Well, I had my VSG last weekend. I got a bottle of Dalwhinnie 15 for my birthday and grabbed a bottle of Stone Points Unknown IPA (DIPA mixed with Belgian tripple). Both paired wonderfully! I was skeptical about the IPA because of the strong finish they have but it didn't interfere with the cigar at all (or vice versa). They worked together really well.
The Dalwhinnie was great with it, too. As
@
gunnermcgee
pointed out, the vanilla/sweetness of the Highland scotch worked super well with the pepper and nuttyness of the cigar. Thanks for the great recommendations!