My brother and I once got a midnight tour of Old San Juan from a Puerto Rican gangster. He took a liking to us in a hole-in-the-wall bar off the beaten tourist track. We probably should have noticed his status in the community by the way that the locals reacted to him as he sauntered into the dirty place and hung up his fedora. However, in our typical sibling tradition-one of us had fallen for the bartender so we were well into shameless flirting and receiving free cocktails. Hence-we were the two whitest, tipsiest patrons of the establishment. I blame my bro; for it was he who had fallen for the woman who kept refilling our drinks after his red-headed brain told him ridiculous tipping was a fantastic idea. But I digress, back to the gangster.
He walked in and a seat opened next to us as the previous tenant instantly vacated the stool in order to please our future tour guide. My brother, well into his mode of mingling with locals, instantly patted him on the back and asked him how he was doing. It was clear this guy was not used to such blatant idiocy flaunted in his face. However, something about our moronic grins and chatty nature appealed to him, and soon the man was ordering rounds of shots and asking us about our travels.
Let’s call him Slick, shall we? He was donning a fantastically tailored suit, full with suspenders, a cigar, and of course-the fedora. So for the purpose of my story, lets agree that Slick is an appropriate title.
It just so happened that our parents had sent us out that evening in search of good tips for a traditional local restaurant for my fathers birthday. They wanted something genuine, not too touristy, and of course-delicious. When I mentioned this to Slick, his eyes instantly lit up. Three shots of tequila were ordered, and Slick moved between my brother and I, arms over both of us, cigar dangling-and said:
‘why it just so happens I own the oldest restaurant in town’
Several cocktails and a headache later, my brother and I returned to the hotel. We had been promised full-treatment for the whole family the next evening, and Slick went above and beyond in delivering his word.
The hostess was awaiting us at eight the next evening, with a special room prepared. My parents were treated amazingly, with little stories about each of the dishes and the history of the restaurant. After dinner, kid-ginger and I were invited out to drinks back at the same bar from the previous evening. Two hours later, we returned to the now closed restaurant where my brother was given full reigns of the bar, and I watched in amazement as Slick pulled out a book that looked like it belonged on a pirate ship. Inside it were the autographs of hundreds of celebrities, some of them old-glamour Hollywood who had frequented the establishment.
Slick handed us each a pen, had us sign it (which we both found insane as clearly we are all-but celebrity material), and then announced that if we wanted to see the real Old San Juan, he was the best tour-guide in town.
So it was that we walked until the sun came up through the cobblestone streets. Slick pointed out various sites, and even got us into the front lawn a government residency after a small word with the police guards in front of it. There were amazing gardens inside, and he insisted we wander through them. Everywhere he took us, people moved aside for Slick. We received drinks, stories, and a tremendous amount of laughter before the night was through. Naturally, we applauded ourselves as we stumbled back to the hotel on the joys of mingling with the locals when traveling.
It was one of the greatest travel nights I’ve ever had. Just goes to show what a smile, a bit of ignorance, and a gangster can get you in Puerto Rico.