it was enlarged and re-fortified in 1657 and 1763 as part of an ongoing arms race against other European powers. A marvel of military engineering, the compound’s angles and parapets offer maximum coverage, and are connected by a warren of secret tunnels threading the mountain of stone.  

It’s worth hiring a guide to explain the significance of the structure, though the beautiful views from the gracefully aging old turrets are stunning in and of themselves. Come close to sunset, when trumpet players take advantage of the crumbling structure’s acoustics.

Just outside the fortress is the Old Shoe Monument, a popular photo op that commemorates a poem by Cartagena wordsmith Luis Carlos Lopez, who famously compared the old city to a worn, but comfortable, pair of shoes.