Introduction

Old San Juan, Puerto Rico is an exciting prospect to cover in this edition of historical city tours. Old San Juan is the oldest continuously inhabited post-European contact city in the United States territory and the second oldest in the entire Western Hemisphere. If I’m being honest, I have no idea what that means but it’s definitely an old and historic city! 

Like many places across the Caribbean, Puerto Rico often found itself caught in the middle of greed and conflict between the major colonial powers. These influences appear prominent in San Juan’s architectural development. As you walk about the city you will notice buildings from different eras with different styles. Many of the buildings remain standing from the early 1500’s. But most noticeably, San Juan is home to multiple historical fortresses that protected the city from countless intruders. Follow along with this Sparked Travel guide as we highlight all the must see landmarks in San Juan, Puerto Rico

San Juan National Historic Site

If you’re short on time and only had to choose one site to see in San Juan then the San Juan National Historic Site is the one. The San Juan National Historic Site is one of the few places that is both a National Park and UNESCO World Heritage Site. This National Park location is home to the forts Castillo San Felipe del Morro and Castillo San Cristóbal along with a multitude of other historical buildings making up these massive fortifications. The two main fortresses are connected by a short one mile trail that stretches along the North Atlantic Ocean making it a scenic stroll.

Castillo San Cristóbal is the first stop on our tour and actually the younger of the two San Juan forts. NPS states the Spanish began building the fort after devastating attacks from both english and dutch forces. The fortress was built to protect the city of San Juan from any land attacks from the east. After 150 years, Castillo San Cristóbal was finally complete and is considered one of the largest fortresses in the Americas. The architects of this compound pulled out all of the stops to make this one of the most secure points on the island. San Cristóbal boasts three levels, a series of outer defenses, a complex tunnel system, and more defense mechanisms to strike fear into any invader. Exploring these grounds of this great military complex will surely transport any traveler back through time.

As you walk west, the looming citadel, Castillo San Felipe del Morro (El Morro for short) will begin to take shape, valiantly perched on the island’s outlet. El Morro was Old San Juan’s sea protector and a successful one as it is still standing today. This six level fortress is complete with barracks, dungeons, tunnels, walls, and even some authentic cannons. It’s very clear just how crucial Puerto Rico was for the Spanish conquests. Just be sure to make it to the lookout at the very end of the fortress as it overlooks the ocean and is the perfect spot to take some iconic photos. If you want an in depth history of these landmarks check out the discover Puerto Rico website here where they have free guided walking tour audio on Spotify! It’s also important to mention that El Morro closes at 4:30! Don’t make the same mistake I made and arrive at 4:00 leaving no time to explore the fortress. If you do make the same mistake, travelers can walk the Paseo del Morro Scenic Trail for free! It leads you all around the fortress, down by the crashing waves, and then back into the city right near La Fortaleza.  

San Juan Cathedral

It can hardly be considered a walking tour if you don’t stop at one of the city’s cathedrals, right? Typically cathedrals are one of the first things built in an establishment and often carry much weight within the community making it a centerpiece for learning the history. Not far from El Morro, travelers will find the Catedral de San Juan Batista which happens to be one of the oldest buildings in San Juan and the second oldest cathedral in the Western Hemisphere! This pristine looking building is a testament to the strength and will of Puerto Rico. Whether it be invaders or severe weather, the San Juan Cathedral has been through it all. The cathedral may have suffered damage along the way but the people of San Juan have always banded together to build back the cathedral stronger than before. If you want a great view of the Cathedral and the skyline as the sun sets, checkout Bar Catedral Rooftop. We enjoyed a nice cocktail here before heading back to our hotel

La Fortaleza

As you continue on through the cobbled streets of Old San Juan you will happen upon the pale blue Government building La Fortaleza. Its title translated to English means the fortress which is quite an interesting name for the Governor’s residence but when you look at its history it has taken on many faces over the years. Originally and to no surprise, La Fortaleza served as a separate fortress for San Juan but after falling to one of the invasions the island’s leadership decided to repurpose the building. 

Today, the building has housed well over a hundred governors of Puerto Rico. Walking the grounds of La Fortaleza is unfortunately not allowed unless you book a guided tour by calling ahead or on site. The building is well hidden behind guards and walls but just nearby, travelers can walk the trendy Fortaleza Street. There is often an art installation above this street. It can vary but there have been colorful umbrellas, kites, and even the Puerto Rican flag floating above the street. Perfect for an Instagram story. 

Old San Juan is by no means a large city and is quite walkable making exploration of this historic place easy. Travelers can turn down different corners and be in awe at the unique and colorful buildings. Some more landmarks that travelers should consider while in Old San Juan include Paseo de La Princesa which is San Juans lovely scenic walkway, Plaza de Armas which is a gorgeous and historic plaza, and Cuartel de Ballajá which are former military barracks. Aside from these landmarks, the area offers no shortage of food and fun with many restaurants and bars beckoning travelers from their full day of walking. If I missed any must see sites in Old San Juan be sure to connect by leaving your comments below!