Unfortunately the Flor de las Antillas is actually one I forgot that I not only have, but have smoked several of. It's actually my friend's go-to cigar. Just as an aside, the last time we did this he asked the guy at the store for a suggestion similar to the FdlA and the guy gave him the Epernay. The Don Carlos is a good suggestion. I might try to steer us both towards the AF section because of the impending trip.
I tend to try to stay away from beers that are too hoppy when smoking cigars, too. I've been on a stout and porter kick lately, but there are some winter ales that I really like. I think I've only ever smoked one cigar when I wasn't drinking some sort of alcohol and that was the Virtue and I had it with coffee. I think that pairing was as least as good as any beer, whisky or wine pairing I've ever had, but I also usually smoke at night and don't want the caffeine (and do want the alcohol).
I can also guarantee that I won't take this too seriously. I smoke to relax and obsessing over the details is the opposite of relaxing for me. A "less than optimal" pairing has never upset me. I just thought it would be fun to get some suggestions.
I appreciate all of the suggestions! I'll be sure to update with what we both ended up with.