The best I could do...Vermont is not for pipe smokers

it keeps getting better and better.

I smoked cigars occasionally before I started smoking a pipe.  You may already know all of this, so forgive me for boring you if that's the case, but there are several errors that can be made when switching from cigars to a pipe.

Firstly, I recommend that you start with a full flavored tobacco.  If you choose a mild flavored tobacco, you will likely pull too hard and/or too fast to get more flavor and will burn your tongue.  I think English blends, i.e., ones with Latakia, are the best ones to begin with if you are coming over from cigars.

One thing I initially did wrong, was to try to get voluminous clouds of smoke similar to what a cigar produces.  That's generally wrong for a pipe. If you pull too hard and/or too fast, your pipe will get hot, you will scorch tongue, and you won't be able to taste the tobacco as well or perhaps at all.

Another thing I did wrong was to try too keep the pipe going on the first light.  When lighting a pipe, there is a first false light, before a second in which you actually light your pipe and keep it going.  The proper way to prepare, fill, light, and smoke your pipe is to:

1. Dry your tobacco a bit before you load it in your pipe.  Some tobaccos are dry enough right out of the tin/pouch/jar, but many, if not most, need a little drying time.  I live in a dry climate, so 15 minutes usually works for me.  If you are somewhere with high humidity, you'll probably need to dry it longer.  You don't want it crispy, just not damp.

2. Load your pipe.  I simply gravity load it, but other methods work well too or perhaps even better.  Don't pack it too tightly.

3. Gently light the surface tobacco and then let it go out. This is the false light.

4. Gently light it a second time and then continue to puff slowly and gently.  You'll get a nice cloud of smoke initially, but afterward you actually just want to produce a small amount of smoke.  The tobacco will taste better if you continue to puff gently, and slowly.

5. If it goes out, gently tamp, relight, and repeat as in 4. above.

6. If the ash starts to smother the tobacco, gently dump the ash, tamp, and relight.  Don't ever stir the tobacco, as that will mix ash through the unburned tobacco and send it up into your mouth, as you experienced.

7. Repeat 5. and 6. as necessary until your tobacco is consumed, or until it no longer tastes good and/or burns well.  Don't worry if you stop when there is still some tobacco in the bowl. Some blends burn wet, and the bottom portion will be too wet to burn and/or can taste foul.  That's dottle, and should just be dumped.

I hope that helps. Happy smoking.  

One bit of unsolicited advice I would give - go easy on the temptation of PAD. (Which is Pipe Acquisition Disorder (or ‘Disease’). Many of us go kinda nuts when first starting out. It’s pretty easy to end up with a ton of ‘cheap’ production pipes. Most of mine ended up in a box somewhere and get little smoke time. I have far too many ! I could have bought several custom pipes from artisan makers for what I spent on lower end production pipes. ‘Cheap’ pipes can end up costing a guy a lot of money !