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I may have found the best pairing ever...

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I'm a scotch, whiskey, bourbon guy. Mostly scotch though. Balvenie, Dalmore, Glenmorangie are my go to 3 brands. But I also enjoy Glenlivet, Highland Park, Johnnie Blue, Macallan, Aberfeldy... I second the less peaty the better though. Not only do they not pair well, I personally can't stand Islay or Lowland peat bombs. For the intro drinker, I'd suggest something like Glenmorangie Original. It's my favorite everyday drinker, subtle, light, but still complex. Compliments Connecticut hard wrapped cigars well with the lighter, younger coconut, vanilla and slight banana flavors. For the maduro fan, start diving into things aged for 12-18yrs and will some maturation in sherry or oloroso casks.

Personally right now I'm enjoying a glass of Dalmore 12yr, which is aged in half in American white oak bourbon barrels and half in Oloroso sherry casks. Somewhat dark and nutty, while still youthful and smooth with plenty of vanilla and caramel notes, it is pairing quite nicely with my Cabiguan Maduro cigar before bed.

That said too, when I don't have a spirit with my cigar, I too enjoy a cup of coffee, or on those nice summer/spring afternoons, I also like a glass of black iced tea.
 

ciggy

"TommyBoy"
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I am with a few fellas here and make my cigar the main focal point without pairing. However the question at hand is about pairing so with that in mind I will say that every once in awhile I find a good Rum (Zaya or Zacappa), Smooth scotch whiskey, or coffee can inhance a cigars taste. I'm a casual drinker so I find a diet coke works most of the time for me but that's just to wet my mouth and not ruin the overall body of the cigar.
 

JDog

BoM Nov '12 & May '13
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I actually will occasionally smoke something with rum, Zaya. But it's so sweet I like to put a few ice cubes in the glass.

If I do smoke something with scotch, I prefer something light (not peaty), like Glenmorangie Original. I drink that neat.

I nearly always drink coffee... throughout the day... I've been known to have a cigar with a cup.
 
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