The last cigar I smoked (on Sunday, a nice pretty full-bodied Gurkha G5 Avenger), I had with a glass of red wine (don't laugh, it's called 'Menage a Trois' and it's a decent blend I picked up for $10/bottle).
While the wine is decent and certainly drinkable and at a great price, it's not exceptional (obviously with that price, it's more of a daily drinker/table wine).
I've usually had a cocktail or a glass of cognac, whiskey or a nice tequiia with my cigars and this was, I think, the first time I paired one with a red wine and I was a little apprehensive.
I FREAKING loved it. I'm not sure what took my so long to try it. And I'm not sure why or how, but the cigar made the wine taste (for me anyway) like a heavy, delicious & silky $50 Amarone or something of the like.
You know what else I did (and I'm not quite sure why maybe for the special effect), I even blew some of my smoke into the glass to watch it hang in there and then I blew it out. The combined aroma of wine & cigar was AWESOME.
I'm a buyer. Size.