Pipe smoking is what separates man from the animals.
Starter pack:
Missouri Meerschaum corncob pipe
These go for some $10-20 and last for decades. They're easier to use -- and often smoke better -- than many briar pipes, and are much cheaper than (decent) briars and meerschaum. Make sure to buy name brand, the Chinese knockoffs break easy. Again: name brand lasts for decades.
Pipe tool
These are cheap and come in many forms. The best ones are those cheap little metal ones that go on your keychain. I like these because it helps me to never lose my keys. If you're cheap, you can get away with a nail or a stick. The most important part is the tamper; as you smoke through a bowl of tobacco, you will occasionally need to tamp down the burnt tobacco to insulate the flame and keep things burning at a nice temperature. The poker can also be useful for loosening up a bowl that's been packed too tight, cleaning a pipe, and anywhere else you need a poker in daily life.
Pipe cleaners
Every time or so after you smoke, you'll need to use a pipe cleaner on your pipe. Use your pipe tool to get larger bits of tobacco out of your pipe's bowl. If you need to disassemble your pipe in order to clean it, wait until your pipe cools completely (at least an hour or so after a smoke) before disassembling. Run cleaners through the stem until clean, then fold the cleaner in half and scrub inside the bowl until clean.
If your pipe starts to keep a funk smell or funk taste, soak the ends of your pipe cleaner in strong and tasty drinking liquor, then clean pipe as normal. Let air dry.
Pipe tobacco
No, not roll your own tobacco. If possible, you'll want to buy tobacco online; if you have a proper tobacco store in your city, you can try going there, too. Try buying a few sample-sizes of pipe tobacco: especially burley, virginia, and English blends.
- Burleys taste a bit nutty and chocolatey, are the easiest to smoke, and most resemble cigarette tobacco
- Virginia tends to be more grassy and sweet, but also burn hotter. They take patience to smoke, and smoke better dry.
- English are more complex, rich, spicy, and can be reminiscent of a cigar. This is partially due to a leaf called Latakia being present. The flavor can be a bit polarizing -- if an English blend is too strong, mix with some burley or virginia leaf to balance it out.
- Aromatic tobaccos are NOT RECOMMENDED. They can have a wife-pleasing aroma (relative to other kinds of tobacco) but have little-to-no flavor. Cherry, vanilla, whatever -- they smoke very hot, taste like steam, and gunk up pipes. This is not to say that they are all dogshit, but many are; the best use is to mix them in small quantities with stronger tobaccos to tone down the flavor and temper their smells.
Unlike cigarette smoking, the focus of pipe smoking is entirely on the flavor. Regardless of what blends you decide to go for initially, this is where a lot of the fun of the hobby is: looking for tobaccos, reading reviews, trading with friends, blending your own mixes, aging tobacco. As best you can, store tobaccos in glass sealed jars away from light in mild temperatures.
Buy more tobacco than you need! Aging tobacco improves flavor.
Your tobacco may be too wet, straight out of the jar (practice will inform you on this) -- some tobaccos do better if left out for a bit before smoking, and some people even microwave tobacco for 3-5 seconds.
There are 10,000,000 guides on how to smoke a pipe online. Even if there weren't, it's not rocket science. I'll just give share primer here:
First, do not inhale your pipe. Second, don't pack your pipe too tight; it should be a bit springy and it should be easy to draw air through the stem without too much effort. If your pipe is packed too tight, use the poker on your pipe tool to loosen it up a bit. Third, smoke slow and smoke cool: a pipe should last you around an hour, if not more. Smoking fast&hot ruins the flavor, can damage the pipe, makes the tobacco produce a lot of moisture that can make the smoke unpleasant.
The main focuses of pipe smoking are relaxation and flavor. Be patient. Take your time packing, take your time lighting, take your time puffing. An easy technique for beginning pipe smokers: while keeping the pipe in your mouth, breathe in and out through your nose as usual, forgetting about your pipe. Your mouth will slowly fill with cool, rich smoke; remove pipe from mouth, savor the flavor, and slowly breathe it back out through your mouth. Blowing a bit of pipe smoke through your nose from your mouth from time to time (called snorking) can really help bring out flavors as well.
With great technique, you'll pack your pipe, light it, and smoke it clean to the bottom. In practice, especially if you're beginning, you may have to relight your pipe several times. This is largely due to keeping a bad smoking tempo or smoking tobacco that's too wet. Relighting shouldn't have much impact on flavor. As you get deeper into a pipe, removing some of the ash on the top can also help the cherry keep itself as it should be.
Pipe smoking wet? You probably need to let your tobacco dry more, or improve your smoking tempo, but here are some more tips. If it's a filter pipe, smoke with filters; if it's a straight pipe, run a cleaner through; if it's a bent pipe, well, unless it's an "army mount" pipe, you can't disassemble it while hot in order to clean it, or else the pipe won't want to fit back together again, so that sucks. I have found that cheap pipes that consistently smoke wet can be partially improved by sprinkling uncooked rice in the bottom of the pipe before a smoke, at least to cover up the draw-hole a bit. It'll help absorb the moisture -- but not solve the problem absolutely
Don't feel like smoking your pipe all the way down? That's totally fine! Let your pipe naturally go out on its own and scoop out any of the ash. When you come back to it, you may find your pipe tastes better and is easier to smoke than before.