Education, experience, environment, equipment. That's all it takes to get the most flavor out of your pipe. Simple, right?
Consider that you might be tasting all there is in your smoke, but you simply lack the flavor-vocabulary to describe it. Try reading this while smoking your next pipeful to see if it helps to isolate flavors. Start with broad themes and filter down.
http://pipesmagazine.com/schmitzbitz/pipe-smoking/tobacco-flavours-and-nuances/
this next is cigar specific but more orderly
http://tobacconistuniversity.org/pdf/flavorchart.pdf
Experience and technique also play a part. You can puff away absently on codger blends and some englishes and have a nice smoke, but doing so with a VA flake will get you nothing more than hot air and a scorched toque. Is your technique good enough to get the most from your tobacco? For most new folks the answer is a resolute No.
The best technique won't help all that much if you're smoking outside on a windy or wet day. Smoking indoors is a windless room will always allow for easier tasting.
Lastly, tobacco prep and the overall state of your pipe play a large role in what you taste. Dirty, gunk laden pipe, or a clean, but mildly ghosted pipe..over wet or over dry tobacco...it all can contribute to degrading what you'll be able to taste.