As I said in the OP, I don’t know enough about the topic to know what my interests are.
If someone approached me and said they’d never drunk wine before, but wanted to try it, then I’d recommend something a novice would enjoy, but still was still representative of the medium. Maybe a pinot noir: it’s light and sweet enough that it won’t be overwhelming for the new wine drinker, but it’s still dark enough to embody that certain wine-ness that one gets from most vintages. And simple enough that no experience is needed to appreciate it. That’s the sort of thing I’m looking for in a cigar recommendation.
All that said, however, I am immensely enjoying the responses so far. Someday, when I have both the means and the ability to appreciate a complex cigar, I’ll come back and check out all the recommendations here. In the mean time, there are definitely a few tips here that sound perfect for the cigar newb.
I am not a huge cigar smoker, but I have a few now and then. Like a couple of other (surprisingly) I am more of a pipe tobacco guy (did that thread ever start?).
But, my favorite, hands down, is the stuff made by La Gloria Cubana. I like Dominican Cigars a lot, followed by Nicaraguan, and in fact, that is what I would go by first when picking out cigars. Start by trying stuff from a similar country of origin. If what you normally smoke is from Nicaragua, look for other Nicaraguan Cigars, if it’s from Cuba, look for that (if legal). Cigars are a lot like coffee that way. Where they are grown has a huge effect on flavor.
All that said, Sancho Panza makes a great inexpensive cigar as does Nat Sherman.
I have a link at work to a really good cigar specific discussion forum too. Oh, and have you given any thought to smoking a pipe? I could help you get set up with some quality stuff for about half the price of a box of cigars…just sayin’.
OP, based on other discussions I’ve had with NAF1138, he could certainly help you with a pipe. I’d offer my advice also, for what it’s worth. I think we really need a pipe and pipe tobacco thread!
Aside to NAF1138, re a question he once had about one of my pipes: My pipe was much like the one in the photo I linked to, except I think it has a nicer grain pattern.