Five Cigars and their Perfect Bourbon Matches

Medley’s Private Stock 10 Year, Blanton's, Jefferson’s Very Small Batch, Noah’s Mill, and Woodford Reserve Double Oaked

Blanton's Single Barrel Bourbon. Photo Credit Victor Sizemore.
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Tatuaje TAA 2015

  • Strength: Medium-Full
  • Shape: Toro 5 5/8” x 54
  • Wrapper: Connecticut Broadleaf
  • Origin: Nicaragua
  • Price: $11
  • Pairs with: Medley’s Private Stock 10 Year

This boxed pressed beauty has a rich, textured, chocolate colored wrapper. Although sweet to the nose the finish has a soft bitterness and white pepper spice, which pairs well with Medley’s Private Stock 10 year Bourbon. The high rye Bourbon comes in at 90 proof and is easy to sip, yet has the spice to stand up to this annual Tobacconists Association of America cigar.

Oliva Serie G

  • Strength: Medium
  • Shape: Belicoso 5” x 52
  • Wrapper: Cameroon
  • Origin: Nicaragua
  • Price: $6
  • Pairs with: Blanton’s

The elegant sweetness of Olivia Serie G goes hand in hand with the burnt caramel flavor of Blanton’s Bourbon. These two brands were meant for one another and are as consistent as Nicaraguan long-leaf.

Arturo Fuente Hemingway Short Story

  • Strength: Medium
  • Shape: Perfecto (4″ x 49)
  • Wrapper: Cameroon
  • Origin: Dominican Republic
  • Price: $6
  • Pairs with: Jefferson’s Very Small Batch

These two make a historic pairing, just like the name sakes their brands are dedicated to. Both are unpretentious and well balanced with spicy and sweet notes, that compliment each other very well.

Long Live the King – My Style Is Jalapeno

  • Strength: Medium-Full
  • Shape: Lancero 7 1/4 x 40
  • Wrapper: Dominican Corojo
  • Origin: Nicaragua
  • Price: $11
  • Pairs with: Noah’s Mill

This is a beautifully crafted cigar, as is the entire Caldwell Cigar line up. Classic notes of cedar and mocha come to mind during this smoke. It stands up well against the bold flavor and high proof of Noah’s Mill Bourbon.

Montecristo White Vintage Connecticut No. 3

  • Strength: Mild – Medium
  • Shape: Corona 5.5 x 44
  • Wrapper:Connecticut Shade
  • Origin: Dominican Republic
  • Price: $10
  • Pairs with: Woodford Reserve Double Oaked

Cigars are like Bourbon or anything else, it’s personal tastes and style. It’s hard to find a single cigar that fits everyone, but this Montecrsito White Vintage No. 3 comes close. Very mild and smooth but packed with flavor that any smoker will enjoy. It pairs well with the baking spice notes of Woodford Reserve Double Oaked.