The Rum Diary
Credit: Everett

In the spring of 1959, a brash young reporter named Hunter S. Thompson was fired from his New York newspaper job after he vandalized the office candy machine because it ate two of his nickels. Thompson escaped to Puerto Rico, where he took a job at a bowling magazine, lived on the beach with his common-law wife in a two-room shack, and spent nights swimming naked and drinking cheap rum. Six months later, out of work and facing a year in jail after a scuffle with the cops, he packed his duffel bag and fled the island on a sailboat. He was not yet 23.

Thompson had mixed feelings about his time in Puerto Rico, calling it "rotten" but reveling in its idyllic areas. It gave him enough material for his first book, The Rum Diary — "the Great Puerto Rican Novel," as he called it. It was a dizzying time to be on the island — the dawn of the great tourist boom, with lots of gleaming new high-rises and yanquis with cash to spend. In October, as a movie version of the book starring Johnny Depp hit theaters, we revisited Thompson's old haunts — to find what was left of his Puerto Rico after a half century of the growth and development he fueled and feared.

The Heart of San Juan, Then and Now
My trip got off to a Thompsonesque start, as I arrived in San Juan straight off a three-day bachelor party in Las Vegas. Still dazed and wobbly, I headed directly for the Caribe Hilton, the oceanfront resort Thompson called the "corner­stone of The Boom." The Hilton once played host to all manner of movers and shakers, hustlers and crooks, and although the casino is now closed and the private beach sees more yoga moms than sunbathing starlets, the place maintains some of its glamour — a telenovela bombshell here, a pro-soccer team there. But this was no time for poolside celebrity spotting: As Thompson wrote, "Arriving half-drunk in a foreign place is hard on the nerves. You have a feeling that something is wrong, that you can't get a grip." I took his advice and went straight to sleep.

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The next morning, fortified by a typical Thompson breakfast (toast, "an eye-opening swim" in the Atlantic, fresh pineapple, and four cups of coffee), I strolled up to Calle Tetuán, where The Rum Diary's narrator, a Thompson-like newspaperman named Paul Kemp, kept an apartment — "a dank grotto in the very bowels of the Old City." There was nothing dank about the city on this morning. Amorous couples and pigeons congregated, and, two blocks away, La Bombonera, the landmark cafe that Thompson fictionalized as La Bomba, still serves the best café con leche in town.

Chasing Al's — And Other Great Dives
The truth is, a lot of Old San Juan has changed, the salsa bars and colmados having long since given way to American-style dance clubs and Hard Rock Cafes. But there are still a few spots where the old San Juanero spirit lives on. The Parrot Club is a classy old restaurante — where Depp dined during filming — whose plantain-crusted dorado and stiff rum cocktails are excellent. Up the hill is El Batey, a dive bar with $2 beers and graffiti covering its cavelike interior. Down the street, Thompson historians can't miss El Patio de Sam, whose banana-yellow walls and lazy ceiling fans inspired Al's Backyard, the Rum Diary hangout that provided a counterweight to the "high-price ‘New York' bars that were springing up all over the city like a rash of neon toadstools." For a place that's even more Al's than Al's, meanwhile, there's El Hamburger, a greasy, locals-only spot where a fist-size cheeseburger and a heaping basket of fries will set you back just $4.75, plus another $2.75 for an ice-cold Medalla.

Searching for Puerto Rican Rum
A central part of The Rum Diary is, of course, the rum. In Puerto Rico, Thompson did his share of boozing: "The drinking would begin at noon," he wrote. "It made the day go a little faster." His drink of choice was rum on the rocks — a modest luxury at a time when a bottle cost a dollar, and a bag of ice, two.

Corporatization and consolidation have impacted rum in Puerto Rico just as they have everywhere, leaving most small distillers dwarfed by the Bacardis and Captain Morgans, as well as local favorite DonQ. Thompson's beloved Ron Superior has been out of business since 1980, so I paid a visit to El Ron Del Barrilito, a family-owned distillery in the Bayamón district. There, the Fernández brothers blend their smoky-sweet concoction using the same recipe their grandfather set down when he opened in 1880 and the same plants their ancestors tended in the 1790s. They're bittersweet memories, though; now most of the sugar for Puerto Rican rum is grown in countries like the Dominican Republic.

Shacks and Beaches, Untouched
Before long, I realized that in order to really take to Thompson's Puerto Rico, I had to get out of town. My last morning on the island, I rented a car and drove to the village of Loíza Aldea, 15 miles east of San Juan. It's an easy jaunt down the curvy, two-lane blacktop of Carretera 187, but in Thompson's day, it was only accessible by a rough sand road — "like something hacked out of a Philippine jungle" — which was still visible through the palm trees alongside the highway.

There are no Hard Rock Cafes in Loíza Aldea. In fact, there are few tourists. Instead, there are roadside stands selling fried alcapurrias and sun-bronzed natives sipping coco frío fresh off the tree. In the novel, a character named Yeamon lived out here, where he fished for lobster with a speargun and played coconut football in the surf. The real-life Thompson lived here as well, on a secluded beach near a long rock reef, and although it isn't certain his particular pillbox still stands among the many paint-peeled shacks, the place he described is instantly recognizable. I could almost see him smoking his pipe in the shade, as I lunched on crab tacos and beer on the beach and followed it up with a brisk ocean dip — "feeling for the first time," as Thompson wrote, "…that I had actually come to the Caribbean."