129 – Bourbon Trail meets Tobacco Road, Bourbon and Cigar Pairings with Jake’s Cigar Bar

Enjoying a glass of bourbon while smoking a cigar seems like an average Friday night to some people. However, pairing a bourbon and cigar can be more complicated than you think. We sit down with Jake Glancy and Jeremy Kendrick of Jake’s Cigar Bar to get a complete cigar 101 lesson on everything from cuts, types, leaf varieties, and more to understand how the unique flavor of a cigar will compliment different types of bourbon. You will want to rush outside and smoke a cigar after listening to this one!

Show Notes:

  • Let’s start from the beginning and talk about the types of cuts
  • How do you pick the ring gauge or size of cigars?
  • Talk about the wrappers and what flavors each type release
  • What’s the difference between tobacco in Nicaragua and Honduras versus in Kentucky?
  • Talk about hand-rolled versus machine-rolled.
  • Bourbon drinkers have a progression from mixing to neat, what about cigar smokers?
  • What do you mean by tasting a cigar by “thirds”?
  • It’s moving from cigars and scotch to cigars and bourbon. What’s the initiative?
  • Describe the different shapes of cigars
  • When you’re smoking a cigar do your taste buds or receptors change rather than drinking bourbon alone?
  • What’s the sweet spot for the third in your opinion?
  • I’m going to throw some bourbons at you and you tell me what cigars would pair well.
  • Talk about higher in proof bourbons like Stagg Jr and barrel proof bourbons and the cigars that pair well
  • It seems like Four Roses pairs well with any cigar
  • Talk about barrel aged cigars
  • What about something super light like 80 proof Basil Hayden
  • Rye whiskey is growing in popularity. How does rye whiskey stand up in cigar pairing?
  • How about something that’s super oaky like Elijah Craig 23?
  • How about finished bourbons like Angel’s Envy port finished bourbon?
  • The craft market is booming but what do you pair with something that has a grain forward flavor?
  • Talk about the Van Winkle Cigars. Are they good or are they hype?
  • I see a lot more Barrel aged cigars on the market and I am curious for recommendations and also some info on the technique and how it imparts the flavor from the barrel to the tobacco.
  • Are Cubans really that much better?
  • Get 15% off at Jake’s by mentioning you heard about them on Bourbon Pursuit!

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