[D. Generate]

I've already posted about my lack of wine knowledge so this might be a dumb question. Do you pair cigars and wine? Is it possible?

Intuitively, I don't think it would work. I'm curious because tomorrow night I'll be adventuring into wines with dinner. I think my wife has earmarked either a Bordeaux, Rioja or Riberra del Duero for tomorrow. If that isn't specific enough or the right way to classify, I can look at the bottles.

I would like to smoke a cigar after dinner but would instinctively switch to whisky then.

I know some people like port and cigars, but I've only had a taste of port once a few years ago and I'm not sure if I like it. I do have a bottle of "Vintage Port" from 2001 that I got for Christmas from work. I can't remember the name although I can look that up if it's something that is recommended.

Should I pair a cigar with the wine? With the port? With whisky? Any cigar/wine/port pairing recommendations?