24 Hours in Condado, San Juan (November 2020)

My favorite way to explore a city is by bike.

Whizzing by pedestrians and cars, wheels churning interminably fast, it is akin to flying.

When access to pedal power is unavailable, another favored option is to run.

It feels a bit more salt of the earth to use my two feet. Honest transportation. No devilish wheels here!

And so it came to be that shortly upon arrival in the Condado neighborhood of San Juan, Puerto Rico I lace up my sneakers at the time of day when afternoon is settling into evening and the streets are abuzz with energy.

The Route

My route through Condado makes a large and winding figure eight through town. Come with me as I run around Ashford Avenue and Calle Loíza.

We’ll stop by the following beaches:

Take pictures at these landmarks:

Shop at local businesses and eat at local restaurants:

Ashford Avenue

My starting point on Ashford Avenue is a trendy, commercial area.

The kind of place with an oceanfront Marriott and a two-story Starbucks. Where you can buy a bowl of poke or a bowl of acai. Gutters are clean, sidewalks broad, and young tourists in their holiday best zip by on rental scooters. The app is Skootel and they’re all over San Juan.

Things get decidedly less coiffed traveling eastbound on Ashford towards Calle Loíza, a strip dotted with hipster shops, vintage stores, local eats, and street art.

My favorite kind of place. The kind with a hard edge and flowers blooming out its heart. Lots of gum, lots of tags, a little bit grungy, a bit trashed; subversive, artsy, eclectic, cool, and weird.

Libros Libres

Starting at the west end of Calle Loíza I immediately strike gold in the form of a stunning pile of books shelved in stacked milk crates along an exterior wall, beneath an awning. It appears a disheveled mess but upon closer inspection the books are generally in good condition.

I see books about all sorts of topics written in Spanish and English. Occasionally, another language surfaces, like German.

There’s a wide selection of books here. Everything from guides to rock-climbing in Colorado to textbooks on microbiology to history of 19th century art. Meditation pamphlets to Bibles to books on magic. Too many fiction novels to count and an equally large selection of children’s books.

Sifting through the stacks, I resist being greedy. I am a voracious reader who loves books. A man next to me appears to share my predilection as he has almost 10 or more books loaded in his arms.

I bring home a thick book called A Course in Miracles, Volume II.

Google Maps has this location tagged twice — once in Spanish and once in English.

  1. Libros Libres
  2. Free books on the street’ (Hahaha!)

Graffiti and Street Art

Continuing eastbound down Loíza, there are lots of local restaurants, artistic and politically charged graffiti, and colorful buildings and street art. This gives me a taste of the neighborhood flavor.

Loiza Street Station

When I reach a McDonald’s on a corner, I notice the flavor is changing.

It is becoming less artistic and more urban so I make a left onto Calle Santa Cecilia and head westbound down Calle McLeary.

I pass a hostel, Villa Eshta, that sits behind a fence. Later in my trip, I consider staying there.

Rising above the shorter surrounding structures is an intimidating building emblazoned with ‘Loíza Street Station’ so I stop to take a picture.

Wondering if it is a metro stop, I check the map. Unfortunately, it’s just the post office. There is no subway in San Juan, but there is a bus system.


It’s been a while since I’ve been on a long run but I’m keeping a steady speed this evening.

I enjoy running past people meandering on the sidewalks and cars backed up at stoplights, listening to Deep House music and feeling my paced breathing while winding through the streets of this big city.

My stride is in constant flux. I sprint through crosswalks and slow jog through blocks to catch my breath.

I look for stairs to run up and down, I balance on curbs, and jump onto street benches that look too high for me. It takes me back to when I was a kid and the world was a playground.

This is why I like to run in cities and the woods. Fuck treadmills.

Cannabis Use

Speaking of play, I catch the whiff of nice, potent ganja and look around. Up ahead is a modern, green facility with a medical logo — Bwell Healing Center. In Puerto Rico, marijuana for medicinal use has been legalized, but recreational use remains illegal.

Nevertheless, I smell it on the streets of the city from time to time and no one seems to pay it much mind. There is much of the same casual attitude here as in most liberal parts of the US.

Thrift Stores in San Juan

Along Calle Loíza are two thrift stores. The first is Vice Versa, aka the best thrift store I’ve ever been to. And this girl has been to many.

Most of the items are not inexpensive, but they are well-marked for their value. Anything from gently used Marc Jacobs to new-with-tags Free People or vintage Chloé.

Their shoe selection is on point and if this were an earlier period of my life, I would be all over a pair of cream-colored, patent-leather Prada platform mules.

In addition to clothing, they carry a menagerie of furniture and decor. The employees are stylish and sweet. And another consideration unique to secondhand shops is it doesn’t smell like a thrift store.

My friend, Katie, got some great finds here, a fiery orange blouse and a present for me — an electric-green silk nightie tiger-striped with midnight-blue.

For the rest of our stay, we rocked our thrift store finds every day. Two splashes of Blood-Orange and Electric-Green bopping around San Juan!

The other thrift store, Electroshock, is also on Calle Loíza and an entirely different experience. Designer brands do not proliferate. Less designer more hipster chic.

There is a really hot, short bandeau skirt that would be fun to wear if I had somewhere to wear it to. Alas, those days of warehouse parties are over so I place it back on the rack and instead pick up a cool pair of yellow cat-eye shades.

To the side are some skater t-shirts presumably designed by a local artist with subversive graphics about smoking blunts and tripping on psychedelics. I’m tempted to pick one up for Jim because the graphics are cool except I can’t imagine him wearing it.

Ocean Beach West

Around a corner, a few pretty, barefoot girls with beach chairs strapped to their backs come into view.

Curious, I run down the road they just came from, Calle Atlantic Place. At the end, there is a hidden entrance to Ocean Beach West.

When I step onto the sand, it’s expansive and open, unlike the city streets I just came from.

Quickly, I slip off my socks and sneakers and jog down to the water.

A little white dog follows a little boy. Friends and family and couples are gathered in their own tidal pools of love and towels and coolers. The din of laughter, shouts, and waves mix with the dimming light.

Kite Surfing & People-Watching at Numero Uno

Next door is Numero Uno Beach House, a hotel, restaurant, and kite-surfing school all rolled into one.

One afternoon I spend a few hours writing and drinking tequila while Katie takes kite-surfing lessons. Ah, Puerto Rico!

They have seating right on the beach, friendly staff, and a menu with tons of healthy options. It’s a great place to hang out and people watch.

While I was there, the owner’s wife came by to take pictures for their Instagram so I got a front row seat to the teachers showing off their kites in the wind. Good vibes.

La Punta Surf Spot and Punta Piedrita

Running on my forefeet in the sand stretches out my arches and I revel in the feeling.

Years ago, I read about barefoot running in the book, Born to Run by Christopher McDougall. Running is a primal instinct. I can’t help it.

Further along the beach, I spy surfers bobbing in the troughs and crests of the waves — La Punta Surf Spot. I slow down to watch them. It’s a dream of mine to surf one day.

Another runner catches up to and passes me, exchanging a few friendly words. He stops to stretch at Punta Piedrita, where the land sticks out like a bone spur.

A group of teenagers sit coolly against a large wall covered in graffiti abutting a few high-rises. They stare as I run past and around the point.

Exit Strategy

The rocks are sharp and I clamber carefully over them, passing two men with fishing lines cast into the sea. They caution me to watch the tide.

I’ve only run a few hundred feet when a severe rock bluff blocks my traverse along the beach.

I hate backtracking.

Noticing a pair of sneakers and legs sticking out from under a tree and shrubbery at the top of the steep and prickly bluff, I head towards them.

They belong to a sullen teenager smoking a cigarette. We exchange smiles and I disappear into the bushes, rustling through a short trail before popping out onto a quiet street with high-rise buildings, where Calle Condina turns into Paseo Don Juan.

In just a short block, I link back to Ashford Avenue, almost exactly where I started my running tour of Condado. I turn the other way down Ashford, westbound, to Puente Dos Hermanos, the bridge to Old San Juan.

This is the area of Condado where stylish resorts live. I sprint past their manicured exteriors of large stone slabs and dominating facades.

Energy of the Street

The streets are packed. It’s Election Night.

People wave green flags with white stripes out their car windows. Pretty girls fly by on scooters, whooping and shouting, the stream of a green flag in their wake. Men sell flowers in the street.

People honk their horns and I stop to stare, grinning and taking pictures. They smile back at me, elated and full of pride.

They are waving flags of the Independence Party. In Puerto Rico there are 6 parties and this one is fighting for independence from the US.

My mind turns to the mainland that is run by bipartisan politics and wonder what a difference a multi-party system would make.

La Ventana al Mar and Parque Pasivo de Condado (Parks)

The evening is churning like my thoughts as I turn into a large beachfront park called La Ventana al Mar, the “Window to the Sea”.

It’s a pretty park that has all sorts of structures for me to jump onto and work my coordination. I spy a Ben & Jerry’s behind some flowers.

Lots of people mill around here, talking and hanging out with friends. Skaters dominate a corner of the park, sliding down rails and kick-flipping over stairs.

Past them is a concrete deck that walks into the ocean. At its entrance, a group of men puff on a joint and smile as I run past. The tile is slick with ocean spray so I slow my pace. Couples take pictures and old men huddle in conversation. I take a panorama on my phone of this evening scene.

A few minutes down Ashford is another park, Parque Pasivo de Condado. It’s smaller than La Ventana but there’s a great statue of a big woman that catches my eye.

There are plenty of benches to sit and watch the traffic go by.

Playita del Condado, Laguna del Condado, and Puente Dos Hermanos

Where the bridge (Puente Dos Hermanos) begins there is a sandy beach adjacent to the road. It’s unexpected so it feels almost secretive but there are many people here swimming.

A couple of boys jump off the bridge into the waters below. Across the way are views of the historic Fortin San Jeronimo de Boqueron.

Here at Playita del Condado the waters are calm unlike Ocean Beach West, which is much more surfy. A natural reef lies where the ocean comes inland and breaks the waves. The rocky barrier is somewhat famous and one of the rocks is called La Piedra del Perro.

According to this website, the name comes from a local folk tale of a fisherman who had a dog companion he always brought with him fishing. One day, the fisherman doesn’t bring his dog with him and drowns alone at sea. His dog continues to wait for his master to return, steadfast and patient. Que romántico.

On the other side of the bridge is Laguna del Condado. During the day, SUPs and kayaks dot the water, lending a pretty view for those traversing the bridge. At its banks is a grassy knoll where people hang up hammocks and chill. It would be a nice place to chill and people watch. Bring a book if you’re alone or hang with some friends.

Night in Condado

At the end of the bridge, I turn around. At this point, I’ve run almost 5 miles. Night has fallen and lights rise to take their place in the show.

Walking through Condado at night, you can see where people congregate to eat and drink. It’s lively and I enjoy weaving through the crowds of laughter and the aromatics of delicious food.

Tacos at Kabanas

That night, we eat at Kabanas, an open-air taco joint that Katie says is a must.

Lucky timing, it’s Taco Tuesday so tacos are $2.22. We both order one of each: pork, beef, falafel, veggie, and chicken, which are listed here in order of my most to least favorite. Katie likes the falafel the best.

While everything is delicious, the tortilla is amaze-balls. It’s a soft-ish taco shell that I’m pretty sure has been dusted in powder cheese cocaine and fried, resulting in some delicately and decadently cheesy crusted, chewy but crispy tortilla.

Unfortunately, I don’t take any pictures because I like to eat and pictures are the last thing on my mind.

Dim Sum at New Taste

Near the resorts is a small Chinese restaurant, New Taste, that has a wide patio overlooking the busy street for optimal people watching.

On my second to last day in San Juan, we order the steamed BBQ pork bun, steamed siu mai, and the spicy girl roll. Everything is delicious, especially the house roll.

It’s a chill place and I can see myself spending an afternoon here writing on my laptop, eating Asian tapas, and drinking bubble tea.

Museo de Arte de Puerto Rico

The last place I want to bring you on this virtual tour of Condado is the Museum of Art of Puerto Rico.

Actually, I didn’t pass this on my running route but it is definitely within running distance.

It is worth it to come see the art of Puerto Rico. Whilst walking around a museum, I see the colors, the strokes, the medium, and I get an understanding of the culture and the people through osmosis of perception.

All the same, it is perception and perception is the lens of my own story. For that matter, it was helpful that I met Jose upon arrival at the museum.

Jose is a friendly, older gentleman working at the Information Desk in the quiet lobby. He walks me over to the enormous stained-glass wall behind him, explaining its symbolic Taino meaning.

“Tainos were our ancestral Indians … So the big circle is the sun when it goes up and the circle in the middle is the sun when it goes down … There is a line at the top of the big circle from right to left — that’s our main mountain that goes from east to west … The blue lines at the top represent the sky and the blue lines at the bottom represent the sea.”

There were many pieces that caught my attention, but I will share just a few here.

One was a series of seven silkscreens by Jack and Irene Delano that depict the history of indigenous Taino meeting Spanish conquistadors.

Another is a painting of a scene in Puerto Rico from the Spanish-American war where locals show American soldiers another passage through the land, assisting them in an important battle.

These two selections stir up strong emotions around the brutality of colonialism by conquering nations.

Recent American colonization that followed the Spanish-American war is often mischaracterized by history. For more information on this topic, read about Pedro Albizu Campos and for more information about Puerto Rico under America’s rule, go to this link.

My favorite piece of all was an installation that occupied a small room. It was decorated in the style of a ‘New Yorican’ barber shop (a moniker coined by the artist).

Commentary on the machismo culture of Puerto Rico, it was replete with hubcaps, pool table, velvet-red barber shop chairs, a statuette of Jesus dying on the cross with synthetic flowers at his feet.

A larger than life “tattoo” was stenciled on the wall with the words “Perdoname Madre” — Forgive me, Mother — next to a pair of roses and bullets.

It felt eerie and sad and I was magnetized, drawn even closer to the “touch guy” display that was so deeply vulnerable at the same time. The heartache was palpable.

An Identity

Leaving the museum, I came to know Puerto Rico as a relatively new culture.

According to some historians, feelings of a united identity in Puerto Rico only came together in the late 18th century when England invaded.

At that time, the “criollo” population (people born in Puerto Rico after colonization) banded together in San Juan to protect their land from the British who had the most powerful navy in the world at the time (see picture for source).

Today, all throughout San Juan are signs of this national pride. Flags are draped from windows in high-rises, spray painted on abandoned walls, and miniature versions dangle off rearview mirrors in cars.

There’s a unique history to the island. One that starts with the land, for which many cultures clashed— the indigenous Taino, who called the island Boriken, welcomed the Spanish when they landed and, when asked, freely shared where to find gold.

Christopher Columbus named the island San Juan Bautista, but soon after it was colonized, Puerto Rico was given its current name, which means “rich port” because of its resources, including gold dripping through its rivers.

Not only did its multitude of resources draw people to its shores, but its location within the sea made it a desirable post for many countries.

For its strategic location between Europe and the Americas, it was known as the gateway to the new world. This is why Spain fought for 400 years to keep it (source below).

Modern Age

The new San Juan can be seen in Condado.

The people are beautiful and fashionable, the residences modern and sleek, the cars fast, and one can tell there is money in the city.

It is a busy metropolitan here with art, culture, food, and entertainment.

It’s a city with a story. But the story starts in Old San Juan, where the Spanish landed more than five centuries ago.

The next day, I pack up my things and head to the cobble-stoned streets of Old San Juan, located across Puente dos Hermanos.

Let’s go on a walking tour tomorrow and I’ll show you the beautiful streets through my eyes, my friend.



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