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Well, I'm all about nostalgia. The fact that tobacco originated in the Caribbean and Central America primarily causes me to want to enjoy it with rum. I realize that the ancient Mayans were not drinking rum during their sikar, but it seems appropriate to me. I'm not too knowledgeable on rum, so I don't know what's good and not, but I have settled on Captain Morgan Private Stock. I feel like CMPS is a good balance between descent rum and not blowing my retirement savings on booze...

I also love bourbon. I don't know what it is about bourbon that's so attractive. Maybe it's Lexington. On a few occasions I've been fortunate to spend some time in Lexington around horses and bourbon. It's like an upper class who's down to earth, and I admire it. I've stood in Keenland with a glass of bourbon and a cigar and watched my horse run like the wind. It was enchanting. I can't imagine the experience without the horse, the cigar or the bourbon...

Wine is a no-brainer. Wine is just as amazing as cigars, and pairing the two together is bliss. I do worry about the two affecting each other's flavor, but it usually doesn't seem to be an issue. Wine, like cigars, are a true artistry. I can't imagine enjoying a cigar with white though. I think red is the way to go. Dark and deep...

I've actually started drinking more water while smoking cigars. Part of the reason is that I live in Arizona, and this time of year staying hydrated is a must. Also, I appreciate the cigar without always having the influence of alcohol. If I'm going to smoke an amazing cigar, I love a clear, hydrated mind to enjoy it with!

I rotate between those four...

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Try Bacardi 8 year old

Coffee is maybe my favorite cigar sidekick. But since I don't drink it after early afternoon, usually find myself on rum or bourbon with a nighttime smoke.

Haven't found anything in the "wine family" besides port and cognac that was worth a crap with stogies, but then I never liked conventional wines to begin with. YMMV.

My wife and I sat down last night with a couple cigars and a good deep bottle of red wine.  Not sure what it was, but it was good.  She was smoking a Short Story, which she didn't seem to like.  Eventually she abandoned me outside and retreated to the living room with the bottle while I finished my cigar.
Agreed, depends on the cigar...a stick that's truly a premium by your tastes is sometimes best to enjoy slugging water so you can enjoy the smoke simply for itself ....but, also agree many spirits make a great compliment to any number of cigars...though the stronger the drink on the palette, the less sense for the cigar itself...How often do I combine drink & cigars?...all of the time...and will admit that the the combination can make the nub of a grass cutter one of the best experiences you can have.  :)  Just my thoughts anyway...

My first choice will always be coffee, though like others have mentioned, I generally do not go this route in the afternoon.

My next favorites are port, scotch, and some really nice bourbon barrel aged stouts and porters make wonderful pairings too

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