Welcome and good luck. Makers Mark does a bourbon infused cigar and several lower end makers do chocolate such as Hugo Caesar. I am not aware of a cigar that mixes both. I would recommend picking up a CAO flavours sampler which most of the major internet cigar retailers offer for between 15 and 20 bucks. Most folks around here do not go for the flavors- myself included. I will admit that is how I started though and going with Cojimar sugar dipped or the CAO option is a step-up from anything you will find in a gas station. Two of the cigars in the CAO flavours sampler almost fit your bill:
CAO MOONTRANCE is an intricate blend of natural exotic fruit and bourbon vanilla extracts. Bourbon vanilla, a type of vanilla bean renowned for its caramel-like sweetness is married with ripe George peach nectar and then mixed with other organic fruits. A splash of white honey from Hawaii is added for a tropical essence. An African Cameroon wrapper caps this striking tobacco blend.
CAO EILEEN’S DREAM is named after the owner of C.A.O.’s daughter, Eileen. This cigar has the flavor of white chocolate truffles and Irish cream.
Again, good luck. More people could use friends like you who go out of their way to bring them happiness.
Mama said a lot of things and be thankful was the one she never minded saying twice
--Drive-By Truckers
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