While I do not live in San Antonio (I used to), I can recommends some great places to try to 1) buy cigars and 2) herf.
Cigar Club at 1604 and Stone Oak. Great atmosphere. Overstuffed leather chairs, live jazz in the evenings, good selection of cigars, full bar. Great place to smoke. My old haunt in SA.
Club Humidor in the Quarry Market. Much better selection of cigars and better prices. Leather couch and free coffee. Very helpful staff. The owner is a friend of mine. Definitely give it a try.
Club Cohiba is a cigar lounge in Hotel Havana in downtown San Antonio. It is on a little used part of the riverwalk. Nice, but very dark. Quiet last time I was there. Full bar.
Swigs is a martini bar on the riverwalk that is also cigar friendly.
If you are at the Cigar Club or Club Humidor, ask if Larry Carrera is around. He is one of my best friends in the world and a fellow cigar lover.
You guys have a blast. Wish I could be there.