This is a great thread. I'd love to get into cigar smoking some time. Totally different than smoking cigarettes - which I don't.
Cigars are great, very manly enjoyment. If you have any smoke shops around, check one out and see if they have an enclosed cigar room. Keep in mind though that there is a lot of "professional" advice in the cigar aficionado. In this case, don't be afraid to buy some cheap factory cigar for "practice."
Anyways, here are some things you'll want to know in terms of how to buy and smoke a cigar:
A good premium cigar will cost around $5 at least (for a single one). There are a ton of different kind of cigars, so take a look around at all the boxes with pretty Hispanic artwork and find one that looks appealing to you for a starter. Remember that cigars will take a long time to smoke, so if you don't plan on spending an hour or more smoking one, then try to find a smaller size. I don't think there is a whole lot you can do to pre-determine if a cigar will be good, but obviously if it's hard and dry, it's not going to be good. You might also want to stick with mild cigars at first, which usually have a lighter wrapper, and then later try darker, bolder ones.
A cigar cutter is practically a must. Sure you might be able to get away with a sharp knife, or your teeth if you absolutely must, but buying just a typical cigar cutter will give you much better quality and convience. I just bought a cheap one at the tobacco shop I usually go to and I think it was maybe $2-3.
Not only is a cutter important, but so is a lighter. Aficionados will shun the idea of using a standard gas station Bic lighter, and while I don't think those are totally bad thing to use, it's best to use other methods. The typical cheap Bic lighter gives off a fume when struck, which can effect the taste of your cigar, so you're going to want a lighter that gives off as least scent as possible and preferably burns hotter. Those super hot "jet" lighters are great if you can find them, but if you can't, look for a quality butane lighter that doesn't give off any smoke when lighting. Some cigar smokers are not keen on the idea of using Zippo lighters either as the wicks in them can also give off some foul scents, but I've never tried it myself. As far as matches are concerned, use wood matches, because like unproper lighters, paper matches also give off bad scents.
When cutting the cigar end (the rounded part that you'll be placing on your lips), you'll only want to cut a little off. It's kind of hard to explain in text, but you'll want to cut so a little bit of the roundness is present so that it leaves a tight end to smoke out of, but you don't want to cut it too short or else it will be too tight and you would get as much smoke and flavor. You also don't want to cut too far ahead or else it can unravel the wrapping a bit and it can get bits of tobacco in your mouth. Just carefully align it and give it a smooth clip. A lot of cigar smokers, myself especially, prefer to "wet" the end before clipping by rotating the cigar in your mouth. Not necessary, but it's fun
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The lighting process is definitely the biggest learning curve. You should be able to find a bunch of links on Google explaining how and I'll post some good YouTube links below. Some things to keep in mind are to never let the flame actually touch the cigar when lighting (don't worry if you accidently do), "toast" the foot before the actual puff and light process, rotate the cigar and flame to make sure the cigar is evenly lit (this is the hardest part because it's easy to unevenly light one and you'll regret it), and most importantly, to take your time.
And my last advice is to do what you feel comfortable with. There are many different aspects on choosing, lighting, and smoking cigars, so do what you like best because it's about you enjoying the cigar.
Here is my favorite cigar lighting tutorial on YouTube that I watched many times for practice -
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Here is another great video that's a clip from a great cigar documentary on YouTube -
And here are the links to the mentioned short documentary -
And here's a super relaxing video of an awesome old dude smoking and talking about cigars and pipes -
I like to take the tobacco out and roll them myself
Do you buy the Phillies Blunts?