When enjoying a fine cigar, there are three things you need to make your experience complete: a good smoke (that’s a given), a good drink, and good company. Well, we here at Cigars.com generally don’t like people, so we tend to focus more on the other two. One of the most traditional beverages to pair with your cigar is a fine whiskey (or “whisky” if you’re one of those guys). After much grueling research and dedicated work, we have come up with a list of our favorite cigar-and-whiskey pairings. 

Caldwell All Out Kings & Angel’s Envy Rye

This was the most recent pairing I did, mostly because this is the newest cigar on the list, the big, highly anticipated collaboration between Caldwell Cigars and Drew Estate. Although it was supposed to come out in November, Willy Herrera and Robert Caldwell love to torture me and made me wait (I wrote them a very nasty Facebook message and then they blocked me, but that’s neither here nor there). I smoked two of these cigars solo to get solid tasting patterns before I decided which whiskey to pick, and honestly, I knew after the first few puffs.

Angel’s Envy is one of America’s most popular bourbons, and one of the most critically acclaimed due to the company’s 200 years of whiskey-making tradition and its dedication to creating new and enticing blends.

Angel’s Envy Rye was a perfect matchup. First of all, it has a gorgeous reddish-amber color—and appearance plays a part in whiskey just like it does with cigars. This is a dry whiskey but it’s bursting with rich hints of oak and has a lingering sweetness toward the end. It pairs magnificently with the flavor profile of All Out Kings, which is rich with notes of nuts, wood, and sweetness. In fact, this combo was so good that I had to do it a few more times and then call an Uber.

A.J. Fernandez San Lotano Habano & Midleton Very Rare 2016

This pairing wasn’t exactly intentional. After work one evening, I went to my local spot and lit up a San Lotano that’s been sitting in my humidor for around a year (with a little age on these puppies, they really blossom). I was joined by a friend, who told me we had to try this Irish whiskey he’d heard so much about (he is one of those friends that doesn’t shut up so I said yes just to appease him). My Irish whiskey of choice has always been Jameson, but I figured what the hell? Little did I know that he had actually found something of value.

Midleton Very Rare is a yearly release of Irish whiskey almost as sought after as Pappy is by the bourbon crowd. What I found interesting was that it had a slight similarity to bourbon, which makes sense, as I was told that it’s aged for 20 years in American bourbon barrels. It is incredibly smooth at first, then begins to ramp up with complex notes of vanilla, sweetness, and an abundance of different spices. It has been named on several “best of” lists, and from what I have read has a dedicated following. After enjoying a glass or two, I can see why.

At first, the San Lotano has a bit of a chocolate note to it, which went pretty well with the vanilla sweetness of the whiskey. But it was the end of the cigar’s first third, where an array of spices comes into play, that really made this pairing a dream.

Montecristo White Series & Bushmills 21 Year

This pairing is based upon one word: smooth. Long hailed as such, the Montecristo White consists of a golden Ecuadorian Connecticut wrapper, and aged Dominican filler and binder. I won’t go into too much detail on the cigar because almost everyone reading this has probably smoked it before, but I’ll give you some quick notes: It’s undeniably smooth and creamy with heavy hints of nuts, sweet coffee, and cedar.

Now, I had the chance to pair it up with one of the smoothest Irish whiskeys I’ve had the pleasure of trying, Bushmills 21. It’s got a lot of complexity for an Irish whiskey, which is due to being aged not only in American Bourbon barrels but also Spanish sherry casks. So, it has some of the rich and spicy notes of a bourbon, with hints of sweetness from the sherry. Its age gives it a smoothness that may not common to other Irish whiskeys, but is a trait that has become expected with Bushmills.

Each sip starts out slightly smoky with notes of toffee before descending into hints of dark chocolate before a nice raisin-like ending with no after-burn or harshness apparent at all. Now, combine this with a cigar as smooth and creamy as the Montecristo White and that, my friends, is a good Tuesday night. Or was it a Wednesday? Can’t remember.

Herrera Esteli Norteño Corona Extra & The Balvenie 12 Year Doublewood

While the last pairing featured smooth and mellow, this one was much more focused on spice and pepper. First off, you have the Norteño by Willy Herrera; if there’s one man who knows how to make a top-of-the-line smoke with some great pepper and spice to it, it’s Willy. With its oily, San Andrés wrapper, this smoke is a combination of deep richness with notes of both black and white pepper, and a slight sweet spice as well.

Balvenie has always been one of my go-to Scotches. It is from Speyside, a region with a reputation for Scotches that are rich and sweet and that’s exactly what I get each time I fill up a glass (and, yes, I fill the glass!). It has hints of smoky pepper at the beginning and rich notes of fruit throughout, a great combination for a smooth single malt. The Scotch’s dried-fruit and pepper notes went hand in hand with the rich, sweet spice of the Norteño. Each puff was followed by the slightest sip, and it was almost like Balvenie literally made this whiskey to go with this cigar…one of the best whiskey pairings I’ve had in a while.

Rocky Patel Vintage 2003 Cameroon Toro & Michter’s Unblended American

I tend to stay away from Cameroons. It’s just a personal preference, I don’t hate them or think they have low quality (quite the opposite, actually; some Cameroon wrappers are the finest leaves I’ve ever seen on a cigar). However, I keep finding myself going back to this Rocky Patel Vintage 2003. This Toro just smokes so well and gives me my favorite characteristics of the Cameroon leaf while leaving out the deep, earthy notes that I usually find unpleasant.

I didn’t know what to match it with until someone suggested this classy American masterpiece. The first thing I noticed is that it wasn’t called “bourbon” but instead “American whiskey”—there was some rule that it has to be aged in a white oak cask, and it was aged in another cask; I didn’t really follow as I was more concerned with how it tasted…and, man, did it taste good!

It has a distinct sweetness to it, almost like butterscotch or some form of candy. It is also quite creamy with a nice sweet spice toward the end. As soon as I took my first sip, I knew it would match well with the Rocky Patel Vintage 2003, which is known for its delectable sweet spice as well as notes of nuts and sweet coffee. These two went back and forth in a matchup of sweetness that ended in a delicious draw. I highly suggest pairing this cigar with this whiskey, which definitely deserves more attention.