Old San Juan: Explore a Gorgeous Walled City in Puerto Rico

When most people are asked to name the oldest city in the United States, they say St. Augustine, Florida—which was founded in 1565. The gorgeous island of Puerto Rico—which has been a United States territory since 1917—is home to a walled city called Old San Juan which was settled in 1521. Old San Juan is home to striking architecture, a stately ceramic totem pole, and a lively dive bar that has long attracted rock ‘n roll royalty. Visitors can soak up Old San Juan’s rich history and enjoy a sweeping view of the sapphire waters of the Caribbean by crossing a bridge that connects Old San Juan with the rest of Puerto Rico.

There aren’t many walled cities left in the Western Hemisphere. La Puerta de San Juan is a stately red door that was constructed in 1635 that allows travelers to enter the once-heavily fortified city. Today, visitors can stroll through La Puerta de San Juan to make a grand entrance into the peaceful and picturesque city of Old San Juan.

One of Old San Juan’s most striking attractions is the Plaza del Totem—a public square that features a towering ceramic totem pole known as Totem Telurico that was created by artist Jaime Suarez. The totem pole features pieces of shattered pottery that jut out from a cylindrical totem pole like the spikes of a stegosaurus. The shattered pottery represents the at times chaotic relationship between European settlers and Indigenous people of the Americas. Plaza del Totem also features two obelisks that point towards the north star—in honor of the European adventurers who crossed the sea to explore the New World.

Old San Juan is also known for its lively bar and restaurant scene. A rustic dive bar known as El Batey has been offering costumers a loud, gritty place to sip on a beer or cocktail since the early 1960s. Counter culture luminaries such as beat poet Allen Ginsberg, writer and journalist Hunter S. Thompson, and Rolling Stones guitarist Keith Richards often frequented El Batey when the bar first opened. Today, you can pull up a bar stool at El Batey and listen to the timeless music of Pink Floyd as you attempt to decipher the graffiti on the walls that has accumulated over 6 decades.

Old San Juan is an elegant, historic city that is the ideal place to relax, soak up some history. and have a seat a historic bar.

Explorer Passport

Next badge: Trail Scout

Unlocked after exploring 5 different unusual places.

0 of 5 places explored