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Old San Juan
by Jim McGee

The image most associated with San Juan is of a cupola suspended from the walls of El Morro, the fort that protected San Juan from invaders during colonial times. You’ll find it on post cards, posters, even on license plates. So as photographers we feel obligated to capture some images of the fort. But while El Morro certainly dominates the entrance to San Juan Harbor, the city of Old San Juan is a picturesque gem that is wonderful to experience, offering the traveling photographer a wealth of friendly people, great food, memorable images, and a rich history that makes your subjects all the more interesting. 

Old vs. New San Juan
There are two distinct San Juans. New San Juan is a sprawling modern city. Old San Juan sits on a small peninsula that encloses San Juan harbor. This was the original San Juan. A 500 year old city. 

Puerto Rico was discovered by Christopher Columbus and claimed for Spain on his second voyage to the new world in 1493 and the first colony was established here in 1508. At that time the Spanish, English, and Dutch had all amassed fortunes built on colonial empires and desirable colonies were taken from rival countries by force. In 1625 the Dutch burned San Juan to the ground, including the churches and the bishop’s library – at the time the most famous and complete collection of books in America. 

Strong defenses meant survival. El Morro was built over a period of 241 years. It dominates the entrance to San Juan harbor and its walls extend out to enclose Old San Juan. It is huge and imposing even today. As you stand at the entrance to the fort it is hard to imagine the sheer will that it would have taken to assault this fortress, crossing its dry moat and attempting to scale its walls with ladders; all while under fire from above. Yet El Morro was attacked numerous times, and conquered once while still in the early stages of construction. Walk up the steep ramps inside its walls and you can easily imagine the fierce hand-to-hand battles that once raged inside these walls. 

But walk out of the fort today and you leave thoughts of blood and battle behind. On the manicured lawn under a tropical sun school children are flying kites, people are setting up picnic lunches, and it’s a short pleasant walk into the heart of old San Juan. 

Walking the City
Walking is the best way to get around Old San Juan and you can easily walk all of the old city. Parts of the city wall were demolished over the years to make way for new construction and only one of the original city gates remain today, the Puerta de San Juan (San Juan Gate).

This was the entrance into the city from the harbor and from the gate a steep cobbled street leads upward to a  Cathedral. When a ship arrived, the first thing passengers and crew did was to walk up to the Cathedral and give thanks for a safe voyage. Remember that the city was built before accurate charts or modern navigational aids for sailors existed. Those who arrived in San Juan had navigated uncharted reefs, survived fierce storms at sea, disease, and had eluded both pirates and enemy warships. So those that made the journey safely had ample reason to give thanks. 

Walk through the gate today, stroll to your right and you’ll find yourself in the heart of Old San Juan’s shopping district. Tightly packed together are a variety of jewelry stores, antique shops, art galleries, tourist traps, and restaurants. 

If you can’t find a good meal in Old San Juan shame on you! Puerto Rican food is rich and flavorful but not at all spicy like Mexican food. And don’t be afraid to try new things such as fried sweet plantains (a type of banana) or any of a number of main dishes such as arroz con pollo (rice simmered in coconut milk and served with chicken). Toast a hearty meal with a pinã colada or any of a number of rum drinks made with local rum (Bacardi is across the bay in Cataño). There’s almost always a breeze coming in off the ocean and on a warm night it’s hard to imagine anything more pleasant than a meal at one of San Juan’s sidewalk cafes. 

While prowling the restaurants and shops take a look in the back. At one time these were residences that predated air conditioning by several centuries. Windows opened onto small courtyards that acted as breezeways to promote air circulation. Some of these courtyards and their accompanying fountains are brightly painted or decorated with tiles and make great photo subjects. 

If you’re not in the mood for a “sit down” restaurant (or you don’t want to spend the money because you’re saving up for a new lens) try the food vendors in the Plaza de la Marina or along the promenade Paseo del la Princesa that connects the plaza to the harbor. Vendors sell fresh, non-alcoholic, pinã coladas made from coconut milk and pineapple juice, roasted kebabs, fresh fruit, and several varieties of tasty fried meat pies. 

On weekend afternoons and in the early evening you’ll see numerous games of dominoes being played. Animated and convivial social gatherings as well as games, the players make great photo subjects – just make sure to ask permission before intruding.   

On weekends you’ll also find numerous outdoor vendors selling their wares along the Paseo del la Princesa and in the Plaza San José. You’ll find a variety of items ranging from junk to wood carvings, folk art, religious items, ceramics, and jewelry. 

During a hot afternoon make sure you stop and sample the heyados that are sold on street corners throughout the city. Heyados are creamy, flavored ices available in coconut, pinã colada, and local juice flavors. Sold for a dollar they are a sweet and refreshing way to take the edge off the heat. 

San Juan has taken great pains in recent years to ensure that improvements to buildings are consistent with the architecture of the district. But that architecture is itself an eclectic mix of styles that range from Moorish to Art Deco. Bright colors and balconies are the norm throughout the district, as are decorative plants and flowers. All conspire together to make the streets of Old San Juan incredibly picturesque. Don’t limit yourself to just the main streets that bisect Old San Juan. Stroll up its steep side streets and alleys where you’ll find a variety of interesting houses, shops, and the odd restaurant and bar.    

You may also see an unexpected slice of life in these residential neighborhoods away from the tourist areas. While kneeling down to shoot some statuary I suddenly heard a man shouting repeatedly up at an apartment building in Spanish. As I watched an old woman walked out onto one of the balconies and started shouting back down at him. The shouts sounded friendly and as I watched she picked up a rope, tied it off to the railing and lowered a basket down to the man. He filled the basket with groceries which she pulled up to her apartment. Delivery San Juan style! 

After hauling the basket in she exchanged good natured shouts with the man then turned at waved at me. Seems she'd seen me taking her picture.  

You’ll notice that even the cobblestones have color in Old San Juan. Rather than being cut from stone or cast as bricks these cobblestones were an ingenious use of slag from Spain’s iron foundries. Slag is the waste when iron is refined and was usually piled in huge slagheaps at foundries. But cast into blocks the slag made terrific long lasting cobblestones. The stones were brought to the island as ballast in ships in the 16th century and their blue tint gives the streets a colorful look. 

In the shops or if you’re lucky enough to be in town during a carnival you’ll see caretas – paper mâché masks worn by costumed revelers (vejigantes) during carnivals. I heard several conflicting stories about the history of these masks claiming the origins to be from Spain, the native Taíno Indians, or from Africans brought to Puerto Rico as slaves. No matter the original source their brightly colored, horned, grotesque visages make great targets for your lens. 

For beaches head just out of Old San Juan to Isla Verde and the Condado; both of which lie between Old and New San Juan. There you can find beach hotels and a hammock under a palm tree where you can relax your tired legs. But once you’ve rested up head back into Old San Juan. On Friday and Saturday nights the city’s bars and clubs rock! 

Getting Around
Most hotels are not walking distance from Old San Juan so the best way to get there is by cab. Once within the city walls you can walk anywhere. If you have a car park in one of several garages, they’re cheap compared to what you’d pay in most U.S. cities and street parking can be difficult to find. 

Normally I don’t give advice on how you should get around. The assumption is that you’ll just rent a car when you get there. But in Puerto Rico I’d say only rent a car if you have to and if you think nothing of driving among the insane. Driving in Puerto Rico makes New York or LA feel like a relaxing drive in the country. 

In the seven days I was on the island I witnessed 10 or 12 serious wrecks. Puerto Rico is one of the most densely populated places in the hemisphere. Many drivers here attack the road with reckless abandon and traffic laws are treated as mere suggestions. It’s not unusual to come up behind a car doing 35mph in the left lane of a four-lane highway or to be passed on the shoulder (or in one case on the sidewalk) by cars running at breakneck speeds through heavy traffic. I regularly drive in New York yet found driving habits in Puerto Rico to be surprising. The roads themselves are often pot holed or badly repaired. This is especially true when driving outside the city; you need to be on the lookout for potholes, other drivers and the occasional goat or chicken in the road. 

In the mountains roads are narrow and drivers often drift into your lane on turns. It’s also not unusual to see part of the road washed out or to see mud and rock slides partially blocking your way. I didn’t see many speed limit signs so your best bet is to pace yourself with the local traffic. 

On the plus side getting in and out of Puerto Rico is easy for Americans. There is no customs to clear and the coin of the realm is the U.S. dollar. There has been some debate in recent years over language. Officially both English and Spanish are the languages of Puerto Rico. Unofficially Puerto Rico is definitely Spanish speaking – though you’ll find most folks can speak some English and many move from one language to the other with an enviable ease. It still doesn’t hurt to know a few basic phrases in Spanish, especially if you’ll be traveling outside the tourist areas. I always find it’s more polite to ask first in Spanish if someone speaks English rather than just assuming that they do. 

Final Thoughts
Old San Juan is beautiful and the people I met there were universally friendly. Throw in a tropical sunset and it’s hard to imagine a more inviting travel/photo destination.


You may have heard stories about crime in San Juan. If you spend your time in Old San Juan and in the hotel district along the Condado you shouldn’t have any problems. Police are visible all over these areas. The one exception is the La Perla section. Outside the city walls just east of El Morro, La Perla is a mix of brightly colored houses and shacks piled one atop the other. La Perla might look inviting to a tourist or a photographer but venturing into this neighborhood is an invitation to trouble. With it’s vibrant colors set against the Atlantic Ocean one cab driver referred to La Perla as the islands “best looking slum”. He indicated that he wouldn’t even consider taking a tourist into La Perla. Advice you should heed. 



Special thanks to Wilfredo Ramirz,
our guide in Old San Juan

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