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.
"If you look for truth, you may find comfort in the end; if you look for comfort you will not get either comfort or truth only soft soap and wishful thinking to begin, and in the end, despair." -C.S. Lewis, Mere Christianity
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