2016 CA Report: 17 Top Whiskey and Cigar Pairings

2016 CA Report: 17 Top Whiskey and Cigar Pairings

17 Whiskey and Cigar Pairings in Honor of St. Patrick’s Day!

By Jonathan Detore

March is my favorite month of the year. It’s not only the month in which we celebrate St. Patrick, but it’s also when we celebrate myself and the glorious day I was brought into this world. I consider it a coincidence that both days fall on the 17th of the month, and a double coincidence that ever since my 21st birthday the actual events of the day seem to slip my memory. Maybe I just don’t want to remember another day in which I grow older, or maybe it’s because of all the beer and whiskey and cigar overindulgences. It’s a mystery that, I’m afraid to say, will never be solved. But since we’re on the subject of drinking, I know a lot of you are celebrating with a whiskey and cigar matchup of your own this year – which is why I’ve taken it upon myself to give you my list of must-try pairings for the St. Patrick’s Day season. Yes, season – because it can’t be contained to just one day.

The inspiration behind my suggestions come from a little tradition of mine called “The 31 Days of Whiskey,” where I enjoy a drink of whiskey every day for the entire month. It just so happens that I also work at a cigar company that has a bar attached to it so I can have a smoke with my daily libation. It goes without saying that a few years of doing this has had me stumble (ha!) upon a couple of amazing pairings that I feel are astounding and would recommend to my friends. And seeing as all cigar smokers are bonded by a smoky brotherhood, you are all my friends and thus privy to my recommendations.

Rest assured that these are all actual pairings that I have tried mainly at Leaf Cigar Bar and Restaurant here at work or at my home, with some of the rarer pairings having been sampled at higher end cigar lounges in New York City or Philadelphia. Also keep in mind that, just like St. Patrick and corned beef & cabbage, not all of the whiskey pairings are of the Irish variety. So kick back and take notes on what is I think is worth trying with these 17 whiskey and cigar pairings!


CLE Plus 2015 Robusto and Jameson Original

buy CLE Plus 2015 cigar pairingsThe CLE Plus 2015 is a newer offering by Christian Eiroa and a rehash of the original CLE which was a powerhouse of blast-your-face-off strength and flavor. The 2015 version is lighter and more floral than its big brother, which means I had to pair it with something similar. Jameson Original was a no brainer, with a light body and similar notes of vanilla and floral aspects that greatly complement each other and help draw out each other’s hidden flavors. It’s flavorful and light the whole way through to help kick off the St. Patrick’s Day holiday.


A Flores Gran Reserva Half Corona with Wild Turkey 101

buy A Flores Gran Reserva cigar pairingsBlended to honor Abe Flores, this is one of my favorite cigars of all time. It may be small, but it’s big on burn and flavor. Word to the wise: remove the cedar sleeve from around the cigar, and use that to light it. When you do, you’ll be rewarded with pepper up front and a woody sweetness to follow, along with a dipping and diving of complementary flavors. A great pairing to this is one of my all-time favorite American Whiskeys, Wild Turkey 101. The 9 year aged gem has a heck of a bite that matches the initial spice of the cigar, but then settles for an oaky and candy-like sweet aftertaste. It’s a strong one to be sure, but one you’ll keep going back for.


Arturo Fuente Hemingway Short Story with Blanton’s Special Reserve

buy Fuente Hemingway Short Story cigar pairingsArturo Fuente Hemingway Short Story cigars are some of the best lounging cigars on the market. These small 45 minute smokes will deliver wave after wave of soothing sweet cedar and very mild pepper all the way through. It may not be backed with a lot of complexity, but it’ll have you salivating for more after every puff. A superb pairing for this is the subtle Blanton’s Special Reserve. Never overpowering or lingering, this American Bourbon relies on hints of light vanilla, very slight spice, and a woodsy/almost grassy flavor that marries well with the naturally woody and savory Cameroon wrapper of the Short Story. It’s not a whiskey and cigar pairing that will promise intense flavor, but rather it will deliver a savory cooperation to completely round each other out.


Padron 1964 Anniversary Maduro Pyramide and Redbreast 15 Year

buy Padron1964 Anniversary cigar pairingsI first tried the well-aged Padron 1964 Anniversary Maduro Pyramide courtesy of my brother for my 21st birthday. Fast forward 5 years and I still come back to this timeless cigar. Luckily I was able to try it again with a recommended pairing of Redbreast 15 Year Old Single Pot Still Irish whiskey. The pairing completely blew me away, and I will certainly say this is perhaps my favorite in this list. The rich decadence and smooth creamy back end of this cigar is enhanced by the deep warm flavors of the Redbreast, while also receiving further complexity from a sweet caramel/toffee and slight zest on the back end of this astounding whiskey.


Davidoff Escurio Gran Toro with Balvenie Single Barrel 15 Year Old

buy Davidoff Escurio cigar pairingsDavidoff Escurio is refined, sweet, creamy, leathery, and spicy; it essentially runs the gamut of flavor and mind-blowingly epic complexity. That’s why it’s a no-brainer to match it with a favorite Scotch whisky of mine, the Balvenie Single Barrel 15 Year Old. Its delicate honey/fruity sweetness with a slight barnyard note is followed by a noticeable spice or “bite” that perfectly matches the Escurio’s dramatic rise and fall of a similar wide variety of complex flavors. Notice I spelled “whisky” without the “E” in this section. As a point of interest, it is mainly Ireland and the United States manufacturers who use the spelling “whiskey” while a majority of the world discards the “E.” Even more interesting, the legal classification of this libation in the U.S. is spelled “whisky,” yet most U.S. manufacturers include the “E.”


Rocky Patel 20th Anniversary Toro with Midleton Barry Crockett Legacy

buy Rocky Patel 20th Anniversary cigar pairingsThe Rocky Patel 20th Anniversary is on my list of favorite cigars, with a purchase of a 5-pack being a no brainer the minute I run out of them in my humidor. So I was extremely happy when I found a savory pairing for such an exquisite cigar. The dominant rich coffee, cocoa, and chocolates in the cigar mellow out and receive a caramelized topping when married with the velvety smooth flavor of Midleton Barry Crockett Legacy, with additional notes of cinnamon and a small spice adding to the delight. This is more of a contrasting whiskey and cigar pairing since the flavors don’t exactly match each other, but the 1-off flavors swirl together to create a flavor that is completely new and delectably different.


Undercrown Shade Robusto and Tullamore D.E.W. 12 Year Old Special Reserve Irish Whiskey

buy Undercrown Shade cigar pairingsThe Undercrown line may have dipped into the medium body range with the Undercrown Shade, but as it toned down in strength, Drew Estate amped up with incredible flavor. A solid yet meticulously refined citrus flavor mixes with a creamy nuttiness and a mild spice which pairs perfectly with Tullamore D.E.W. 12 Year Old Special Reserve Irish whiskey. The creamy, lightly spiced citrus, and sweet oak from its time in bourbon and sherry casks match the natural flavors of the Drew Estate Undercrown Shade for a pairing that is sure to be finish off this St. Patrick’s Day weekend properly.


Java Mint Robusto and Irish Coffee including Paddy’s Irish Whiskey

buy Java Mint cigar pairingsI’m cheating by adding Irish coffee, but it’s a traditional drink for St. Patrick’s Day morning (bonus points if you say, “or any morning”). I usually mix my Irish coffee using Paddy’s Irish whiskey. First produced in 1779, Paddy’s is unassuming, yet gets the job done with a biting spice that works through the Baileys, coffee, whipped cream, and Crème de Menthe to really wake you up right. Light up a minty, chocolaty, and sweet Java Mint, and you have a whiskey and cigar pairing that was truly made for each other.


Illusione 888 Candela with Jim Beam Signature Craft 12 Year Old

buy Illusione 888 Candela cigar pairingsIllusione 888 Candela cigars blow you right into the past with a traditional Candela wrapper that was widely used back before Frankie Valli and the Four Seasons were a thing. With medium bodied woodiness mixed with a solid earthy characteristic, I like to pair this green delight with Jim Beam Signature 12 Year Old American Whiskey. Its time aging brings out a fantastic oaky spice that blends with the 888’s natural flavors, while also laying down some extra sweetness to round out the smoke and bring out an almost sweet coffee flavor.


Perdomo Craft Series Amber Epicure Sun Grown and Bushmills 21 Year Single Malt Irish Whiskey

buy Perdomo Craft Series cigar pairingsPerdomo Craft Series Amber Epicure Sun Grown cigars are a recent offering by Nick Perdomo, and a recent favorite of mine, specifically blended to pair with heavier malt-forward American style Ales and even some IPAs. But that doesn’t mean you are forbidden from pairing this cigar with anything other than beer. Case in point: Bushmills 21 Year Single Malt Irish whiskey. The heavy yet semi-sweet malt and dried fruit notes of the cigar match up well with the almost toffee, chewy malt, and slightly fruity back end flavors of the Bushmills with a slight bite to keep your attention.


My Father Le Bijou 1922 Torpedo and Pappy Van Winkle’s Family Reserve 23 Year Old

buy My Father Le Bijou 1922 cigar pairingsA cigar like the #1 Rated My Father Le Bijou 1922 Torpedo has to be paired alongside some of the best whiskies in the world, which is why I had to give it a shot with Pappy Van Winkle. The Le Bijou has a wide array of complex flavors including wood, chocolate, coffee, and leather, with a mild spice consistent throughout the entire smoke. With all this going on, the Pappy Van Winkle’s Family Reserve 23 Year Old still manages to marry with the cigar’s decadent flavors with a matching mild coffee and creaminess, and a similar subtle spicy finish, while still offering oaky and nutty components that stand on its own. If you have the means to experience this whiskey and cigar pairing once, it is well worth it.


La Gloria Cubana Serie RF No. 00 with Bulleit Bourbon

buy La Gloria Cubana Serie R F cigar pairings If we were to describe the La Gloria Cubana Serie RF and Bulleit Bourbon, we would almost be forced to use the same adjectives and flavor notes for both. Spicy up front with a creamy, sweet, and smooth tail end. But mixed together, the spice recedes quite a bit to open up into an exquisite coating of sweet oak, a rich earthiness, and a hint of creamy toffee on your palate, while still maintaining a rather biting spice that is wildly enjoyable.


Dram Cask #3 Toro and Angel’s Envy

buy Dram Cask cigar pairingsDram Cask #3 cigars are a relatively spicy offering among the entire line of Dram cigars, so a spicy pairing only makes sense to match it with it. What better pairing is there than Angel’s Envy Kentucky Straight Bourbon finished in port wine barrels? Both have a good deal of spice, but when mixed together with the taste of vanilla and nuts, a honey and fruity-like sweetness cuts the spice for a complex, chewy, and relaxing smoke. Neither overpowers the other yet both perfectly complement one another by cutting down each other’s spice, and bringing out the subtle flavors in both the cigar and bourbon.


Black Belt Buckle Corona Gorda and Jack Daniel’s

buy Four Kicks Black Belt Buckle cigar pairingsBlack Belt Buckle kicks the flavor up to 11 with earthy sweetness and charred woody notes, courtesy of a mix of heavy Nicaraguan longfillers and a naturally toothy Connecticut Broadleaf Sun Grown Maduro wrapper. This salt-of-the-earth style smoke, through its rugged appearance and bold flavors, needs a whiskey that does it equal justice, which is why I’m breaking out some Jack Daniel’s Old No. 7. In a pairing that just screams “Hold my beer and watch this,” this anything-but-hoity-toity matchup blends the slight sweetness found in each along with a common woody trait which is brought on in the Jack Daniel’s through its time left to age.


Aging Room Quattro F55 Espressivo with Bernheim Original

buy Aging Room Quattro F55 cigar pairingsA cigar that starts as full-powered as the Aging Room Quattro F55 Espressivo needs a whiskey that hits just as hard and fast. Luckily, through my St. Patrick’s Day adventures, I think I’ve landed on a good pairing for it. The F55 opens with a buttery sweetness that lingers on the palate under prominent spice, with some chocolate and nutty notes settling in further along the smoke. Bernheim Original adds to the creamy buttered theme, but adds in a dry toasted note and mild spicy bite that can be attributed to a shorter aging period. This combo actually cuts into the F55’s spice to allow the underlying flavors of the cigar to come more to the forefront, creating a deliciously sweet and tantalizing smoke.


Camacho American Barrel Aged Robusto and Knappogue Castle 12 Year Old Single Malt Irish Whiskey

buy Camacho American Barrel Aged cigar pairings Trying to find an affordable world-class whiskey and cigar pairing is a fairly hard mountain to climb, yet here we are, standing at the peak of a shallow hill with Camacho American Barrel Aged in one hand, and Knappogue Castle 12 Year Old Single Malt Irish whiskey in the other. Aged for 12 years in bourbon casks, the malt and sweetness from the Knappogue marries well with the toasty bourbon flavors of the American Barrel Aged, which is also aged in bourbon barrels for a year after an initial 6 years of aging. The flavors infused in both the cigar and whiskey from their time barrel aging truly does wonders to round out this pairing and bring similar flavors to the table.


Montecristo Relentless No. 2 with Teeling Small Batch Irish Whiskey

buy Montecristo Relentless cigar pairingsThe Montecristo Relentless No. 2 is notorious for having a slight barnyard flavor, mixed around with some creaminess, nut, and a slight woody note, making this an incredible addition to the storied Montecristo brand. So a cigar this complex under such a well-known brand needs a whiskey that will simply blow this pairing into the stratosphere. Teeling Small Batch Irish Whiskey does the trick, with similar grassy qualities as the Relentless, along with vanilla, caramel, and bakers spice which was most likely picked up during its time maturing in rum casks.


Through my 31 Days of Whiskey I have been able to experiment over the past 3 years to find what works right for me. I’m positive that of the 17 listed above, you’re bound to enjoy a handful of them while others you may not be so fond of. This is simply because everyone’s palate differs. What works for me might not work for you. If I leave you with anything aside from the pairings I suggest, it’s that I hope you explore the pairing world to find what works best for you. Your favorite pairing may be a whiskey and cigar you may not even have thought of or maybe don’t even like individually! At the end of the day, it’s all about the journey to find what works for you. Until then, keep your glass to the rafters, and enjoy the rest of your St. Patrick’s Day weekend.


Jonathan DeTore

Jonathan DeTore

Copywriter at Cigar Advisor

My job here is pretty simple - I write stuff, I post stuff to Facebook, and I take it to the house consistently at the weekly slam drunk contest. I do it all while sipping on a fine glass of cognac at my desk (don’t tell my boss), and wearing cashmere slippers. Let’s just say "The Hef" has nothing on me.

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