Hi Eric, I should answer you because I am a cigar smoker, but I am not pros for wines. For me, I used to pair with red wine for cigar, since cigar will give you a little bit bitter and spicy taste, so me and my friends will choose some fruity red wines, Port wines, dessert wines (for rich taste cigars ie Cohiba). But if just limited white one, I will suggest Champagne or sparkling wine.

If your friends want high alcoholic one, I will suggest a bottle of Whisky, since both aromas from wines and cigars is a very good pairing.

Eric, I've had considerable experience with wine and cigars over the years, and have a few friends like yours who are fiends for cigars first, and wine second, even though they claim to be serious about good wines. I tend to be the reverse, though I do enjoy good Cubans from time to time, maybe once or twice a week at most (for reference purposes, I have never smoked cigarettes or pipes, and an occasional cigar is the only tobacco I smoke). These fiends are into even better Cubans to the tune of three a day, in some cases.

I thus have had to cope with the same problem you're facing. Distilled liquor is an easy call, and good brandies and whiskies and rums always work. Fun to dip the smoking (not burning ;-) ) ends of the cigars in the liquor before taking a puff. But I don't think you're asking about that. The short answer I have vis a vis wine, is Port. Second choice some Madeiras and sweet Sherries and the like.

I am very sensitive to the olfactory and taste sensations of wine, and don't like cigarette smoke in the air, much less cigar smoke, when I'm tasting, whether with food or without. I've had to put up with both on occasion, but they are interference just in the air, much less if they get in my mouth and throat while drinking wine. The range of sensations I'm able to experience and enjoy of the wine when smoking is cut down to less than half. So I always try to avoid having good table wines with smoke in the environment.

I don't mind as much with ports and madeiras and olorosos and even marsalas, though. Perhaps also a Vin Santo. Since I also prefer smoking cigars after a meal, rather than on their own, this is an even easier call.

The ports seem to stand up to the cigars better, and I can still enjoy them even with the smoke. The sweetness and alcohol of the fortified wines counterbalance the nicotine, etc. I haven't had as much success with Sauternes or late-harvest German wines. Perhaps it's a varietal (as well as a color or alcoholic percentage) thing...

Sounds like vintage Port may be the way to go. Maybe I'll bring a pre-game bottle of something from my cellar but then go for the Port when the time comes to light up the cigars.

Any suggestions of something that wont be too hard to find. I'm a bit ignorant when it comes to Port.

Sorry, somehow Warre's slipped from the list of houses producing ports that I've had a lot of. They would fit in the middle of my rankings by the no. of bottles I've consumed from them.

I prefer Italian Reciotos and in particular, late harvest zins to port for pairing with cigars.
The slightly lower alcohol is less of an overall assault on my senses.

The spicy fruit of the late harvest zins stands up perfectly to a nice cigar for me. Heck some of the "regular" high end zins have enough sugar ad sweet fruit to stand up to a cigar.

Dashe and Ridge make my two favorite Late Harvest Zins.