On the surface, Gibraltar appears to be little more than a boozy, sun kissed British overseas territory. Best known for its status as a tax haven, the tiny 2 square mile town consists of a myriad of crumbling housing estates and cobbled roads lined with shops hawking duty-free alcohol sprinkled in with a few British high street brands. However, few of us tourists make the trek down here for just the town. The towering Rock of Gibraltar is the territory’s main attraction and in addition to some of the best hiking I’ve ever experienced, it’s home to (in my opinion) a treasure trove of grossly underappreciated historic artifacts and features.
From a geographic perspective, Gibraltar sits at the southern tip of the European subcontinent and it is separated from Africa by the 9-mile wide Strait of Gibraltar. In antiquity, this was considered (more or less) the end of the known world. Providing access between the Mediterranean Sea and the Atlantic Ocean, Gibraltar has long been a sought after spot for both strategic military and trade reasons. Over millennia, a wide range of peoples and civilizations have made their mark on the rock. An avid fan of ancient history, I made it my mission to take a gander at some of its older sites starting from 40,000 BCE and ending in the 1400s.
St. Michael’s Cave
St. Michael’s Cave has a very unassuming tunnel entrance that opens up into a dazzling display of limestone stalactites and stalagmites carved by rainwater over countless years. This is the first significant cave I had ever visited and I was floored by how organic and beautiful it was. The cave has received several mentions throughout history and is also known to have provided shelter to Neolithic peoples (approx. 20,000 years ago) and Neanderthals (approx. 40,000 years ago) as evidenced by the skulls, cave painting and bowls that they left behind.
The Mediterranean Steps
Originally carved in the 18th century by the British as a means of traveling from one major defense point to another, the Mediterranean Steps scale nearly 200 meters of sheer limestone rock face. The steps make up a popular hiking path today and offer absolutely stunning views of the Mediterranean Sea and Spain’s Costa del Sol in the distance. It also passes by several structures and tunnels made by soldiers both in the 18th century and during WWII. The hike, however, is pretty challenging. While most tourist choose to climb up (from Jew’s Gate to O’hara’s Battery), it’s probably easier to take them down in the opposite direction.
The Pillars of Hercules
In classical antiquity, the Pillars of Hercules consisted of the Rock of Gibraltar and a neighboring peak across the strait in Africa (the exact peak is up for debate). At the crossroads between the Mediterranean Sea and the Atlantic Ocean, this was a crucial spot in the ancient world. It was mentioned by Plato and was settled by the Phoenicians, Romans, Carthaginians, and even the Vandals . Standing on Gibraltar’s peak and staring across the strait towards Africa put me through a bit of a time warp. As the geographic features have not really changed since ancient times, I could have easily been standing on the same spot and sharing the same view as an early Phoenician did settler 3,000 years ago.
The Moors conquered the Iberian Peninsula around 700 AD, which subsequently led to a centuries-long power struggle for Gibraltar. The origins of Gibraltar’s Moorish Castle date back to the 700s, but what stands today is a reconstruction from the Moors second time at Gibraltar’s helm in the 1400s. Today, there is unfortunately not a whole lot left to the structure, but it still provides a glimpse into the region’s rocky past.

Moorish Castle with Barbary Ape in the Foreground
















