While it wasn't the single best smoke I've had (in my entire month of pipe smoking tenure), I think it has to be the huge bowl of Samuel Gawith's Full Virginia Flake mixed with Gawith & Hogarth's Skiff Mixture.
I bought and mixed those two upon reading a reviewer noting how this was what he'd settled upon as his closest replacement for that Dunhill Nightcap I've read about it legend and lore. I immediately loved the scent of the Skiff, which is far nicer than it's name suggested to me, and of course the Virginia Flake is pure and delectable.
It was smoked in the second pipe I purchased, a Missouri Meerschaum Corn Cob Cobbit Wizard Churchwarden—a lengthy name for a lengthy pipe as seen here (
https://www.mysmokingshop.co.uk/newShop/images/products/17591__big.jpg) and the reason it's solidified as the game changer is twofold:
I managed to actually taste the tobacco for the first time, previously having been disheartened by some wonderful whiskey scented aromatics bought in a pipe shop after smelling them and thinking I was going to taste that rich sweet aroma, so actually getting even a small fraction of the peppery English scent when smoking was a huge achievement as I was going to write the whole thing off if it all just tasted of airy smoke.
Secondly, it lasted a long time, maybe 45 minutes, which actually isn't very long at all considering how absurdly deep the bowl is. Before I could keep a pipe lit for more than a handful of draws, I'd burn through the tobacco through a combination of frequent lighting and rapid puffing to keep it going, and so the whole thing was over in about 15 minutes. I now find that even an average sized bowl lasts about 45 minutes, which is fantastic and another thing I'd wanted from my new indulgence.
All in all, it's more akin to managing to ride a bike without stabilisers and go in an almost straight line without falling off - I've had more amazing bike rides since then but the thrill of 'doing it right' and the successful feeling of knowing you hadn't spend that money on a failed venture made it the most memorable.