Puerto Rico lived in Hunter Thompson’s mind long after he left San Juan. That’s the nature of the place. Manic, sweat dripping, rum soaked paradise that it is. It’s not an easy city to leave unscathed from. This is a city with a pulse that beats fast; it’s a rhythm to live up to; a salaciousness of the salsa shaking variety to contend with.
Puerto Rico is a place where the rum runs free, the music plays loud and hedonistic adventure thrives. The legal drinking age is 18. The mandatory skirt length is minimal. And the culture is a complex melding pot of all that is provocative. For the novice, this is a place that can eat you up at night and spit you out in the morning. We recommend it wholeheartedly.
4 P.M. Ron del Barrilito Distillery
In a sense, San Juan is still sleeping at this time. The bars may be open, but they’ve yet to be filled by the hordes of locals, hedonists and cruise ship vacationers that will descend on the city when dusk falls. It’s only fitting your night should begin with a lesson in rum. You will be drinking a lot of it. Schedule a tour with Federico Hernandez, the third generation owner at the Ron del Barrilito Distillery. Nearly impossible to find outside of Puerto Rico, Ron del Barrilito may not be the largest brand but it’s fiercely guarded recipe is close to the best.
5:25 P.M. El Batey
Some dive bars are merely a trend in dive clothing. The tables aren’t rickety enough, the patrons aren’t wild enough and the graffiti is too painstaking. But El Batey is a dive bar for the most discriminating bar fly. Don’t let the bars on the windows deter you; this is the place for $4 drinks, cheap pool and 25 cent songs on the jukebox. This is also the place to get you prepared for your next stop.
7:50 P.M. Club Gallistico: Cockfighting
Not for the weak of heart, animal lovers, the subdued or submissive, slow or those adverse to the word ‘cockspurs;’ cockfighting is alive and legal in Puerto Rico. North Americans may find it a ruthless and inhumane sport, but cockfighting is deeply entrenched in Puerto Rican culture. The action outside of the ring is nearly as brutal as inside with bets screamed out until accepted by someone else in the crowd. There are no house bets, no house rules. But be forewarned, these gentleman’s bets are taken seriously by the locals. Beer, served to you by ring girls, will only run you about $3 here – cheaper than most places on the island.
9:20 P.M. Calle San Sabastian
Head to the cobble stone street of San Sabastian, where bars line either side of the road. Now is the time to flit from bar to bar. Whatever your poison may be, San Sabastian will have it. Drinks are no longer cheap but the parade of miniskirts and heels will soften that blow.
10:30 P.M. Jose Enrique
Adrenaline charged, alcohol coursing through your blood; with your night only now opening in front of you, it’s time to eat. Restaurant Jose Enrique is packed with locals. But if you can find this well hidden, yellow house with no sign, it will be worth it. Stripped of most any tourist trapping; the menu is scrawled on a blackboard, the food is Puerto Rican and the wall art is in chalk. Reservations are not taken and precedence may be given to friends of the owner. But one bite of the asopao (a heavy stew) and you’ll be ready for whatever else San Juan plans to throw at you.
12:45 A.M. Club Lazer
At midnight clubs in San Juan are still rubbing their eyes awake, an hour later and they are packed and spilling onto the sidewalks. Club Lazer is three floors of Reggaeton, hip hop and house music. The crowd tends towards the young side, but at this point in the night it doesn’t matter.
4 A.M. El San Juan Hotel and Casino
Put some money down, and then watch the sun come up; that’s the only way to end your night. El San Juan Hotel is where the past and present have merged into over 13, 000 square feet of casino. This is the old world of Rat Pack revelers to today’s Brat Pack wannabes. When you can’t focus on your cards anymore, head up to the rooftop terrace to watch the sun come up.