I've been messing around with wine pairings, and have found...
Napa Valley Cabs tend to pair great with fuller bodied maduros like the RoMa Craft Cromagnon.
Chianti tends to work well with cigars like the LFD Double Ligero.
A nice oakey Chardonnay works well with cigars like the Caldwell Eastern Standard.
wine is pretty new to me so it's been fun exploring some wine and cigar pairings. Just be warned that some of my pairing experiments with wine have proven to be terrible