I used to work at a headshop we sold cigars.
I like "Acid" brand cigars... they are the smaller ones (forget the fancy name for the cigar size) but they have a silhouette of a guy leaning on a bike with dreadlocks as their "emblem" or w/e. best flavor was vanilla bourbon.
They were lightly flavored and I liked them the best. they were 4.99 or 5.99 per cigar.
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loginStay away from anything lower than 4 dollars per cigar, in my experience they are never good. Find somewhere that stores their cigars in a humidor or environmentally controlled. If they are just sitting in a box out in the open they are probably really cheap or ruined and/or too dry.
Also most of the ones you will find in a glass tube w/ a cork top are fairly high quality. Most of them.
You can always ask the person behind the counter too, if it's a smokeshop they should be semi knowledgeable... If they are like me they spent a lot of time reading the free cigar magazines vendors give to the headshops.

If that fails just buy the more expensive ones, you can always taste the difference between a cheap 2-3$ dollar cigar or a 10$ cigar. Unless you've never smoked a cigar before.
Sadly I don't know anything about chew... never tried the stuff.