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An old Spanish Plaza in Old San Juan.

Richard, the live-in staff member I had checked in with the night before had recommended that the best way to see the whole of the city was to take the T-5 bus, which was supposed to loop through Isla Verde and most of the downtown area.  Conveniently, its route also went down Ponce De Leon.

So, my first morning, I got up and headed over across the street from Denny’s to catch the T-5 west.  Aside from the fact that I probably should have gotten on the East route, I soon came to love this bus driver.  The bus only took exact change, something I didn’t have, so he let me on anyway.

He continued on to give me the most entertaining ride I had been on in a long time.  Weaving in and out of traffic, cutting off anyone that got in the way of his big bus.  Honk, Honk, Honk, HONK at a double parker blocking the whole lane until he pretty much got close enough that she would be plowed out of the way unless she moved.

The trip concluded at the SE corner of the Old Town island, something I wasn’t expecting, but I figured it was as good a time as any to explore Old Town.  Leaving the central terminal, I saw an enormous cruise ship, The World, docked in the distance.  I later looked it upto find that it was a year-round luxury residence ship which circumnavigates the globe.

My first sight after leaving the bus station.

‘The World’ luxury residence ship docked in Old San Juan.

To my right was a strip of restaurants along an open air plaza.  I picked a random one and entered another bar/convenience store.  As I sipped on the Medalla and a couple kids came in to buy milk, I asked the owner what restaurant was good around there, to which he simply responded with a great smile, “Todos!”

The Chuleta Can Can at Raices. Thank you Man vs. Food.

So all of them were worth eating at, but I had my heart set on Raices, ever since seeing it featured on Man vs. Food, a guilty pleasure of mine during my winter in the Upper Peninsula.  I quickly found it a couple blocks over, but decided to wait until a little later to eat.

The southern shore was only a couple blocks away, so I headed for that.  Here was docked that giant cruise ship, dwarfing any buildings in the immediate area.  Hugging the shore, I came to a dead end at the Coast Guard post, complete with a stern warning that I would be entering a military facility were I to continue any further.  Alongside it was an almost Spanish-colonial looking complex with was mostly empty but was featuring a small art exhibit from Spanish artists, which I was very impressed with in this odd location.

Continuing along the shore, I came to the beautiful trail alongthe city wall.  Aside from being littered with derelict kites and stray cats (water and food spaced randomly for them too) It was an absolutely amazing path along the old Spanish colonial barrier.  The idea of the outmoded nature of those city walls these days is perhaps just a small sign of progress that Humans have made in the last couple hundred years.A section of the beatiful pathway along the outer wall.

The San Juan Gate along the west wall.

Eventually I had to backtrack when the path came to a dead end at the fort and returned to the city through the San Juan Gate.  Here, I was thrown into the heart of Old Town.   Slopes and brightly colored, pastel buildings and gated off courtyards I wish I could have gotten into; all these I passed as I wandered the streets.

The El Castillo from below.

Eventually, I came to the highlight of Old Town, El Castillo de Filipe del Moro.  It was a This path led me toward Filipe del Moro, a fantastic maze of several ramps, levels and rooms.  Unlike a lot of similar historic sites I had been to, many of the secondary rooms were open to the public.

The massive cemetery on the north side.

The deteriorating La Perla outside the northern city walls.

From the Castillo, I continued along the north side of the wall to San Cristobal.  There is quite a noticeable difference between the building inside the wall and those on the north coast outside the wall, a neighborhood called La Perla, being something you could almost consider slums.  I was warned that I should stay within the walls on the north side of Old San Juan, and as interesting as the neighborhood looked, I chose to heed the warning.  Some great insights into La Perla can be found in this article.

I didn’t go into San Cristobal, figuring it would be similar enough to the last fort.  Instead I passed it and began zigzagging down random streets through the main body of Old Town.  Eventually, needing some water, I went into an open air bar and ordered a Medalla and a water.

The Castillo of San Cristobal.

A statue of Abraham Lincoln outside of a school.

A Dominican came in and sat next to me and we got into a fairly decent conversation in Spanish.  He was in San Juan working on the King Tut exhibit, which I unfortunately didn’t get around to seeing.   He even asked me what kind of music I liked and offered to go over to the jukebox to start playing it, which I refused, as I was leaving quickly.

A random roadway in Old San Juan.

Another hour of walking through the grid streets of Old Town and it was starting to get dark.  I looped through a new path toward the bus terminal though into Puerta de Tierra, the Capitol district.  It seemed an interesting area, and there was some large citadel-type structure over it, but I didn’t get a clear look at what it was.

I caught one of the last buses back to the hostel’s area of town.  I stopped at a gas station on the walk back and picked up a can of Chef-Boyardee and d a six-pack of Medalla.

Upon arriving at the hostel, Robert and I talked for a couple hours over those beers about everything from San Juan to archaeology to science fiction.  He had grown up at a military base on the eastern shore of Puerto Rico, so he had some useful insights into the Island and the city.

He found it a little sad that San Juan is kind of a dying city, with Old Town in particular.  At first I thought he meant the limited space, when he mentioned that the only reason it survives anymore is because of the cruise ship tourists docking there.  But he pointed to several people and properties that he knows on the Old Town island that just are simply doing nothing to attract the business that is out there to be had.

Another American that I met a few days later would seem to back this up, that the city is simply dying on jobs in his attempt to find one anywhere on the island.

Benjamin Williams

Hi all, my name is Ben. I’m a native Michigander with a passion for human culture and new places, and more than that, new experiences. I have degrees in archaeology and writing, pursuing a career in the latter. However, I never quite lost that fascination for archaeological theory. For the past 11 years, I’ve been living and travelling between Asia, Europe, and North America, documenting ancient sites and the peoples who built them, and then adapting them into practical archaeological travel information at

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