8 Best Cigar and Bourbon Pairings to Elevate Your Experience

When we think of classic cigar pairings, bourbon is usually one of the first that comes to mind. It harks back to another era of gunslingers in the Wild West. Known as an enduring symbol of craftsmanship and tradition. It continues to be a go-to cigar pairing today.

Bourbon is often chosen for business meetings and marking milestones. But you don’t need a fancy occasion to open a bottle and settle down with your favorite cigar. You just need a quiet environment where you can relax and enjoy the nuances of each draw and every sip.

Below, we take a look at some of the best cigars to pair with bourbon. We examine them each side by side, unpacking what makes them so special.

Why are Cigars and Bourbon a Good Pairing?

Before we dive straight in, let's briefly cover what makes cigars and bourbon such a good pairing. Apart from the long history attached to this duo, they share similar flavor depths. 

Both cigar and bourbon are considered high in sensory value. They're known for incredibly layered profiles. 

That’s why it’s best to keep things simple when pairing these two together. Keep your bourbon at room temperature, and alternate between sips and puffs. Bourbon and cigars work best together when similar strengths are chosen. For example, softer, wheat blends work well with creamy cigars. More oaky varieties, on the other hand, pair nicely with full-bodied smokes.

Cohiba and Woodford Reserve

Perfect if you’re looking for an interesting blend that’s full of indulgence. Woodford Reserve is well-known in the bourbon industry. It has thirteen different gold medals, boasting a rich history in the Kentucky bourbon industry.

Cohiba Exquisitos is known for its spice, salted caramel, graham cracker, wood, cocoa bits, straw, and leather. These round out a smooth, medium-to-full-bodied smoke.

The Woodford reserve has a natural sweetness that works well in comparison. It’s packed with aromas of vanilla, caramel, cherry, and cedar. This helps bring out the sweeter elements of the cigar without overpowering it.

Montecristo and Basil Hayden's

If you’re a coffee-lover, we’d definitely recommend trying out this pairing. Montecristo cigars are known for their cashew, coffee, and creamy notes. They come with just the lightest hint of spice. An overall mild blend, this is a good pairing for cigar novices.

Basil Hayden’s complements Montecristo. It mixes together honey, pepper, and soft caramel with a creamy finish. It’s a light-bodied liquor with a gentle, highly approachable base.

Romeo y Julieta and Buffalo Trace

If you’re on the hunt for a highly approachable pairing, we’d recommend this one. Romeo y Julieta cigars are known for their distinctive body and taste. They come with a wide range of medium-bodied notes. Some of these include floral, roasted almonds, wild berry, and coffee. There are even notes of baking spice, among others.

Buffalo Trace Bourbon is a solid match for this cigar. It comes with a blend of caramel, vanilla, and light spice. This brings out similar notes in the Romeo y Julieta. The subtle spice in the Buffalo Trace is noticeable. But it doesn’t overpower the nuances of the cigar.

H.Upmann and Maker’s Mark

Another Kentucky bourbon, Maker’s Mark, has a unique flavor blend. Alongside strong notes of vanilla, caramel, and toasted oak, it also has a fruity cherry twist. This pairs great with H.Upmann, a cigar known for its cocoa, spice, and nut notes.

Maker’s Mark helps enhance the slightly nutty undertones beautifully. They’re one of the most well-balanced pairings on the list. Ideal for smokers looking for an easy, relaxed pairing experience.

Trinidad and Longbranch

Trinidad cigars are rich, medium to full bodied cigars. They’re highly regarded in Cuba, with an aromatic, complex blend. They blend together tea, oak, citrus, smoke, and earth with a slightly floral note.

Longbranch bourbon is equally complex. It’s ‘refined using charcoal from both Kentucky white oak and Texan mesquite.’ It’s incredibly full-bodied and smoky. This bourbon goes down well drunk neat. The smokiness of the Trinidad pairs beautifully with the earthy smoke of the bourbon.

Punch and Jim Beam

Another highly drinkable combo, Punch and Jim Beam make an excellent pairing. A classic bourbon, Jim Beam boasts sweet caramel and vanilla. It also displays a woody grain and oak flavor, adding to its complexity.

The sweetness from the caramel really helps bring out the earthy notes of the Punch. The smooth finish of the bourbon also helps soften the cigars’ peppery notes. This medium-bodied smoke makes a great pairing for more casual, relaxed evenings.

Juan Lopez and Woodford Reserve Double Oaked

Juan Lopez is one of the earthiest, woodiest cigars on our list. It’s medium to full-bodied, creating a rich and silky smoke. Juan Lopez cigars are packed with tobacco from the Vuelta Abajo region. This is widely considered the best cigar tobacco growing region on the planet.

This cigar pairs best with Woodford Reserve Double Oaked. This bourbon is incredibly oaky itself, but also has notes of caramel and vanilla. The sweetness of these flavors serve as a delicious contrast. The warm, oaky notes make this pairing perfect for cold winter nights.

Partagás and Wild Turkey Bourbon

If you’re looking for something a little different, we’d recommend this pairing. Partagás are known for being full-bodied and packed full of flavor. They have a highly distinctive earthy quality enhanced with a spicy undertone. 

The flavor of the cigar is exceptional when paired with Wild Turkey Bourbon. The latter is known for its high rye content and intense spice levels. When paired together, they emulate a mouth-watering warmth. Great for enjoying after a meal.

Pairing Bourbon with Different Types of Cigars

There’s an art to finding the perfect cigar and bourbon pairing. Thankfully, once you have the know-how, you can easily start making your own. There are a few simple rules to follow, as discussed below.

Mild Cigars: If you’re a lover of mild cigars, it’s best to pair these with soft bourbons. Bourbon is a naturally dark, rich spirit, so it’s important to do some research. Look for Kentucky bourbons like the Woodford Reserve mentioned above. These typically feature lighter flavors like vanilla and caramel.

Medium Cigars: For medium cigars, you have some more room for maneuver. They often have a balance of sweet, and more woody notes. We’d recommend choosing bourbons that hit similarly on the palate. Opt for those with a blend of lighter sugary notes and darker, oaky notes.

Full-Bodied Cigars: If you’re a fan of full-bodied cigars, it’s good to choose equally bold bourbons. Spicy, earthy cigars need bourbons with minimal dilution. Complex, rich bourbons help bring out the leather and dark coco notes in full-bodied cigars.

Pick Your Pairings

Cuban cigars and bourbon have been a favorite for centuries. It’s not hard to see why. With so many unique flavor combinations out there, there’s something for everyone. It’s no wonder this pairing is so highly regarded. 

Now that you know all the ins and outs of pairing Cuban cigars, it’s time to buy some smokes. Here at Swiss Cuban Cigars, we sell a wide selection of premium, authentic Cuban cigars. Browse today to start your journey.