Tobacco Bar LTD
6613 Seybold Rd (west side of Madison)
608-276-7668
Kind of off the beaten path but good selection of cigars. Not a bar that serves drinks, only cigars and pipe tobacco. Nice lady who leaves you alone while you're in the walk-in but will answer questions if you have any.
Madison Wine and Cigar Room
7003 Watts Rd
608-276-8676
Only a few blocks from Tobacco Bar and easier to find. It's at the corner of Gammon and Watts, close to the Sam's club. Friendly guy who owns it and he has a small bar, I mean very small, where you can drink a glass of wine and smoke a cigar. Good selection in his walk in most of the time and is very knowledgeable.
If you're downtown or on the south side and like beer, try The Great Dane. Here's their web site:
http://www.greatdanepub.com/There are three Tobacco Outlet Plus stores
2401 Broadway (close to Monona, a suburb south of the airport)
3868 E Washington (close to the airport)
6621 University Ave (west side almost to Middleton)
These places don't have the greatest selections but are less expensive)
There are a few other places but I haven't been to them so I don't what they are like.
Have fun in Madison this year because next year Madison will become smoke-free even in bars. Just curious, what kind of biz are you in?