85% of my smokes are with wine. Not an expert, but trying to get there (took a few courses at the New England School of Wine to learn some of the basics)....
I pair my cigars like fighters, heavy weights with heavy weights, light weights with light weights. I Pinot Noir with a natural leaf, a maduro or strong CC with a Chianti or a bold Zin. I wish I had a more educational answer, but as thats what has worked for me in the past.....
My goal is to learn as much as I can about wine and cigars. This place has been my one stop shopping for an education on cigars.....
Good luck bud and please let us know what you discovered after your pairing.....