Viejo San Juan (Old San Juan) and La Perla

We spent three afternoons and evenings in Viejo San Juan, the old part of Puerto Rico’s capital city, though Helen was sick the last time and stayed in the hotel room trying to recover. I’m going to mix all three days together and not bother about which pictures were taken on which days. I like Viejo San Juan a lot, myself; but it helps to know its history. Also it helps to know about La Perla (as you will by the end of this post) before you get there.

Christopher Columbus came across Puerto Rico on his second voyage, but it was Ponce de León who settled the place. The harbor that is now known as San Juan Harbor (full name la Bahia de San Juan el Bautista) is one of the world’s best natural harbors, and its strategic importance in the days of sailing vessels would be difficult to overstate. Before steam engines you couldn’t fight the trade winds; it is actually not possible properly to understand the history of European Atlantic trade, including the history of the slave trade, if you don’t know that sailing ships in the Atlantic pretty much had to travel around the Atlantic in a clockwise circle. Puerto Rico is the first large island with timber and fresh water that you get to when sailing the westward portion of that circle, and its immense harbor offered unparalleled protection both from weather and enemies – as long as you could keep the enemies from getting through the half-mile-wide entrance to the harbor. If you controlled San Juan Harbor you could control much of the Caribbean in the caravel and clipper ages. And thanks to the not-very-bright but very-very-very-lucky Columbus, Spain got there first.

San Juan Harbor consists of two critical features. The first is the huge bay itself, which extends well back into the island with plenty of room to hold entire fleets of vessels all at once. The second is the island of San Juan Bautista, which sits directly across the mouth of the bay and blocks all entrance thereunto except for a half-mile strait at the western tip of the island – on the east, the extremely narrow channel is not navigable for ocean-going vessels. And the island itself rises precipitously from the sea to a commanding height, with a rocky, wave-battered coast that offers no place for invaders to land an invasion force, while providing all the room for defensively emplaced cannon you could ask for.

De León’s first choice for where to build a Spanish settlement in San Juan Harbor was not a great one – for reasons I don’t pretend to understand, he first settled at Caparra on the interior of the bay – but he eventually realized his mistake and moved everybody across to the island. And the town of San Juan, or at least the part that sits on the island to this day and is known as Viejo (“Old”) San Juan, has been there ever since. The Spanish held on to Puerto Rico and San Juan longer than to any other of their American possessions save Cuba; San Juan was subject to the Spanish crown all the way up until the Americans took the town and the island in 1898, during the Spanish-American War.

And for most of those four centuries, Spain was building fortifications. And not measly little twenty-foot-high, six-foot-wide fortifications like, say, the old city wall of York, from the days before Europeans had found out about gunpowder. These are fortifications built specifically to ward off sixteen-pounder cannon fire from entire fleets of enemy men-o’-war. The walls are fifteen to twenty feet thick, and in places a hundred feet high.

Castillo San Felipe del Murro, from second highest level

Upper levels of Castillo San Felipe, from within second-level fortifications

The Castillo San Felipe has four levels, all with cannon emplacements and those twenty-foot-thick walls, which is the biggest reason that when Sir Francis Drake decided to come sack San Juan with a fleet of twenty-seven ships he got well and truly spanked, so that the next time the British decided to try their luck, they used an army rather than a navy, landed them on shore well away from San Juan’s guns, and attacked from land. The only fortifications I’ve personally seen that can compare are the Ming city walls in Beijing (or what little remains after the wanton vandalism of the Chinese Communist Party during the Great Leap Forward and the following two decades); but the Chinese cheated by having a hundred million or so disposable peasants on hand to build things with. The Spanish were so enthusiastic about the San Juan fortifications, and had so many decades in which to indulge their enthusiasm, that the first defensive tower they built wound up being completely inside one of the later walls. I don’t mean that they built a wall between the old tower and the sea. I mean that they built a new wall around and over the old tower so high and so thick that now what used to be the old tower is a room inside the new wall.

Castillo San Felipe del Murro, display

That’s what most people remember when they come back from San Juan: the Castillo San Cristóbal that guarded the eastern end of the island from land-based attack, the Castillo San Felipe del Murro that still bestrides the western end lest the harbor be attacked from the sea, and the mostly-intact city wall that encircled the island and left no place where the two Castillos might be circumvented. At the southeastern corner the walls got torn down in order to allow expansion, before Puerto Rico fully grasped the economic importance of tourism and the historical pricelessness of the wall. Otherwise, they are intact, and very much worth your time, O Gentle Reader.

Castillo San Felipe del Murro, stairs down from upper level

Castillo San Felipe del Murro, stairs down from upper level


Castillo San Cristobal


City walls near Castillo San Cristóbal 

We got there in the early afternoon, and found an underground parking garage at the far western end of town, right next to the Castillo San Felipe (the bigger one, guarding the mouth of the harbor). Parking is at such a premium that there were attendants down there explicitly commanding you to double-park and block earlier arrivals in. They then let you keep your keys so I suppose if said earlier arrivals wanted to also be earlier departures… (helpless shrug). I figured we’d be there for a while and folks would have cleared out by the time we wanted to leave; so I didn’t worry about it, and we walked out of the garage into the sunshine.

Now the first thing I noticed was the Cementerio Santa Maria Magdalena de Pazzis, where the Spanish have been burying good (and, to judge from the statuary, wealthy) Catholics since the days of Ponce de León. On that first day we didn’t go down there, because Helen wasn’t very interested, and also I mistakenly thought you could get there from the Castillo San Felipe. So we just took photographs from the city wall.

Cementerio Santa María Magdalena de Pazzis from east (1)

Cementerio Santa María Magdalena de Pazzis from east

I went down there on the last day, while Helen was asleep in the hotel room, and walked down the street and through the tunnel that allows cars into the cemetery and from there into the neighborhood of La Perla; but I got there too late and the gate was locked. IMG_3310

Still, I was close enough to see some of the statuary close at hand. And also, I noticed something I hadn’t thought to predict, but that made sense as soon as I saw it. The graves do not, generally speaking, have the names of individuals on them, the way tombstones do here. Instead, they simply say, for example, “LA FAMILIA ­­­­­_____” – that is, they are family crypts.


Cementerio Santa Maria Magdalena de Pazzio (3)

On that first day, though, we walked up the hill to Castillo San Felipe, paid our money, and went in. And I will spare you most of the details of the tour; you should go there yourself someday. I do, however, have to show you at least one picture of the sentry boxes that are more or less the national symbol of Puerto Rico – which I could do, actually, simply by showing you a picture of a Puerto Rican license plate. The entire city wall is studded with these little turreted one-man towers that extend out from the city wall to provide an unobstructed view of anything or anybody that might be approaching; and as always when visiting old fortifications, we plus-sized Americans are reminded of how much smaller soldiers used to be than they are today.

Castillo San Felipe del Murro, eastmost sentry post, second level from top

Castillo San Felipe del Murro, eastmost sentry post, second level from top. Note that the length of the narrow walkway is precisely the width of the wall.

I also thought the staircases were pretty cool. Each one was different, a different solution to the same basic problem of providing a way for soldiers to hustle from one level to another when under attack. There was a spiral staircase, and a triangular staircase, and even (though this one was so cramped, the Park Service has barred it off) a square staircase for very short people, like I haven’t seen anywhere except in some of the watchtowers on the Great Wall. In fact the staircases reminded me of those watchtowers precisely because each one was different: each of the Great Wall’s watchtowers, too, represents a different solution to the same basic military problem.

Castillo San Felipe del Murro, tiny square-spiral staircase Castillo San Felipe del Murro, triangular staircase (2) Castillo San Felipe del Murro, triangular staircase (3)

Eventually we got hungry, and also we started to get tired of getting intermittently rained on. So we headed for the exit. And when we walked out, with a light coastal breeze dropping raindrops on our heads every now and then and with the sun low in the late afternoon sky, we saw this:

Castillo San Felipe del Murro, half-circle rainbow (2)

We spent the rest of the afternoon walking around in Viejo San Juan, many of whose buildings and all of whose streets are centuries old.

IMG_3486 IMG_3487 IMG_3489

Eventually we wound up down at the bayside shore where the wall was removed, and where now vendors come out daily and set up streetside stalls with popcorn and pizza and tacos and piña coladas. We settled in at one of Juarisco’s outdoor waterside tables. Our nachos took so long to arrive that the manager took them off our bill AND gave us a free shot of tequila; I tried to teach Helen how to do a tequila shot but she thought it got too weird as soon as I started sprinkling salt on my own hand, and I wound up having to drink it myself (since, as befits a man who has been married to a Chinese girl for almost five years, I now consider waste to be a sin).

Then we started to go for a walk along the shore. By this time it was about six-thirty, and as we strolled along the wide sidewalk in the park just below the old city wall, a horrible thought suddenly struck me: what if the parking garage closed?

We hied ourselves over to where a couple of policia were standing, one man and one woman. I told them where we were parked and asked if they knew how late the garage was open, and they both looked at their watches and then they both looked at each other and then they both looked up at us, and not one of those looks was a good one. “They close the gates at six,” the police dude said to me.

“Aw, man, that’s not good,” said I.

The police chick shook her head sympathetically. “That happened to me there once. I had to leave my car there all night.”

Well, we decided to go look for ourselves, and sure enough, as we walked down the ramp, we could see that a steel mesh gate had been drawn completely across the tunnel – right below the sign that said, in big red letters, “Abierto 24 horas”! Up until that point I had been annoyed with myself, but upon seeing a securely locked gate right under an “Open 24 hours” sign, I redirected my ire. But there was nothing to be done about it; so we started to walk back up the ramp, just in time to meet an entire Punjabi tourist family coming down.

Now I was pretty philosophical about it, but the Indian dude was irate, let me tell you. Me, I figured hopping up and down and yelling at nobody in particular wouldn’t do much good; so I told him, “Well, I guess we’ll go find a hotel and spend the night in Old San Juan.”  We exchanged commiserating farewells and off Helen and I trudged, to the nearest hotel, which was El Convento at $200-plus per night for the cheap rooms.

Or at least, that’s what it would have been if they had had any vacancies, which they did not. So I asked the desk clerk, “What other hotels are there? We parked in the garage up under El Murro and even though the sign says, ‘Abierto 24 horas,’ they’ve locked the gate and we can’t get out.”

His eyes opened wide, “Oh no, no, sir, it is open twenty-four hours – there’s another entrance!

He gave us a map and marked where the garage’s other access point was, coming out from underground right next to the Museum of the Americas, and we hightailed it happily in that direction. But first we went back to the one that was locked, hoping to catch our new Indian friends before they spent a few hundred dollars on an unnecessary hotel room…but they were long gone, unsurprisingly. So we hiked around the corner, found the entrance, found our way to the lowest level, and found our car. And just as we were walking up and clicking the unlock button on the electronic key, another car pulled up beside us and rolled down the window – yes, you guessed it, it was the Indian family, who had been looking for us and had given up on us as regretfully as we had given up on them. In their case, the Indian guy had been so furious he had found a policeman to complain to, and this policeman (unlike the tontos we had been so unfortunate as to encounter) had taken them to the other entrance.

I might add that the parking garage actually sits under a plaza where at most times of the day you can find children playing happily in the middle, where one finds an array of about fifty small water jets all shooting straight up the air to about the height of a happy five-year-old’s head. We parked in the same garage a few days later when we spent the evening unexpectedly in San Juan. That was not a very fun day for a lot of reasons, but it ended well. We had dinner at El Jibarito, which looks like a tiny little restaurant from the outside but is surprisingly large once you’re inside, and which serves a very good two-pound fried red snapper (though Helen didn’t care that much for the beef stew). By the time we had finished, it was nine o’clock or so, and we were ready to get back to Fajardo; so we walked back to our car. And as we crossed the plaza, we stopped to watch the children playing there. There was a three-year-old who was in perfect heaven, and an envious child circling the water while pushing his own stroller, having clearly been told by his mother not to go in the water.

But obedience has an expiration date when you are young and the other kids are clearly having so much more fun than you are:

My favorite, though, was that one little dude who looked to be about three. He was in heaven, racing back and forth through the waterspouts at top speed in nothing but his short pants, while his mother and father, whose hands were full of cameras and souvenirs, looked on indulgently. He’s really the reason Helen was videoing those kids; the whole episode with the stroller was an unexpected bonus. Helen stopped videoing after a bit and we just watched him in his joy. Then suddenly he came to a stop in the middle of the water, having come to what clearly seemed to him to be an eminently rational decision – and before his startled parents could do more than utter a squawk of distress and ineffectual forbiddance, with one swift motion he divested himself of the short pants, sprinted past his parents at a run to drop the pants off at his mother’s feet, evaded his father’s desperate one-handed grab, and zoomed happily back into the center of the waterspouts, free and happy as the air. This was all greatly to the delight of all the inhabitants of the plaza, of course, except for his parents. They spent a few hopeless seconds commanding him to come back, which had precisely as much effect as you would expect, and then his father resignedly marched through the water, jeans, camera and all, to retrieve him, which is easier said than it was done since the young man had perfectly good eyesight and was pretty darn quick on his feet.

Now there is one part of old San Juan that I haven’t yet mentioned, and that is the district called La Perla. This is the only part of old San Juan that is actually outside the city walls, and it is notorious throughout Puerto Rico. It’s only about three streets wide, and it’s not that easy to get into it. There is one street that tunnels under the wall in the east…

Calle Bajada Matadera, La Perla, San Juan, from east Calle Bajada Matadera, La Perla, San Juan

and there’s a street that goes over to La Perla from the Cemetery of Mary Magdalene once you’ve gone under the tunnel of the Calle Cementario in the west.

Calle Cementerio, San Juan La Perla, San Juan, western entrance

Then there’s a staircase that goes down the city wall right about in the middle of La Perla…

La Perla, old staircase entrance

and very recently (so recently that Wikipedia doesn’t know about it yet) a brand new staircase has been constructed with funds donated by Carmello Anthony…

Carmelo Anthony staircase, La Perla, San Juan

in conjuction with his renovation of La Perla’s basketball court (now the only nice thing in La Perla except for the drug dealers’ cars, and also the only basketball court in the world that lets you watch a game from a sentry post in a centuries-old Spanish fortification).

Carmelo Anthony court, La Perla, San Juan

So, as I say, not easy to get into – and that’s a bloody good thing because you do not WANT to get into it. The heroine trade within those three or four acres of space is something like twenty million dollars a year, and the murder rate is absurd. Put it this way – for a long time, the maps that the city provided for tourists didn’t show any of La Perla’s streets, in the hopes that if the tourists didn’t know the streets were there, they wouldn’t be tempted in their ignorance to go walk down them and get themselves killed.

In fact I witnessed criminal activity in La Perla with my own eyes:

Respect for the law in La Perla

(That’s a no-parking sign.)

The thing is, you look at La Perla, and you’re thinking that this real estate ought to be some of the most exclusive real estate in Puerto Rico. You already have, for practical purposes, a gated community; it ought to be easier to keep undesirable persons out of La Perla than practically any other place in Puerto Rico. If you took the approach favored by the City of New London – which approach, as we know, has the Supreme Court’s ever-dubious blessing – you could simply condemn every single dwelling under eminent domain, compensate the current residents at current La Perla market values, evict them, renovate the houses, and sell them for a million dollars apiece.

But…that’s not how things have worked out in real history. Instead, since that strip of land was the only part of the island that was outside the city walls, that’s where the Spaniards put the things that you didn’t want inside the city – namely, the cemetery and the slaughterhouses. So La Perla is where the lowest-class people wound up living; it has been a slum and a refuge of outcasts since the first buildings went up there. And while an American investor would look at those immense stone walls and think, “What a great way to keep crime out,” the local authorities have spent the last four centuries using the walls for exactly the opposite purpose: they turn out to be a great way to keep crime in, which is to say, largely confined to La Perla. And so, if you are a tourist, all is well…as long as you know not to drive through those two tunnels or walk down those two staircases.

La Perla, San Juan (2) La Perla, San Juan (3)

Which leads me to one of the nastiest things I’ve seen anybody do on the internet, and the sad thing is I think the guy thought what he was doing was really funny, and not intentionally vicious at all. I think one of the more contemptible expressions of modern American culture arises from the popularity of “pranking” videos. Pranks can be amusing when they are good-natured and harmless. But all too often they are used an excuse to be viciously cruel and bullying to other people who have done no harm.

I had been reading up on the history of Puerto Rico and San Juan and found out about La Perla, and then I started spelunking on the web looking for more information. And I ran across one of those sites where you ask questions and random strangers answer you. Some relatively clueless single college dude posted the following question:

There is so much I want to do while I’m in Puerto Rico. I love a woman with a nice round *** and am interested in the best place strip clubs, and night clubs for women who fit that criteria. We are going out there to party. I am interested in nightclubs and stripclubs. Typical nightlife for college students. People amaze me with ignorant answers!

Don’t ask me what that last sentence is supposed to mean; I don’t know either. At any rate, the highest-rated answer was this:

Get in a TAXI and have the driver take you to the La Perla district… lots of loose women and strip clubs and all the booze and drugs you want… and the people are very nice, they will be happy to show you around… it’s a great place for someone like you to go to.

Oh. My. Goodness. What a nasty, nasty thing to do – and, now, I grant you that I don’t think much of the original questioner and his attitude to women, and it would probably do him some good to have some negative consequences attend his behavior. But there are negative consequences, and then there are Negative Consequences. And this answerer was setting him up for NEGATIVE CONSEQUENCES. The only redeeming element is the fact that he told the tourist to take a taxi, and there is every reason to hope that the taxi driver would refuse to go into La Perla himself, and would happily explain why.

But trusting everything to a random taxi driver is pretty irresponsible; so fortunately somebody else jumped in with a comment to help the original questioner out:

He is joking, La Perla a death trap. No joke, small slum with crazy drug and gang problems. Anyone reading this, do not take serious, for real. It is murder capital of PR.

So there you have it: Go to Puerto Rico; spend a few evenings in Viejo San Juan; stay out of La Perla.

La Perla ends at the foot of the Castillo San Cristobal, and that’s a good place to end your day in San Juan. With the sun behind you, you can look to the east, along the coast at the base of the castillo, and far off by itself, you can see one last, lonely, exposed sentry box.

Garrita del Diablo, San Juan

This is la Garita del Diablo, “the Devil’s Sentry-Box.” It sounded for all the world like somebody was throwing a party on it that last evening of ours in San Juan, but I find it hard to believe the National Park Service would have allowed such a thing. At any rate, this sentry-box was by far the most isolated and exposed of all of San Juan’s garitas, which naturally gave rise to the sentries’ dislike thereof, which in its turn naturally gave rise to the name, which in turn naturally gave rise to legends to explain the name. A typical retelling (along with better pictures than mine) can be found here. But after you read that one, I think the nicest way to finish off our day in San Juan is with this version of the legend, which you can find translated into English here.


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