Club Mac is nice, a bit stuffy for my liking, but that's me. I haven't been to Merchants. Another place you might consider is actually a restaurant in Little Italy (what's left of it at least) called Florios. It's a good Italian restaurant that is extremely smoker friendly. In fact, you have to go through the smoking section to get to the non smoking section. It's on Grand or Mulberry, can't remember which. There is also Hudson Bar and Books. It's a bit small but very nice. Of course there is the Davidoff store in Columbus circle, very chic.
