Walking the Streets of Old San Juan
Stepping out into the fresh air, there is a lovely scene unfolding in the oldest plaza in San Juan in front of the oldest cathedral in the Americas. A woman in a dress stretches as a man photographs the indolent afternoon.
It is sunny and bright as I continue my walk and every turn I make has me swooning like candy for my senses.
Each cobblestoned street breathes into my imagination ladies with parasols and colonial-style gowns, gentlemen in top hats and canes, monks in coarse cloth clutching symbols of their god, swarthy seafarers, hardy women hanging laundry in the strong sun, young boys selling newspapers, and stray dogs running about the drains all mixing together in the salty Caribbean air.
A century or more ago, during times of political intrigue and tumult, an identity was forged by mighty cannons around Old San Juan gate protecting the city from the constant and revolving clash of countries hell-bent on colonizing the world. The French, Spanish, English, and Dutch all fought for control of this port city.
I feel all that energy and passion as I walk the streets of this hilly city. I can practically hear the iron clatter and busy clang of carriages and markets.
These days though, it’s much less salty and much more sweet.
Villa Herencia
On our third day in San Juan, Katie and I left the younger neighborhood of Condado to arrive in Viejo San Juan (aka Old San Juan).
Our Uber dropped us off at Villa Herencia, an 8-bedroom guest house just a block away from San Juan Bautista, the oldest cathedral in North America and the second oldest in the Western Hemisphere.
The Old World European aesthetic present on the streets is also in this guesthouse. Patina walls, high ceilings, dark wood, and ornate décor define the look.
Walking in, there is a dim and narrow vestibule that leads into an open-air courtyard. It’s beautifully tiled and a tree grows up into the sky while other manners of curated botany dot the periphery. Where the tree’s roots grow, the tile is lumpy and breaking, which adds immensely to the charming aesthetic.
A staircase loops from the courtyard onto a lush rooftop terrace draped in flowers and vines. At the edge of the roof, a railing overlooks the cobblestoned streets and one feels transported back to a time when kids left home to seek their fortune with just a bindle and their wits.
That night, the fountain running in the courtyard lulls us to sleep and we sleep well into the late morning in our fabulously dark and cozy room with a massive, firm mattress.
The Cats of Old San Juan
An adorable detail of Old San Juan are the numerous cats who roam the streets like it’s a well-kept backyard of theirs.
They are clean and sweet and trusting. Little plates of water and food are laid out for them and they sleep under park benches, curled into sweet puddles in the tall grass.
Are they wild or merely outdoor domestics? Perhaps a combination of both. Maybe it accounts for the remarkably clean streets here.
Sunset at Castillo San Felipe del Morro
Once settled in, we walk to Castillo San Felipe del Morro, a 16th century Spanish fort, to catch the sunset.
The Spanish built many of these forts in Puerto Rico to protect the land from invaders.
Surrounding the fort are cascades of soft green grass that stretch for miles. The Spanish military used to practice drills on this yard. Today, little splashes of people dot the epic landscape. The colors of the setting sun, the indomitable fort, and the water create a lovely scene.
Katie made friends with a nearby kitty looking for scritches and scratches.
Unfortunately, the fort is closed due to COVID but it was still fun to walk up to the massive doors and knock on the burly wood.
El Jabirito
We go to El Jabirito for dinner. It was recommended to us by our Uber driver. The lobby is small and cramped, but the place seems legit with a mixture of locals and tourists.
There’s a giant fish tank in the back of the restaurant and cute replicas of the European-style balconies of Old San Juan hanging on the walls.
I order the steak with red sauce and rice/beans. Katie gets the shrimp mofongo. The red sauce is like a gravy and has some red peppers in it. The steak is tender and tasty, and when everything is mixed together with rice and beans? Mmm mm!
What we order has been the typical local cuisine: a protein (usually steak, chicken, or shrimp) accompanied by a carb (rice and beans or mofongo). And, to be honest, while I have enjoyed the local food, I haven’t been blown away. To be fair, maybe I am not ordering correctly; it would help to have a local be my food guide. Any suggestions?
Cuartel del Bellaja Barracks and the Don Ruiz Coffee Shop
The next morning, eager to get my caffeine fix, I hoofed it to Don Ruiz coffee shop located in the historic Cuartel del Bellaja Barracks.
The facility was completed in 1864 to house up to 1,000 Spanish soldiers and their families, as well as “storage rooms, kitchens, mess halls, dungeons, and horse stables.”
In response, my vivid imagination conjures up secret tunnels and political prisoners, masked Zorro’s and Count of Monte Cristo’s locked up in underground dungeons, torches lighting up dank passageways dripping with the earth’s condensation.
As you can probably tell, the Victorian era holds a lot of intrigue for me. Repressed people and yet everybody was on opium, the opulence, the exploration, the meeting of many different cultures for the first time in modern-ish history, and the last vestiges of the old before the world was to be rocked by the modern developments of the 20th century.
Today, in the bright light of a Friday afternoon in the year 2020, this picture is nary the reality.
On the outside, the building is a bright and cheerful rusty orange with clean, white trim. Inside is a vast and open patio, massive and empty except for a couple of tables and chairs.
The café is small and the barista friendly. He tells me the barracks were converted to a military hospital after America won the Spanish-American War. These days, it is used for office space, art studios, and a museum.
San Juan Bautista Cathedral
San Juan Bautista is listed as one of the must-sees in Viejo San Juan. “The oldest cathedral in North America and the second oldest cathedral in the Americas,” all the blogs say.
Ponce de Leon is interned at San Juan Bautista cathedral. I wondered if I should even step foot in the cathedral, it felt so wrong and icky.
While governor of San Juan and Puerto Rico, he enslaved the local people, the Taino, and distributed them among Spanish settlers. The land where they had been living for years was divvied up as well and they were made to work the land as slaves. The rulers were cruel and decimated the Taino using methods of control that were beyond inhuman.
The brutality was so much in fact, that one of these men, Bartolome de las Casas renounced and became a priest, spending the rest of his life in service to humanitarian efforts. He wrote extensively of the cruelty he witnessed. Reading about the history of Spanish rule in Puerto Rico makes me sick. It is horrific.
And yet, according to one researcher, 30% of modern-day Puerto Ricans are descended from Ponce de Leon and his wife. That’s one hell of a history to reconcile.
When I arrive at the cathedral, it is a Friday afternoon and there are only a handful of people in the pews listening to the priest’s voice bellowing in the cavernous church. Being in the space brings me back to my childhood going to church and listening to a male voice echoing religiosity.
Quietly, I roam the outskirts, feeling a heavy weight in this ritualistic space.
There is something daunting about it. Something overwhelming. Like a heavy secret. So much death, condemnation, and persecution occurs in the name of religion and ideology.
I look for signs of Ponce de Leon amongst the the usual symbols and sacred spaces, candles and talismans, incense and effigies.
What is it about cathedrals that feels like the air has been locked up for centuries? It’s like walking into a force field. I leave before things get weird.
Gallery Inn
The next night, we stay at the acclaimed Gallery Inn. As I step into a courtyard with sculptures, gardens, and the sound of running water dripping from a fountain, I spy a scarlet Macaw looking askance at me through one eye. Next to her is a large blue bird in a cage hanging upside down, looking pretty silly.
This beautiful and decadent hotel is made up of six adjoining buildings dating back to the mid-18th century, combined into one large mansion-style inn.
The pool is not just any pool but one that’s built amidst ruins of the original walls and surrounded with art. Plants flourish in every nook of the hotel. The décor is baroque and elegant, just like at Villa Herencia but on another level.
The setting is from a Spanish colonial villa in the Victorian era: heavy books, brocade and velvet fabrics, ornately carved furniture made of dark, heavy wood, melodramatic sculptures, Grecian busts, framed portraits, patterned wallpaper, Oriental rugs, heavy curtains, little knick-knacks from faraway places, and deep jewel tones of emerald greens, ruby reds, and rich gold transport one back to a more elegant and decadent time of Spanish colonialism.
Towards the back of the building is the parlor (my favorite room). Here, natural sunlight streams in from a balcony overlooking Calle San Sebastian. Tucked against the wall in front of an ornate floor-to-ceiling mirror is a piano and a scarlet, velvet couch with matching armchairs, the perfect place to sip one’s morning coffee, while feeling like a princess.
We’re staying in the Vista room, which has a balcony overlooking the Atlantic. It’s furnished with a very comfortable king-sized canopy bed and decorated in the same baroque elegance as the rest of the hotel.
That night, there is a piano concerto in the pool and lounge area. Unfortunately I have to take a conference call, but Katie was able to attend and I got to hang with everybody afterwards.
La Perla
Within view of our balcony is a neighborhood of colorful homes outside the Old San Juan gate and along the rocky coastline. They are built in the colorful style of so many Caribbean homes and catch the eye. Welcome to La Perla, a historic shantytown; also where the music video for “Despacito” was filmed.
According to Wikipedia, “La Perla was established in the late 19th century. Initially, the area was the site of a slaughterhouse because the law required them and homes of former slaves and homeless non-white servants — as well as cemeteries — to be established away from the main community center; in this case, outside the city walls. Sometime after, some of the farmers and workers started living around the slaughterhouse and shortly established their houses there.”
Since the filming of Despacito, some plucky tourists have made their way to La Perla, this town on the fringes of Old San Juan society. I was terribly intrigued as well. There was also an Airbnb in La Perla that we happened upon.
A few days later, however, I happened to chat with a local cop who cautioned me against even visiting.
“Lots of drugs … and when the sun goes down, it changes …” he said, warning me of the zig-zagged streets and alleyways.
The Old San Juan Cemetary
Next to La Perla is the Cementerio Santa María Magdalena de Pazzi where many famous Puerto Ricans are buried, including Pedro Albizu Campos, a hero.
He led the fight for Puerto Rico’s independence and was punished heavily for his convictions. Go read his Wikipedia page if you don’t know who he is, it will give you the chills. One hell of a man.
The cemetery overlooks the Atlantic Ocean and the tombstones sparkle a pure white in the sunshine. It’s a nice place to appreciate the view and chat with the other people putzing around.
A Proper San Juan Apartment
Walking to the other fort, Castillo de San Cristobal, just a short walk from San Felipe del Morro, we stop by a new friend’s rental townhouse.
Our two new friends we met quite serendipitously and synchronously. We ran into them outside our hotel; one of them had taken kitesurfing lessons with Katie the day before. He had recently moved to Viejo San Juan, escaping the craziness of the West Coast, USA. The other, was his friend visiting from the states.
The interior of his newly rented townhouse was two richly-decorated floors of beautiful art from around the world inside a quirky and beautiful space. The details I appreciated were:
- a liquor cabinet from Japan
- heavy kimono (I think?) hanging on the walls
- gallery of butterflies pinned behind glass
- beautiful furniture
- high ceilings
- spiral staircase
- and, of course, a balcony opening out onto the street.
What a special experience to explore an Old San Juan apartment.
Plaza Darsenas and Paseo de la Princesa
Passing Castillo de San Cristobal, which is also closed, we turn onto Avenida Luis Munoz Rivera and head to Plaza Darsenas.
According to TripAdvisor, it’s usually a lively spot in town for food trucks, people watching, and live music.
During these COVID times, there are some vendors selling agua refrescas and virgin pina coladas, but otherwise not much activity.
We continue on to Paseo de la Princesa, a pretty walkway that would also usually have many vendors but not today.
Instead, it is us and some other people walking around as golden hour dawns, creating magical lighting. Ahead of us, the Raices Fountain is lit with a soft ambient glow.
The fountain was built between 1991 to 1992 and is chock full of symbolism about Puerto Rican culture and history.
Café El Punto
For dinner, we head to Café El Punto located on Calle de la Fortaleza
Upon entering, one is immediately met by very formidable, devilish, horned masks that leer at you from behind painted eyes. Ignorant as to what they were, I was highly unsettled by these demonic faces following my every move.
I later learned this is a part of Puerto Rican culture. These scary faces are in fact vejigante — a Christmas figure in Puerto Rican folklore that is a combination of Spanish, African, and Caribbean influence. Around the holidays, the vejigante, the trickster, goes around lashing people to beat away any evil spirits.
Anyway, back to the food. As a starter, we order the conch salad. It’s my first time trying conch and while it kind of looks like a mussel, texturally it’s like a piece of chewy octopus.
For my entrée, I order the stuffed avocado with shrimp and rice and beans. It’s good, a solid meal. The shrimp dishes in Puerto Rico are always on point.
The Casablanca Hotel
Our last night, we stay at the Casablanca Hotel. Its location on Calle de la Fortaleza is tourist central with numerous souvenir shops full of kitschy knick-knacks that apparently somebody somewhere always buys.
Where the Gallery Inn transports you back in time, Casablanca Hotel brings you back into the 21st century with a nod to the past.
Modern aesthetics of bold, vibrant colors like hot pink and sky blue meet baroque traditions and patterns.
Our room is clean and the bed big and comfortable. Instead of a pool there are large stone bathtubs on the roof. And soon after settling in, we run a bath under the clouds with an epic view of the city, including Castillo de San Cristobal.
Café Manolin
Near Casablanca Hotel is Café Manolin, a local diner serving criollo food for over 70 years.
I order the churrasco and Katie gets the mofongo with chicken and red sauce.
The chicken mofongo with red sauce is f*cking delicious! Now, I am inspired to order mofongo on my own because I am pretty sure I’ve tasted mofongo done right.
On the flip side, DO NOT order the churrasco.
Calle de la Fortaleza
My last morning in Old San Juan, I embark on my very own walking tour of the city. Since the streets are arranged in a grid, I decided to walk up and down each street, starting at Calle de la Fortaleza.
At the very end of this street, in front of the governor’s mansion, is a well known attraction that’s also called Umbrella Street. These days, the umbrellas have been replaced with a big flag of Puerto Rico.
When I arrive, the block is barricaded and guarded by some police officers. This is a temporary blockade due to recent elections.
My curiosity about local politics stirred, I chat with one of the cops about the history and politics of Puerto Rico. He is very friendly and proud of Puerto Rico.
He tells me about the origin of the flag being potentially from the freemasons, the multiple party political system, and the friendliness of Puerto Rican people before he has to go back to work. One of the other officers is a great Instagram boyfriend and takes a fantastic photo for me.
Puerta de San Juan
Soon, it begins to drizzle but undeterred, I continue my walk around the city.
One of my stops is Puerta de San Juan, one of the original five gates to the city. Each of the gates had a delegated purpose and this one was reserved for special occasions, like visits by dignitaries.
It served this special purpose because it was minutes away from San Juan Bautista Cathedral so visitors could visit holy ground ASAP upon arrival and give kudos to their homeboy for safe travels.
Each night, the gates were closed and sealed, so if you didn’t come back in time, you were out of luck until the morning.
Plaza de Armas
Another landmark to check out is the Plaza de Armas.
It’s a good place to people watch. There’s a small coffee stand at one corner next to a pergola where I watched an artsy guy paint on a pad with a small slate of watercolors.
On the other end of the plaza is a fountain where many pigeons congregate. People throw food for them and take pictures, which I’ve never understood and probably never will.
If pigeons appeal to you, however, there’s also Parque Las Palomas (literally “Pigeon Park”) over by Paseo de la Princesa.
Poet’s Passage
From the plaza, I spy an interesting façade of a store called Poet’s Passage. The owners are a husband and wife, artist and poet duo and they make their own items.
For sale are uplifting poetic sayings written on various home goods like magnets and mugs. I think there were poetry slams and readings before COVID hit.
Her husband has his own craft, painting scenes from the city, as well as miniature doors of Old San Juan, it’s a special niche and one that’s unique to the place. Between the two of them, you’ll definitely find some unique souvenirs to bring home with you!
Mr. Weenie’s Waffles
Amid the historic and iconic buildings, the cobblestoned streets, and classical/romantic balconies is a little store called Mr. Weenie’s Waffles on Calle de San Francisco.
They make and sell hot waffles in the shape of male and female genitalia. The former looks creepily accurate.
I wish I was present in the room when the order for a custom waffle mold was placed.
“Yes sir, that’s right — No, I am not joking. I am very serious. A very serious business man. Yes, I intend to sell …waffles.”
They also sell bikinis, underwear, and other cute accessories. While you peruse, the vibe is nice and casual and the smell is like warm, vanilla sugar.
Unfortunately, we didn’t purchase any waffles, but Katie did buy some cute novelty socks for presents — patterns included roosters, bumble bees, and cocktail shrimps.
Dim Sum
Leaving Viejo San Juan, we took an Uber into Condado for dim sum brunch at New Taste.
Two pork buns, four steamed siu mai, and one spicy girl roll later, our adventure together had come to an end.
I was heading to the Museum of Art of Puerto Rico in Santurce before my flight back to Vieques that evening. It’s $3 admission if you’re a student.
And Katie to her hotel in the Isla Grande area, just minutes from the airport to catch her flight back to Boston the following day.
Reflections
The world has changed a lot in the past several months. These days, travel is much more than an itinerary and a budget.
Everybody has their opinions on the topic, with some frowning upon it while others question lockdown measures. One thinks twice these days.
In Viejo San Juan, there was a good number of visitors there. People from America, as well as local tourists. Everybody was wearing a mask. Temperatures were taken at entrances of establishments. Hand sanitizer proliferates. These are things that have become the norm.
Many, if not all, private businesses were open. Government entities like the Castillo San Felipe del Morro and de San Cristobal were not. One of the guesthouses we stayed at was only booked at half capacity.
In areas that rely on tourism, dollars from visitors are essential to the local economy. And small businesses are stuck between a rock and a hard place of keeping their businesses open at the risk of pissing off locals in the community who don’t want visitors coming in.
As a visitor, I only caught glimpses of this. I had just one experience of feeling unwelcome.
Regulations are constantly in flux and everyone is shifting to accommodate their needs with the changing needs of the environment. The week after I left, a new ordinance shut down beaches in Puerto Rico, except for “exercise”, ahead of the holiday season.
Jim and I are in a unique position as full time housesitters where our lifestyle necessitates travel to an extent. While we don’t have a home base to hunker down, we are lucky to secure opportunities that keep us in one spot for months at a time.
The several platforms we use to find these housesitting gigs have remained active throughout COVID-19. From March, when lockdown measures began in the U.S., to today. For one reason or another, some of us have never stopped traveling.
