Go Here: La Perla in San Juan
When you arrive in Old San Juan, it is into the humid bustle of downtown's tourist section. Leave as quickly as the trolly will carry you, you will not experience Puerto Rico at Sombrero Jack’s, and there's a free shuttle begging you to get on.
Get off on St. Sebastian when you stop seeing neon signs on the bars and start seeing faded, colorful paint. Order a drink somewhere near the edge of town in a bar where the crowd is right -- not too young, not too American; you want old and Puerto Rican, trust me.
Look out the window at the ocean because it's darker here than it is in other parts of the Caribbean. That's because it's deeper and drops off suddenly, like the tourist section did as you rode away from it. Finish your drink and don't stay long, but walk toward the ocean to the edge of town as it gets dark, until you see the crumbling tunnel that leads down a steep hill to the walled-in arena of a neighborhood called La Perla. The tunnel is the only way down and the only way back up, too. Remember that as you enter.
In the 19th century, La Perla was a neighborhood created to house former slaves and servants who worked at a nearby slaughterhouse, and it has remained a place of poverty since that time. Laws required that the housing (and it's graveyard) be built outside of city walls, and this is the reason for the tunnel.
Inside La Perla, the light changes from starlight to streetlight. It's likely you'll see no one and be free to wander through the spotlights the street lamps make on the unpaved road. San Juan is full of cats, though. Consider the rate of petty cat crimes, cat burglars, etc, as they lick their paws with sandpaper tongues, lying stereotypically just off-center in the streetlight’s circle. Cats are so dramatic.
La Perla’s houses are painted ornately -- you'll see leopard print roofs and graffiti -- but they are also worn by time and the sandy air, and so their colors are those of nature. Contrasted by the bright, almost fake green grass on the hill before the wall, it is clear that you are past the reach of municipal upkeep.
La Perla is falling into the sea in chunks, making a shoreline of painted concrete blocks, large pebbles, foam. It will convince you that there used to be more of it; another street, claimed by the waves, lying just below the surface like an Egyptian tomb. La Perla is beautiful because it is the real San Juan, and in Puerto Rico they don't try all that hard to hide the truth from tourists.
Walk out past the crumbled houses to the water and you'll find a skate park, with a smooth stone bowl that is painted with an angry, chipping face. On the other side of the bowl, the waves churn but the bowl remains dry.
If there is a Yanni concert at Castillo de San Cristóbal, and it's a good bet that there is, you're in for a treat. San Juan loves Yanni for some reason (pronounced, "Johnny," so for a while I had no idea who they were talking about). Though the police barricades will stop you from getting too close without a buying a ticket (and who would), you can hear plenty of excitement from La Perla's graveyard, where the tombs are massive raised stone boxes, because the ocean is so close that the waves often attempt to disturb the sleep of the dead.
Before you leave San Juan, you may find it necessary to kiss someone near the black Caribbean sea. Don't ignore this impulse -- you're not the first. Learn a lesson from San Juan's bravery and willingness to show it's flaws, to succumb -- La Perla is a lovely place to decide to change.