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Cigar Pairings

Best Cigar and Bourbon Pairings

Holt's Staff Cigar's picture

Holt's Staff

Cigars and bourbon have been at the heart of American audacity for generations. From gunslingers in the early days of the Wild West to executives who clang their crystal rocks glasses in a boardroom toast, a billowing cigar and a stiff whiskey are meant for one another. Whether you’re trotting through the desert on horseback with a flask, chomping on a cigarillo like Clint Eastwood, or you’re puffing away in the back of a stretch limo with a mobile wet bar, you want a cigar and bourbon that display complementary flavors. Bourbon and cigars already taste amazing on their own.

How to Pair Cigars and Bourbon

Bourbon possesses a natural sweetness that melds well with the smoky and spicy taste of a good cigar. When pairing bourbon and cigars, purists prefer their bourbon neat (at room temperature). If you insist on sipping yours on the rocks, we won’t hold it against you. Chilling your bourbon may change the way it mixes with a cigar, but in either case, it’s best to alternate between sipping your whiskey and puffing on your cigar. 

Some simply like to add a few drops of water to “open up” the bourbon a bit. This works well when you sip your bourbon from a brandy snifter, which concentrates the aroma, but it isn’t recommended for higher proof bourbons. Pour yourself a single or a double, swirl the glass slightly, and take in the aroma before you sip it. Cut and light your cigar, and start puffing. Now that we've got the process down, here’s a rock-solid list of the top cigar and bourbon pairings you should try.

#1 - Ashton VSG & Blanton's

Full-bodied and in high demand, Ashton VSG is drawn from a dark and oily Ecuador Sumatra wrapper that houses a delectable blend of premium aged Dominican tobaccos. Flavors display notes of earth, cedar, leather, and spice in a classic cigar that debuted back in 1999 and is handcrafted at the prestigious Fuente factory in the Dominican Republic. 

Blanton’s equally sought-after profile of nutmeg and spices delivers dry notes of vanilla with hints of honey, caramel and corn. This bourbon finishes with medium body and draws out a marvelous spectrum of sweet nuances in Ashton VSG. Together, the two reveal a luscious, woody marriage with savory depth.


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#2 - Arturo Fuente Anejo & Angel's Envy Cask Strength 

Rare and exquisite, Arturo Fuente Anejo is handcrafted from the finest aged Dominican binder and filler tobaccos beneath a dark chocolate-hued Connecticut Broadleaf wrapper that has been slow-aged in a cognac barrel. The result is a medium-bodied treat that offers a luxurious profile of brown sugar, creamy spices, and cocoa with a buttery finish.

Angel’s Envy Cask Strength bears a glimmering amber color with a rich, reddish tone that has been finished in a Port Barrel. This exquisite bourbon emits a delightful panoramic aroma of smoke, leather, tea leaves, wood, and herbs. Notes of cherries, citrus peel, green apple and rock candy characterize an Angel’s Envy profile that measures up perfectly with the creamy, complex taste of Arturo Fuente Anejo.


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#3 - La Aroma de Cuba Mi Amor & Woodford Reserve

Voted as Cigar Aficionado’s ‘#2 Cigar of the Year,’ in its debut year, La Aroma de Cuba Mi Amor is a medium to full-bodied Nicaraguan treasure, blended to perfection. Chocolate-hued wrappers from San Andrés embrace aged Nicaraguan binder and filler tobaccos. Notes of almonds, dark cocoa, spices, and black pepper are topped with hints of black cherries. 

Woodford Reserve, with its honey-amber appearance and strong aromatic blend of vanilla, tobacco, cocoa, and a hint of black pepper, matches up wonderfully with the mix of sweet and spicy flavors La Aroma de Cuba Mi Amor exudes. Chewy notes of cinnamon, cocoa, toffee, and caramel make Woodford Reserve an excellent choice for navigating the distinct transitions only a cigar blended by the legendary Pepin Garcia can offer.


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#4 - Padrón 1964 Anniversary & Knob Creek 

Padrón 1964 Anniversary shows off a classic profile of cayenne and cinnamon with sweet, earthy spices. This top-rated smoke is drawn entirely from Nicaraguan tobaccos that have been gracefully aged to their apex to display a full-bodied, complex portrait that is still quite approachable. 

Knob Creek is a widely distributed bourbon that harbors more than enough character to complement Padron. A copper and amber hue glows with a sweet, woody taste and toasty aroma of nuts and grain. Naturally oaky, Knob Creek accentuates the consistent caramel-like flavors of Padron. Blend this pair of top-sellers on your palate for a refined combination that is full of rich accessibility.


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#5 - Montecristo & Basil Hayden's

A creamy Connecticut Shade wrapper enshrouds a delectable blend of Dominican binder and filler tobaccos that radiate silky notes of cashews, coffee with cream, and a touch of spice in Montecristo. This legendary Cuban-legacy smoke delivers a mild profile that exemplifies the brand’s popular portfolio.
The understated brilliance of Basil Hayden’s effectively complements Montecristo. Its golden amber appearance and an aroma of tea and spices preludes a tasty amalgam of honey, pepper and soft caramels with a buttery finish. Basil Hayden’s is a light-bodied liquor with a gentle and satisfying finish that nicely accompanies a creamy and approachable Montecristo profile.


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#6 - San Cristobal Revelation & Eagle Rare

If medium-bodied cigars are what you crave, San Cristobal Revelation delivers a sophisticated palate of creamy nuances with notes of leather, cedar, caramel, and black pepper that provide an exceedingly smooth and enjoyable smoke handcrafted in Estelí, Nicaragua. A milk chocolate-hued Ecuador Sumatra wrapper leaf conceals a luscious interior of Nicaraguan tobaccos grown on select Garcia family estates.

Eagle Rare encompasses a subtle mix of aromas, ranging from toffee and orange peel, to herbs, honey, leather, and oak. The taste is bold, but not overpowering, resonating with notes of almonds and cocoa. In this pairing, cigar and bourbon converge masterfully with a pleasantly lingering finish that is both sweet and dry.


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#7 - Oliva Serie V Melanio Maduro & Bulleit 

Oliva Serie V Melanio Maduro conveys a succulent, medium to full-bodied Nicaraguan profile with delightful coffee and leather flavors, capped by spicy hints of black pepper. A lustrous San Andrés wrapper hugs an award-winning Oliva recipe with a balanced zest.
An alluring aroma of oak, vanilla, and honey with an infusion of spices forecasts the wildly popular flavors of Bulleit Bourbon. The taste is equal parts oak and smoke, with a dash of vanilla, culminating in a smooth, dry finish with the slightest hint of black cherry and leather. Bulleit and Oliva Serie V Melanio Maduro are an awesome follow-up to a meal of barbequed ribs.


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#8 - My Father Le Bijou 1922 & Booker's

My Father Le Bijou 1922 is an award-winning recipe blended by Jose ‘Pepin’ Garcia in Estelí, Nicaragua, from tobaccos grown on prized Garcia family fields. A Cuban-seed Nicaraguan Oscuro wrapper envelops fillers that radiate with full-bodied flavor. The blend manifests a plethora of peppery spices, semi-sweet cocoa, and earthy notes of espresso beans. It earned a 97-point rating as well as the ‘#1 Cigar of the Year’ title from Cigar Aficionado for 2015.
A deep, rich, smoky amber appearance is a sign of what’s to come with Booker’s. Its strong vanilla and caramel aroma is accented by a hint of charred oak, leading to an intense taste of fruit, tannin, and tobacco. The uncut, unfiltered approach of Booker’s generates a fitting taste to parallel the potency of My Father Le Bijou 1922.


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#9 - Cohiba & Maker's Mark

The esteemed Cuban-legacy Cohiba franchise is handcrafted in the Dominican Republic to an exceptional standard. A diverse panorama of flavors is finished off by a distinctive, yet understated, sweetness thanks to a Cameroon wrapper and well-blended interior tobaccos from the Dominican Republic and Indonesia. Smokey spices with a bit of brown sugar burn smooth and easily.
Maker’s Mark reveals a brilliant orange-flame color in appearance and a distinctive aroma of caramels, honey and pepper. Maker’s is made with wheat instead of rye for a sweeter, less intense delivery. Savor lingering accents of caramel, cinnamon, malt, and vanilla with a creamy nuttiness in conjunction with the crisp spices Cohiba furnishes.


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#10 - Rocky Patel The Edge & Wild Turkey 101

Go for the gusto with Rocky Patel The Edge, a beautifully handmade Honduran burst of spice. We recommend The Edge in the original, mahogany-hued Corojo wrapper varietal with its hearty core of Nicaraguan long-fillers and rich, peppery profile of cayenne, leather and coffee beans. 

The full-bodied punch The Edge can pack is best chased back with a shot or two of Wild Turkey 101. The iconic, easy-to-reach bourbon is perfectly matured in American White Oak barrels for a deep, earthy char. A well rounded blast of vanilla, caramel, honey and tobacco are guaranteed to ring your bell and wake you up with a spicy Rocky Patel The Edge wafting from your mouth.


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#11 - Romeo y Julieta 1875 & Buffalo Trace

An entirely well-known Cuban-heritage brand embodies its historic reputation with Romeo y Julieta 1875, a tasteful blend of Dominican long-fillers beneath a gingerbread-hued Indonesian wrapper leaf. The mild to medium-bodied recipe presents notes of toasted nuts, peppers, and coffee beans throughout a perfectly balanced finish at an amazing value.

Buffalo Trace is a magnificent companion with an equally revered appreciation. Its deep amber appearance reveals a textured aroma comprised of vanilla, mint, and molasses. Toffee, candied fruit and brown sugar notes receive a bit of welcome contrast from the cigar’s woody spices. Hints of dark fruit and anise emerge in a splendid marriage you’re guaranteed to discover for an accessible price in a number of places.


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#12 - Punch & Jim Beam

We’ve been saying it for decades. Nothing tastes better than a ‘Punch’ in the mouth… except, perhaps, a Punch with a striking sip of Jim Beam. For the best match-up with bourbon, put a medium-bodied Punch Maduro on your radar with its toothy Connecticut Broadleaf wrapper. A hearty profile of peppers, molasses, and cedar readily characterizes the complex interior of Dominican, Nicaraguan, and Honduran tobaccos in Punch, and for a great price.

Among the best-known bourbons period, Jim Beam keeps up with a Punch Maduro in spades. Oaky notes of vanilla, caramel and toffee shoot through the olfactory senses as well as your taste buds with a sense of purpose and a touch of sweetness. Four years of aging in new charred oak barrels deserves to be savored with a proper smoke. One good icon deserves another, so indulge your inner lumberjack with this staunch pair.

It doesn’t matter if you’re out and about cigar-bar-hopping, or you’re camped out in the man cave watching a game with your pals, we guarantee our recommendations offer enough ammunition to stimulate your sweet tooth for bourbon and cigars all night long. Fire up with a pour that sounds like a fantasy come true for your senses. 


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Other Liquor & Cigar Pairings

Of course, when the bottle is gone, there are plenty of other spirits to pair with cigars. If you’re a straight-up whiskey and cigar connoisseur, we’ve got plenty of scotch and cigar pairings and rye and cigar pairings to whet your appetite. Cigars and rum taste amazing together too. Stock your bar at home with the best spirits to drink with cigars.

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