You won’t find much fear and loathing these days in Old San Juan, but there are places where you can still get a taste of the city where “gonzo journalist” and author Hunter S. Thompson decamped in his early 20s to work as a newspaper reporter after getting fired from another paper in upstate New York for trashing an office candy machine.
The year was 1960, and this was Thompson’s first big foray into the wider world to work, drink rum, and soak up the sun and (at least some of) the local culture. Serendipitously, his editor ended up being William J. Kennedy, who would go on to win the Pulitzer Prize for his 1983 novel, Ironwood.
Thompson and Kennedy became friends, piling up adventures together that would eventually help form to write “the Great Puerto Rican Novel” based on Thompson’s island experiences.
It must have been quite the post-trip hangover, because the semi-autobiographical book, The Rum Diary, took another 38 years to get published; a movie version starring Johnny Depp as Paul Kemp, a New York reporter in Puerto Rico, followed in 2011.
Puerto Rico simmered with tension at the time of Thompson’s arrival: the previous decade has seen police massacre nationalist protestors in the streets of Ponce and an armed attack on the Old San Juan residence of the governor, the ancient Fortaleza. Even the now-ubiquitous Puerto Rican flag was banned under pain of imprisonment for anyone who dared display it.
Today, as in the 1950s, the streets of Old San Juan are full of hole-in-the-wall bars as well as more refined drinking establishments. In the Rum Diary, Paul Kemp can be found at the Al’s Backyard bar when he’s not chasing women or dodging police and thugs. The fictional bar is based on the real-life El Patio de Sam, a favorite hangout of Thompson’s that’s still serving Puerto Rican food like mofongo and skirt steak along with burgers and a good beer selection, with seating in a courtyard enclosed by the yellow walls referenced in the book as well as on the Plaza de San Jose.
Nearly everything in Old San Juan is, well, old — the city dates to 1521 — but Thompson’s nine-month residency in the city corresponded with a growing boom in tourism, and there are many midcentury landmarks that would have been familiar to the author. The Caribe Hilton, opened in 1949, served as both home base and shooting location for the Rum Diary movie (it’s also where one of the world’s most famous rum drinks, the Pina Colada, was reputedly invented in 1954, although El Barrachina in San Juan has an equally valid claim).
A movie star like Depp, but probably not an ink-stained wretch like Thompson, would have been welcomed at the Condado Vanderbilt Hotel, opened in 1919 as Puerto Rico’s first luxury hotel (and casino) and still awash in Art Deco style. Like the Vanderbilt, the landmark Antiguo Casino de Puerto Rico doesn’t have gaming now; built in 1917, the Beaux Arts building was the home of the Puerto Rican Institute of Culture — a place Thompson probably could have benefitted from visiting occasionally — and is currently an event venue.
Interestingly, the hotel pictured on the cover of the Rum Diary, with Thompson lounging on a beach chair, isn’t in Puerto Rico at all: it’s the Aruba Caribbean Hotel (now the Hilton Aruba) on Palm Beach, where Thompson spent time in 1962.
The 2011 film was shot on location all over Old San Juan as well as on El Convento Beach in Fajardo and in the north shore town of Vega Baja. The latter was the stand-in for scenes involving Kemp’s beach house; in the book, however, the house is in Loiza Aldea — not coincidentally the same place that Thompson himself occasionally crashed on the beach. Located on the eastern outskirts of San Juan, Loiza is famous for its beach shacks, called chinchorros, grilled meats and other traditional island food, as well as its Afro-Caribbean culture.
In his book, Thompson describes the ‘degenerate’ character Moberg frequenting the “dirtiest bars in La Perla,” and while this commune just outside the walls of the old city isn’t as dangerous as it once was, tourists are still advised to steel clear of the neighborhood at night. More welcoming to travelers and Thompson fans are classic Old San Juan bars like El Batey, another Thompson hangout on Cristo Street with graffiti-covered walls, a famously retro jukebox, and strong drinks made with local (non Bacardi) rums like Barrelito and Ron Hacienda Santa Ana (Thompson’s favorite, Ron Superior, was off the market for years but is poised for a return to Puerto Rico’s bars).
The Parrot Club restaurant, a favorite of Johnny Depp during filming of Rum Diary, sadly closed in 2022 after 21 years in business. But La Mallorquina, old even in the 1950s, is still going strong on Calle San Justo. Specializing in Puerto Rican and Mallorcan food, the restaurant dates to 1848.
After dinner, walk (or, if you really want to channel your inner Thompson, stumble) off the meal on the historic cobblestone streets of Old San Juan; it’s just a one-minute stroll to Calle Tetuán, where you can amuse yourself by trying to guess which apartment Thompson envisioned as belonging to Sala, a character in the book but also the author’s real-life roommate in Puerto Rico. Thompson described it as “as homey as a cave, a dank grotto in the very bowels of the Old City,” though like most of Old San Juan it’s probably improved considerably in the intervening years.
