Bourbon & Cigars: Tips For Pairing Two Luxurious Worlds

Since 2002, Windy City Cigars has been offering the convenience of buying cigars online directly through our site. We’ve now become the biggest online cigar retailer, and we’re very proud of that. You’ll find the best prices, the best selection, and always-in-stock favorites and accessories on our site. Many customers come into our store or call us and ask us to recommend cigar pairings for Bourbon. We’ve got some suggestions for you!

People spend years looking for the perfect Bourbon and cigar combination. We suggest matching cigars and bourbons that have similar body strengths.

Four Roses Bourbon: This is one of the lightest bourbons with honey, anise, walnut, and caramel notes. This pairs well with light-bodied cigars like the Macanudo Prince Phillip.

Evan William’s Single Barrel: This is a light-to-medium-bodied bourbon that mixes oranges, vanilla, and anise flavors with a sweet caramel nose and a long finish. This pairs well with Macanudo Prince Phillip cigars as it draws out the creamy, spicy sweetness. It pairs even better with Padrón 1964 Anniversary Series Exclusivo.

Booker’s: This orange, vanilla, leather, pecan, honey, and cherry bourbon could be called a high-octane bourbon. The 125-proof bourbon pairs well with the Montecristo #2 cigars as it pulls flavors from the cigar that aren’t apparent before.

Pappy Van Winkle’s Family Reserve: This hard-to-find; full-bodied Bourbon gives a woody, smoky, almond, and cherry taste alluring to some but is considered an acquired taste. It matches well with the Montecristo #2 where it finds cocoa and cedar qualities downplayed in the cigar. The Arturo Fuente Opus X cigars also pair quite well.