How to Experience Hunter Thompson’s Puerto Rico

Rum in the Sun!

In 1959, Hunter S. Thompson put Puerto Rico on the literary map. Many will recognize Thompson as the “Gonzo” journalist and author of The Rum Diaries (made into a movie of the same title starring Johnny Depp).

I’d love to set the clock back to 1950s Puerto Rico. The 1950s was a dizzying time to be on the island. It was the dawn of “American Caribbean” tourism, with gleaming new high-rises, free-flowing rum, and maverick writers cranking out stories on Remington typewriters.

But since time only moves forward, we’ll have to travel back to Hunter S. Thompson’s Puerto Rico vicariously. Join me (cybernetically). I’ll show you where to find the local haunts and hangouts which Thompson made famous. And, if you love dressing vintage, like I do, read on for some suggestions on how you can have fun with 1950s travel clothing.

The Beginning of an Era

 It’s the spring of 1959. A brash twenty-two-year-old reporter named Hunter S. Thompson is fired from his New York newspaper job after he vandalizes the office candy machine. In a fit of rage, Thompson takes off for Puerto Rico. With a glass of rum on the rocks and an old typewriter, he begins work on The Rum Diary — or as he called it, “The Great Puerto Rican Novel.”  The novel mirrors Thompson’s own experiences working as a journalist in San Juan through the turbulent, alcohol-imbued escapades of its narrator, Paul Kemp.

We’re going to follow in the footsteps of both the author and his narrator. But first, let’s put together our vintage wardrobe. Links will bring you to sites where you can purchase clothing or be inspired to put together your own vintage wardrobe.

The 1950s Gonzo Journalist Style

Guys, if you want to conjure Thompson’s boozy, tropical, 50s American journalist style, here’s what you’ll need.

• A Classic Cream Panama Hat  
• Brown Polarized Ray-Ban Aviator Shades
• If you really want to capture Thompson’s unique style, check out “The Clothes of Hunter S. Thompson” (Love that rakish cigarette holder)!

The 1950s Chic Caribbean Tourist Style

Ladies, here’s what you’ll need to be both comfortable and glamorous in our retro literary tour of Puerto Rico.

• Slim cigarette pants — or high-waisted, knee-length shorts — are iconic 1950s casual wear.
• A button-down halter neck top, skinny belt, and ballet flats will complete the look.
• For dinner, have fun with a vintage cocktail dress. Not formal, not informal, the cocktail dress is perfect for that pre-dinner piňa colada.
• If you want to go full 50s, find a pair of nude backseam stockings, strappy heeled shoes, and a small crescent hat.
• For help with your wardrobe, go to “50 Vintage Inspired Clothing Brands and Stores.”
• Don’t forget to pack the cat eye sunglasses and a vintage sailor pinup swimsuit.
• For help with 50s hairstyles and makeup, go to “Authentic 1950s Makeup History and Tutorial.”

How to Visit The Rum Diary Haunts and Hangouts in Old San Juan

Morning

• Pick up a copy of The San Juan Star from your hotel lobby — In The Rum Diaries, narrator Jack Kemp worked as a young American journalist for a floundering English language newspaper, a fictionalized version of the still-in-print The San Juan Star.
• Walk along Calle Tetuán. With your copy of The San Juan Star, head for Calle Tetuán, where Paul Kemp kept an apartment — “a dank grotto in the very bowels of the Old City.”
• Eat Breakfast at La Bombonera (259 Calle San Francisco) — Two streets up on Calle San Francisco, stop and enjoy a typical Thompson breakfast (toast, fresh pineapple, and four cups of coffee) at La Bombonera, the 1902 landmark cafe that Thompson fictionalized as La Bomba in The Rum Diaries. It still serves the best café con leche in town. But instead of boring toast, try La Bombonera’s famous mallorcas, warm pastries filled with ham and cheese.
• Explore Old City Streets — I know we’re trying to follow in the footsteps of Hunter S. Thompson, but unless you have a high tolerance for caffeine, DO NOT drink four cups of Puerto Rican coffee. It’s really strong. You’ll be bouncing down the cobblestone streets of Old San Juan. You don’t want to do that. Old San Juan is a UNESCO World Heritage Site. It deserves to be appreciated. Take your time strolling past historic churches, colorful colonial buildings, and local craft stores. You’ll be glad you did.
• Gaze out upon the Caribe Hilton (1 Calle San Gerónimo) — If you walk to the top of the hill, as Paul Kemp did, you can look out on the harbor for which Puerto Rico is named (Rich Port). From this vantage point, you’ll see one of Hunter S. Thompson’s favorite haunts.

The Caribe Hilton is an expansive oceanfront resort that once played host to all manner of movers and shakers, hustlers, and crooks. Although the casino is now closed and the private beach sees more families than sunbathing starlets, the Caribe Hilton maintains much of the glamour — and the price tag — of its historic heyday.

For budget-conscience travelers, consider one of the many guesthouses near Paul Kemp’s Calle Tetuán. One of my favorites is La Terraza de San Juan (262 Calle Sol).

By noon, you may be ready for the feature focus of The Rum Diary. 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 of rum cost a dollar, and a bag of ice, two.

Noon  

• Have lunch at El Patio de Sam (102 Calle San Sebastián) — You’ll pay a bit more for your glass of rum at El Patio de Sam, a local restaurant/bar that will forever be associated with Thompson’s rum-swilling days. The restaurant’s banana-yellow walls and lazy ceiling fans inspired Al’s Backyard, The Rum Diary hangout that provided a low-cost alternative to the “high-price ‘New York’ bars that were springing up all over the city like a rash of neon toadstools.” Not quite as budget friendly as it was in Thompson’s day (but still as Americanized), you can expect to spend between $6-$7 for a rum-based drink.

While El Patio de Sam is part of literary history, for more local flare, go for the chinchorros scattered around Old San Juan. These tiny hole-in-the-wall bars offer cheap drinks, few American tourists, and a window into local life. With their colorful ambiance and local rum, they are the sort of places Hunter S. Thompson would have frequented.

Afternoon

Where to Find Local Chinchorros in Old San Juan

• Colmado Bar Moreno (361 Calle Tetuán) plays Reggaetón and serves strong rum in plastic cups. Ask for Don Q — the popular local rum inspired by Miguel de Cervantes’s iconic literary character, Don Quijote.
• Los Tres Cuernos (359 Calle San Francisco) — Tucked away in a carnival mask shop on Plaza de Colón, this local dive has the best chichaitos — a shot of rum and anise flavored with fruit juice.
• El Batey (101 Calle Cristo) is as close to Paul Kemp’s San Juan as it gets. Drinkers are encouraged to write on the walls (Revelers have been known to form human pyramids to get to clear writing space) and an old jukebox plays vinyl 45s from the 1960s.

While Hunter S. Thompson and Jack Kemp could easily have spent the rest of the afternoon drinking rum in the local chinchorros, you might want some down time. But when the day is over and it’s time for dinner, Caribbean spiny lobster must be on the menu. It’s written about extensively in The Rum Diaries and is a Caribbean delicacy. To understand the difference between New England and Caribbean lobster, read “Caribbean Lobsters — Not Your Average Main Lobster.”

Evening

Where to Eat Local Lobster in Old San Juan

• El Asador (350 Calle San Francisco) — Lobster is not a budget choice anywhere, but if you’re going to splurge on dinner, do it 50s style. Put on that cocktail dress and dinner jacket and stroll arm-in-arm to El Asador, a romantic grill and seafood restaurant directly in front of San Francisco church. Dine to the sound of church bells in a Spanish colonial building designed around an interior patio. Enjoy a crisp Albariňo while savoring risotto with lobster or mofongo de mariscos (mashed plantains fried and served with local seafood). Plates vary between $24-$26.

Eating lobster, drinking rum, and visiting local chinchorros are all must-do Rum Diaries experiences. But to really get a feel for Hunter S. Thompson’s Puerto Rico, you need to get out of town. Fifteen miles east of San Juan is the village of Loíza Aldea, where Thompson lived in a two-room shack on the beach — “spending his nights swimming naked and drinking cheap rum with his common-law wife.”

Ladies, put on your cat-eye sunglasses and head scarves. Guys, take out those brown-tinted aviator shades. We’re taking a road trip to rural Puerto Rico.

The Next Day

The Rum Diary Rural Hangouts, Loíza Aldea

• Cruise Down Carretera 187 — Getting to Loíza Aldea is an easy ride down the curvy, two-lane highway, Carretera 187. But in Thompson’s day, the village was only accessible by a rough sand road — “like something hacked out of a Philippine jungle.”
• Snack at Local Chinchorro Stands — There are few tourists in Loíza Aldea. Instead, there are roadside chinchorro stands selling fried alcapurrias (fritters made of green bananas and taro root stuffed with meat)and refreshing coco frío (cold coconut served with a straw).
• Learn About Local Lobster Fishing — In The Rum Diaries, a character named Yeamon lived in Loíza Aldea. He fished for lobster with a speargun and played coconut football in the surf. For an incredible underwater video of local fishermen hunting for Caribbean spiny lobster, see this amazing clip.
• Spend the day at Río Grande Beach — Maybe you’re not adept with a speargun (how many of us are?), but you can re-create Hunter S. Thompson’s Puerto Rico. Pack a local lunch of empanadillas (fried meat pies), and surullitos (fried corn sticks). Laze on the white sand beach, read a good book, and contemplate the beauty that inspired Hunter S. Thompson to “feel for the first time that he had actually come to the Caribbean.”

For writers and artists, there is inspiration in the turquoise waters and colorful villages of Puerto Rico. As Hunter S.Thompson once wrote, “There is something fresh and crisp about the first hours of a Caribbean day, a happy anticipation that something is about to happen, maybe just up the street or around the next corner.”

Puerto Rico has changed a lot since Thompson was a young journalist working on his “Great Puerto Rican Novel.” And while it will never be the same, you can visit the old haunts and — just for a moment — transport yourself back in time and imagine what it was like to experience Hunter S. Thompson’s Puerto Rico.

What would it take to bring YOU to the island? Getting fired from your job could work, but hopefully that will not be the reason!