Hey Mike, I've been smoking cigars (in any kind of serious way) for about 10 years now. I also used to work nights and weekends in a nice tobacco shop in the KofP mall.
There are a lot of great cigars out there and there are a lot of crap. One thing to keep in mind is that a different brand name may not mean that much of a different cigar. Many brands are produced by the same parent company and rolled in the same factory by the same rollers. Major manufacturers include
Altadis,
General Cigar,
Fuente/Newman,
Davidoff,
Padron,
La Flor Dominicana, et.al. These manufacturers (Cuba aside) probably make up at least 80% of the handmade cigars readily available to Americans out there.
Cigar construction is divided up into 3 parts: filler, binder, and wrapper (plus a "cap", but that's made with the same leaf as the wrapper). It can take 20 years to become a "Master Roller". A would-have-been great cigar can be a bad experience if it's poorly rolled (too tight). The filler is a blend of various tobaccos to give the cigar it's core flavor character and nicotine presence. The binder is of similar leaf to the filler and it's purpose is to hold everything together. The wrapper is the most delicate leaf and lots of care is put into producing this leaf.
First you have to decide whether you like stronger cigars or mild cigars... or want to start mild, then move into stronger cigars. Here is a
very generalized description of cigars according to strength:
Strong: medium colored (wrapper), may have an amount of dark tobacco in the filler (look in the "foot)... this may be strong ligero tobacco, often not very long (this is because ligero tobacco (strong) is a short leaf and they can fit more whole ligero leaves proportionally in a shorter cigar than they can in a longer cigar). A good example is Fuente's Chateau Sun Grown or a Joya de Nicaragua Machito.
Medium: medium to dark colored. Maduros are typically medium-bodied. Length is variable. Flavor varies from bland to chocolatey (maduros). A good example are most Punch or any of the standard line Padrons.
Mild: Usually light colored due to the connecticut shade wrapper. Flavors are smooth, creamy. Some smoke like air (Macanudo!). A good example is any Ashton (made by Fuente).
I love pretty much anything by Fuente. Start with them and you can't go wrong. They have many different brands and a whole range of mild to strong cigars. Try an 8-5-8 Natural... it's their flagship smoke, medium bodied, nice flavor. No one ever accused them of making a bad cigar (that I've ever heard). Plus I've met Carlito Fuente and he's a great guy with a deep passion about cigars... plus he gave me an unreleased Opus xXx Maduro out of his pocket.
Sorry for the long post... you've got lots of great info on here already (except for the Baccarat comment
). Cigars are a passion of mine so I love talking about them... kind of like brewing.