The Tastiest Caribbean Cocktails to Make at Home

I have read the entire oeuvre of Hunter S. Thompson, my literary hero. In The Proud Highway, a collection of his letters, the eccentric writer claimed that his muse came in a “rum-flavored rage.” Hailing from Kentucky, Thompson’s darling was bourbon, but he spent years in Puerto Rico as a reporter for the San Juan Star. I like to believe that his sojourn in the Caribbean turned him into something of a lifelong connoisseur of cane spirits.

As a fellow Southern gentleman, I second Thompson’s conviction about the supremacy of bourbon. But I see rum and whiskey as close kin. The best rums age for years in ex-bourbon barrels, often sourced from Kentucky legends like Woodford Reserve and Jim Beam. Both classes of spirits are liquid amber sparkling with whiffs of white flowers, vanilla, and coffee—olfactory poems that slowly unfurl in the glass.

I wouldn’t live to see my fortieth birthday if I emulated all of Thompson’s habits, but I can get behind using rum as a creative catalyst. When I savor it at home, I usually whip up one of these six Caribbean-inspired cocktails. Sip them on the patio on a hot afternoon, at the beach house, or late at night as you write to stave off the Fear. And by all means, raise a glass to HST, who I trust is throwing back daiquiris right now with Hemingway and Burroughs in some smoky corner of heaven.

If you like piña coladas and getting lost in the rain—if you’re not into yoga and you have half a brain—then you’ll love this classic recipe. Legend claims that the Puerto Rican pirate Roberto Cofresí invented the piña colada, though several bartenders in Puerto Rico also stake their claim to its creation.

You can substitute dark rum in the recipe, but you won’t get that delightful, halcyon hue evocative of the sunshine on the beaches of Vieques. Coconut cream can overpower the nuances of white rum, so go with something bold and assertive. I’m partial to Diplomático Planas, a Venezuelan white rum with enough backbone to stand up to the cocktail’s sweetness. A tropical garnish isn’t required, but an edible orchid adds a nice splash of whimsy and color.

Blitz all ingredients in a blender with crushed ice until smooth. Serve in a chilled hurricane glass. Garnish with an orchid and a pineapple wedge.

This cocktail is a riff on the time-honored Jungle Bird—but with more hair on its chest. If F. Scott Fitzgerald were the Jungle Bird, then Hunter S. Thompson would be the Jungle Beast.

Crafted in Trinidad and Tobago, Kraken Black Spiced Rum is a top-notch cane spirit infused with a medley of hard spices like clove, nutmeg, and cinnamon. It’s as complex as a fine amaro, and I like to pour myself a neat glass to sip with my Jungle Beast. For the Italian bitter liqueur, I stick with the staples: Campari or Aperol.

Combine all ingredients in a tiki glass filled with crushed ice. Stir gently. Garnish with palm leaves and a fresh pineapple wedge—or whatever jungle flair you can find in your kitchen or garden.

Puerto Rico is home to Bacardi, one of the world’s largest rum producers, but La Isla Encantada also boasts a long and venerable tradition of small-batch craft rum. After a stint in France, Ron del Barrilito founder Pedro Fernández applied cognac-making techniques to rum making. The brand ages its rum in ex-Oloroso sherry barrels—some of the world’s most coveted and expensive casks.

Ron del Barrilito brims with notes of crushed cacao, aromas accentuated by the recipe’s chocolate bitters. Chocoholic that I am, I tend to go heavy on the chocolate bitters and lighter on the orange. For the simple syrup, I make my own every few weeks on the stovetop and keep a batch in a mason jar in the fridge. Optional but highly encouraged: blast Gasolina by Daddy Yankee as you prepare this tippler.

Pour all of the ingredients into a mixing glass and add ice. Stir for 10 seconds and strain into an Old Fashioned glass with fresh ice. Squeeze orange peel over the glass and place it on top as garnish.

If Kid Rock can call himself a cowboy, then so can I, goddammit. This cocktail is equal parts Western and tropical—like a love affair between Cody Jinks, the outlaw country singer, and Karol G, the sultry reggaetonera. The recipe is quick and easy, and it’s the refresher I make when I’m feeling lazy—or viciously hungover.

Proudly crafted in the Cowboy State, Wyoming Whiskey is as bold and elegant as the Grand Tetons. It’s important to use a high-quality fruit juice—something free of corn syrup and artificial preservatives. I’m partial to Langers, a family-owned juice company from California.

Fill a rocks glass with ice. Add whiskey and juice. Stir gently and garnish with pineapple and jalapeño slices.

Under the spell of an ill-conceived Kerouacian fantasy, I worked on farms in Hawaiʻī during college. The abundant sunshine and volcanic soil simply makes produce taste better—everything from pineapples and mangos to coffee and tomatoes. Sugarcane is no exception, and Kōloa Rum distills nothing but the choicest Hawaiian cane. I steer clear of rums laden with artificial flavorings (they taste foul and precipitate murderous hangovers), but Kōloa’s coconut-flavored rum is tinctured with the Real McCoy—Hawaiian coconut extract.

The daiquiri is a simple cocktail, but it’s deceptively tricky to master. Bartender buddies tell me that whenever they want to size up a fellow bartender’s chops, they order a daiquiri. This recipe is a slight riff on the classic, made with Kōloa’s coconut rum in place of white rum.

In a cocktail shaker, combine the rum, lime juice, and simple syrup. Shake well with ice, then strain into a chilled coupe glass.

For my money, Trini food is woefully underrated. Trinidad is melting pot of Spain, India, and West Africa, and its cuisine amalgamates South Asian spices with European technique and Caribbean ingredients. Born and raised in Trinidad, Cyllan Hicks, the bartender at Nothing Really Matters in Times Square, brings that delectable Indo-Caribbean flair to his mixology. The last time I visited, I left him a 50% tip just to wrangle the recipe for his iconic Chai Tai.

If you’re an ambitious at-home mixologist, make a foam from orgeat—a French almond liqueur with a name I love for reasons only a therapist could explain. If you’re less crafty, just add a dash of plain orgeat and call it a day. Dona Chai Masala is my favorite chai concentrate, but if you can’t find it, grocery store chai mixes work in a pinch. The Chairman’s Reserve Spiced Rum is also key here: this St. Lucia-made spirit includes the usual spices along with “Boise Bande,” a local bark that’s considered to be an aphrodisiac. 

For the foam, combine the almond milk, white sugar, almond extract, and orange blossom water in a blender. Blend until the sugar is fully dissolved. Pour the mixture into a storage container. The orgeat should last up to two weeks when stored in the refrigerator.

Add the spiced rum and chai masala to a cocktail shaker. Fill the shaker with ice and shake hard for about 5 seconds. Strain the mixture into a highball glass filled with ice. Top with orgeat foam or a dash or plain orgeat.