Cocktail of the Month: Calle Ocho Old-Fashioned
By • April 14, 2026 0 1387
There’s one street in Miami that moves differently than the others. People sashay to a salsa beat. Men in guayabera shirts and straw hats play dominoes with tiles that number up to nine per square. Cigar shops with seasoned torcedors hand-rolling stogies in the windows line the sidewalk.
Welcome to Calle Ocho (Southwest Eighth Street) in Miami’s Little Havana. Cuban music rules and the watering holes specialize in Cuba Libres, daiquiris and mojitos. Perhaps one of the most storied places to find live music and cocktails is the Ball & Chain bar, often referred to as the heart of this district.
The Ball & Chain opened in 1935, not long after Prohibition. The bar has changed hands over the years, but perhaps the most interesting chapter in its history started in the 1950s, when it was purchased by Ray Miller and Henry Schechtman. According to his sons, Schechtman dealt in stolen liquor and bootleg cigarettes, was part of a Jewish mob and served prison time.
At that time, the Ball & Chain was a pioneering entertainment venue. Among the stellar Black performers who headlined were Louis Armstrong, Count Basie, Nat King Cole, Ella Fitzgerald, Billie Holiday and Lena Horne. Trumpeter and singer Chet Baker appeared in 1957, the year the club closed, only to reopen in 2014.
The neighborhood also changed during this era. By the end of the 1950s, a large number of Cubans, fleeing the dictatorship of Fulgencio Batista and, later, Fidel Castro, poured into the area. By 1967, the strong Cuban presence in the community prompted Miamians to refer to the area as Little Havana and to its main thoroughfare as Calle Ocho.
I stumbled into this legendary bar last November during a quick stopover in the Magic City, where I met up with two of my besties: Roger Krisko, a Homeland Security executive, and Mari Garcia, a partner in one of Miami’s top advertising agencies. As we rambled along this cultural avenue, we were drawn in by the live music, the festive vibes and a 2-for-1 happy hour special.
While my friends went for the Ball & Chain’s signature mojitos, I was attracted to the bar’s intriguing version of an Old-Fashioned, which fuses three Cuban staples — rum, tobacco and demerara sugar — into a single cocktail.
One thing I noticed was the precision of the bartenders. Men with deep lines etched into their smiles (not the Botox-smooth, Mar-a-Lago faces of South Florida) blended and muddled our drinks with care. Each glass felt like it was served with a meticulous, authentic vibe.
The main component was Bacardi 8 rum. Originally a Cuban brand, Bacardi moved to Puerto Rico and became a global conglomerate, producing some rather mediocre spirits. However, their eight-year-aged rum works well in cocktails with its oakiness and hints of apricot and nutmeg.
Tobacco was represented in two ways: with infused bitters and a dried leaf (mostly likely from one of the neighboring cigar factories) to serve as a garnish. While the bitters are made in house, similar products can be purchased online.
The third element was demerara sugar, a type of natural, unrefined cane sugar often imported from the Caribbean. Its large, crunchy, light-brown crystals and molasses flavor made it a perfect foil for the rum and the bitters. Cuba is sometimes called “The Sugar Bowl of the World,” highlighting its historical role as a leading sugar producer.
The result was an alluring tipple with a smoky earthiness from the tobacco and a cutting smack from the rum, tempered by the candied sugar — something delightful to sip on languidly as we played catch-up while grooving to the Latino beats.
“What I really enjoyed about Little Havana is that you can tell you’ve entered a totally unique neighborhood,” said Roger, a first-time visitor. “Music floats into the streets and the smell of strong Cuban coffee lingers in the air. Cuban tradition is something you can taste, hear and feel.”
Calle Ocho Old-Fashioned
2.5 oz. Bacardi 8 rum
1.5 oz. demerara sugar
3 dashes tobacco bitters
Place sugar and bitters in a rocks glass and muddle until dissolved. Add rum and a large ice cube. Let sit for 20 seconds to chill. Garnish with a tobacco leaf.
