Things you'll need
1. Pack your pipe to about 75% full, to allow space at the top for the lit tobacco to "bloom." Most people recommend a 3-Step packing method, but sometimes I only need to do this twice. Here are some guidelines:
2. Don't pack so tightly that a test puff feels like a milkshake, or so loosely that it feels like no resistance at all. You want it to feel like sipping water or soda through a straw.
3. For the First light, take sips (not gulps) and move the flame around until the top of the tobacco is evenly lit. It will most likely bloom up and go out quickly. This is known as the "false light."
4. Once out, tamp the tobacco gently and uniformly. This is the “cake” or burning surface that you'll use to get your true light.
5. Light a second time the same way as the first. You should be on your way, but it sometimes takes a third light to really get going.
6. Tamp gently along the way whenever the top gets looser. Once you've smoked for a while, the top will get moderately "fluffy" with ash; gently upturn your bowl and tap the loose ash in an ashtray. A coffee tin or any similar metal or wooden container will work.
7. Take gentle sips and enjoy the taste of the tobacco. Congratulations, you're smoking a pipe!
If your tobacco is moist, leave it out to let it dry a bit. Moist tobacco causes too much hot vapor in the smoke, a large contributor to what is known as "tongue bite."
Don't fight to keep it lit! You'll only frustrate yourself and burn your tongue. If the smoke tastes too hot, let the pipe cool down for a bit. If it goes out, just tamp and relight. Take your time, be patient. Pipe smoking is about relieving stress and enjoying the moment.
Don't inhale! It's not a cigarette, and shouldn't be treated as though the point were to get a fix.
Learning a cadence that keeps the pipe lit better for you, yet doesn't make the smoke too hot to enjoy, is a knack only learned with time and experience. Your cadence won't be what another pipe smoker's cadence is, so don't compare. Just learn what works best for you!
If you don't like the first tobacco you've tried, don't give up: There are literally HUNDREDS of blends to choose from. I always recommend trying at least one of the following 5 blends before throwing in the towel: An Aromatic, a natural Virginia, a natural Burley, a Latakia Blend, and a Perique Blend.
That's it! Of course, pipe smoking is a nuanced and highly personal activity that you will get better at over time. But these general tips are all you need to get you on your way!