Favorite pairings

I had to quit cigars because they have adversely affected my health. If you smoke cigars, watch out. Smoke them sparingly. You're rolling the dice. I never even smoked cigars that often: about once per month per month on average when I was smoking, and that's not counting long periods when I didn't smoke at all. This said, I love cigars even though I can't smoke them any longer. I loved smoking Don Pepin Garcia Blues and drinking Caol Ila mixed with Cruz Silver tequila. Talisker also mixes well with creamy smooth tequilas making them somewhat mescal-ish. Of course, Longrow Gaja wood is just fantastic with a cigar all by itself. So is Longrow CV. I also like a good rum with cigars. I had a girlfriend in Seattle that had family in Canada. We used to drink Havana rum and smoke Cuban cigars. It's hard to beat that combination with anything anywhere. It's a luxury I lost when we broke up. Oh well. Despite her family's superb taste in many things, she had the worst breast implants I've ever known. Hard as rocks. Hey, I'm just sayin'.

Glenfarclas 105 goes great with practically any desert. In fact, it's kind of a desert in and of itself. If you can't get that, snag a bottle of the Macallan Cask Strength. It's already gone in Europe for the most part but still available in the USA. It's also a terrific after dinner scotch that pairs wonderfully with chocolate, caramel, toffee, vanilla ice cream, etc.

Of course there was one month a few summers ago when I smoked about fifteen cigars on vacation.

I find a good milk chocolate, or, interestingly, an aero bar, goes nicely with a sherry-matured single malt. I have an appreciation for Trader Joe's milk chocolate, though I don't often get to shop there, living in the 51st state.

They also make chocolate covered chocolate nibs. These go well with most whiskies, I find, even some of the really smoky ones.

I really haven't paired much else directly, though when the Whisky club meets and we are planning an Islay dram, we try to have smoked salmon available.

I have heard that Bruichladdich "the laddie classic" paired well with fresh oysters. But I haven't tried that.

I'm in principle against eating anything with my whisky - I feel it corrupts what the whisky intended to be. However, I don't let many people know that in case they think I'm some sort of whisky elitist - which I'm not!

While the usual combinations (chocolate, java, cigar, etc) are quite common I think the best way to try and pair anything is to think like a chef.

Thus, a single malt like Glenfiddich 18 (chocolate, candied orange, burnt citrus, almonds) would go well with a dark (slightly bitter) chocolate dessert. Keeping the chocolate bitter will make the malt sweeter and more palatable. The other way around will make the malt bitter - which is not nice.

Bourbons are known to go well with a good steak. In fact I soak my steaks in (cheap!) bourbon for that little twist. You can even make a nice bourbon reduction to pour over your smoky grilled meat.

The Ardbeg 10 (peaty, sooty, ashy, lemony) could go very well with sausage on grill.

I would try and find the most dominant flavor profile of an expression and see what actual food it complements.

Sherry-matured malts with dark chocolate (Lindt dark chocolate with chili or sea salt is really nice). My personal favourites so far have been Compass Box Spice Tree with a ginger-pear upside down cake (the spices complemented each other very nice), the Clynelish 1993/2010 Distiller's Edition with fresh dates wrapped with candied apple-wood smoked bacon, or anything peated with a nice sharp cheddar or a strong blue cheese.

I'm among the chocolate with sherried whiskies crowd, and I also like chocolate with a smoky whisky.

The coup de grce, though, is Roquefort cheese with a smoke bomb: Alligator, PC10, cask strength Kilchoman or the like.

@rigmorole I don't smoke cigars but thanks for the pairings. These all sound excellent thank you all for contributing.

Dark chocolate & peaty whisky is the best (only) combo I ever recommend.

The best combo that I can REMEMBER, though, was Caol Ila with a full Scottish breakfast including smoked fish at a B&B on Islay. Do I feel like having that again, right now--or ever? No. But do I wish I was back there again? YES!