I won't be able to hang out this weekend, but send Cgardan a pm. There's the velvet lounge in the east village near Criff Dogs (awesome hot dog place). Merchants is a more upscale place at 61st and 1st or 2nd ave, can't remember. Also, enjoy a walk in central park while smoking a stogey, or walk the brooklyn bridge at sunset doing the same thing.

As far as stores, there's JR Cigars on 5th, Nat Sherman also on 5th (both within a couple of blocks), and many other local places. With NYC tax though, better to bring your own.

Hope this helps.