I'd welcome sticks way more than a snip or other paraphernalia. Anyone who smokes cigars already has the accoutrements.
I haven't partaken for a few years but Ramon Alones was a good Cuban. Monte #2 is the world's #1 premium cigar, I think, but that means it's a plain vanilla choice for a regular smoker.
If the dude is Cuban, I'd be tempted to buy from elsewhere, since it's unlikely you'll hit on something from his country that he doesn't know about. And, don't repeat this to him, but I had a rotten run of Cubans that were rolled way too tight. Montecristo and Romeo were the prime suspects, as I recall.
I can't remember a particular brand, it's been so long, but Hondurans and Nicaraguans (edit: + Dominicans) are generally well regarded. On the other hand, I suspect all the latinos kinda all hate each other, like asians do, so you don't want to piss the guy off, lol.
I'd go for a domestic. American cigars aren't nearly as earthy and heavy as a Cuban, but that can be a good thing, even for a daily smoker. I was often in the mood for a lighter smoke on summer nights after lighter fare. Again, I couldn't recommend any particular brands but I suspect Connecticut Shade wrappers are generally a sign of premium quality. I've never tried a "dutch" filler but I've heard good things, and it might even be something he hasn't experienced. I think it's uniquely American, despite the name. It was actually Deutsche, grown by German immigrants, but the dumbass Americans thought they said Dutch and the name stuck.
Sorry I can't be more helpful but the taxes here are beyond obscene so, much as I like 'em, I'm out of the loop. A true cigar specialist store, particularly in NY, will steer you right, I'm sure.
Idk if this will be relevant but my understanding is that demand has been outpacing well matured production for awhile, so "go to" brands have been rushing things to market a bit and not cellaring the way they used to. If the sommelier (is he a fumarier?) is on top of things maybe he can point you to a Goldilocks maker, big enough to be serious with a solid flagship smoke, but not so discovered as to get bought out.
I'd play it safe with a down the middle style. There's a hundred names for shapes and sizes but go mid length and mid to mid large girth unless you know different. Nothing skinny since they can't contain enough leaf mix to give it depth and development. Basic brown wrapper (of excellent quality tho). Oscuros and candelas and other exotics are best avoided unless, again, you know he digs 'em. Definitely avoid, imo, "nifty" rolls, like entwined serpents and such, unless the dude is an incorrigible attention whore or something. Rock solid basic > than cool looking shit.
I don't believe in "bloom." Maybe I'm wrong but I say it's fucking mold. Idk if I'd buy anything with bloom on it.
Just be sure to ask them to wrap them up well, and let them know you're not on the way home to a humidor. You don't want them to dry out between purchase and presentation.
