Best Cigar & Spirit Pairings for Father’s Day

Best Cigar & Spirit Pairings for Father’s Day

A good drink and a solid cigar. 

There are few duos that can evoke sophistication, grit, and a touch of bravado like a cigar in one hand and a drink in the other. They call to mind men of history like Winston Churchill, Mark Twain, and even Marlon Brando in “The Godfather”. It’s worth noting that as we celebrate Father’s Day this year, the tradition of cigars goes back centuries, much like your family tree. The word itself first started floating around in the English language in the 1730’s. So as you plan gifts for Father’s Day, think of our guide as a map to your perfect cigar and drink pairing. We’ve curated this list to suit a variety of tastes, with a spectrum of options for different prices and pours. Whether you use these ideas for a great Dad in your life, to celebrate your own fatherhood adventures, or to raise a glass and a stogie in memory of a loved one…we’ve got you covered. 

In fact, we’ve added a bit of the history behind each cigar choice…cigar-making is often a multi-generational family affair, and the stories behind these smokes can give you a great narrative to share on Father’s Day. These stories are the “why” behind the cigar “what”. 

The Classic Aficionado: Cigar and Scotch

It’s traditional, and somehow both refined and rugged. A cigar and scotch pairing is a solid match, where master distillers meet master cigar-makers. Both carry the essence of heritage, perfect for a Father’s Day gift. 

Romeo y Julieta 1875 + Oban 14

The Cigar: Romeo y Julieta 1875 While the brand’s fame rose when it became Winston Churchill’s cigar of choice, this family-run operation has stayed steady in popularity, and the 1875 is a classic, medium-bodied choice that will be appreciated by aficionados and by those who are just learning how to smoke a cigar. The earthy, slightly woodsy flavor flows into a mild sweetness. 

The Spirit: Oban 14 From the Scottish highlands, Oban 14 is a well-balanced, medium-flavored Scotch. It’s dependable, straightforward, and won’t compete with a cigar unnecessarily, but holds its own nicely. Know anyone like that? As a single malt, this slightly sweet, slightly smoky Scotch stays true on the palate, balancing the Romeo y Julieta 1875 from start to finish.

The American Cowboy: Cigar and American Whiskey

Cowboys, cigars, Clint Eastwood…there’s a vibe here. It’s yours for the taking. Or the gifting, because a solid cigar and an American whiskey sound like you just won Father’s Day. 

Oliva Serie V Melanio Maduro Robusto + Woodford Reserve Double Oaked

The Cigar: Oliva Serie V Melanio Maduro Robusto Think leather, coffee, mocha, and earthy spice. This is our pick for a maduro cigar that can hold its own. It’s medium-bodied and nuanced, but it doesn’t try too hard. Oliva has been crafting its cigars since 1886, and this version is an easy, deliciously flavorful smoke. 


The Spirit: Woodford Reserve Double Oaked It’s got range. The second aging brings the caramel, the toastiness, the heft, and the smooth oak finish all in line. This bourbon won’t overpower your Oliva cigar, because it will stand up next to it like a solid deputy…albeit one with its own idea of how things should taste. 


El Conquistador: Cigar and Tequila

If you haven’t tried tequila with your cigar, what a perfect opportunity to dive into a new adventure. General rule of thumb: Mild cigars pair best with a slightly more complex, aged tequila. 

Padrón Dámaso + Roca Patrón Reposado

The Cigar: Padrón Dámaso We love a good origin story. A patriarch of the Padrón family, Dámaso arrived in Cuba from the Canary Islands in the 1800’s. This cigar, named in his honor, joins the well-respected lineup of Padrón smokes. A perfect cigar for tequila thanks to its lighter profile (rare for a Padrón!), it’s flavorful and mild for its style, with a creamy, buttery smoke and subtly sweet layers of toasted nuts and cedar that roll into a bit of spice. 


The Spirit: Roca Patrón Reposado Because this tequila is aged for a brief but effective five months, it carries woody elements swept up in vanilla, agave, and caramel with a surprisingly smooth, crisp finish and the right nudge of heat. Roca Patrón is the artisanal version of Patrón’s brand, and it shows. Enjoy the way this tequila punches up the flavors of our cigar choice.  


The Havana: Cigar and Rum

Cigars and rum…they originate in similar regions, and can both trace their lineages back centuries. It only makes sense they’d find each other a smooth fit, especially when their strengths aren’t battling one another, but drifting together with rich flavors that balance the other. A nice metaphor for Father’s Day, if we do say so ourselves.

My Father Jaime Garcia Especial + Zacapa 23

The Cigar: My Father Jaime Garcia Especial There’s a poignancy here, perfect for Father’s Day: the legendary Pepin family makes the My Father brand of cigars, and this specific cigar is crafted by the next generation. Don Pepin’s son, Jaime Garcia, blends this cigar himself, and it was a sort of debut for him as a solo effort. We can all relate. That first time you try to do something your father, uncle, or grandfather did so well…and you nail it. You get to take a deep breath and grin as they congratulate you, or you know they would if they could see it. Now imagine Don Pepin’s pride when his son knocks his first solo cigar out of the park. Jaime’s blend creates a profile of deep espresso, earthy cedar, toasty hazelnut, and delicate pepper. It’s a full-flavored cigar in a super gordo size, so you can enjoy it for over an hour.


The Spirit: Zacapa 23 Much like the balance of young and old, Zacapa 23’s age balances the heft of the solid cigar we chose. This Guatemalan rum delivers honeyed notes, with smooth caramel alongside a rich molasses element and just a hint of smoke and spice to balance the cigar above. Smooth enough to drink neat, or with a single ice cube to bring the flavors forward.


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