OK, back from pizza (and Pinot Noir-- but I'll try to stay coherent). Alcuin has already mentioned some things I was going to add. You might consider getting a corn cob pipe or two; they're cheap, you don't have to break them in, and, though they eventually burn out, you can just toss them when that happens, or when they get fouled with goo. Which is probably going to happen. Alcuin talked about tobacco, which I was going to bring up. You mention a vanilla-flavored blend; would I be right in guessing it's black, or mostly so? It's called a Toasted Cavendish -- Captain Black is probably the most popular commercial brand. I don't much care for it myself, partly because it uses cheap burley tobacco which can absorb huge amounts of flavoring syrup, but mostly because I don't really like flavored tobacco, called "aromatics". But I have to admit I started off with them, at age 17. In fact, almost everyone I knew back then who smoked a pipe seemed, like me, to have started with a Dr. Grabow pipe and Cherry Blend tobacco. I eventually switched to a plain Cavendish, particularly a Dutch blend called Troost (wonder if I still have those coupons? ). They quit some years ago, though I believe an American company now has the rights. Sail Natural is a similarly light, smooth blend. Anyway, when you get tired of digging soggy tar out of the bottom of the bowl, you might try one of those. For the past couple of decades, I've smoked an English blend, something you may not want to try for a while -- it's not for the faint-hearted! It usually contains a mixture of matured Virginias, Latakia, and maybe some Perrique; some heavy duty stuff, as Alcuin says. This, BTW, is probably what Tolkien smoked, in one blend or another. UK regulations limit (or used to) non-tobacco ingredients in a domestically produced blend to a minimum: no more than 3%. By contrast, some blends are as high as 30% flavorings. I'd rather taste the tobacco than chocolate or whiskey. I buy Rattray's Black Mallory, when I can afford it, a heavy Scottish blend, though now made in Germany. My all-time favorite was the original Bengal Slices, no longer made, sadly, at least in the original blend. Enough nostalgia. Yes, you definitely need a pipe tool-- many people give up because they "couldn't keep it lit". As the tobacco burns down, it needs to be tamped -- gently -- but this comes with practice. I'd suggest starting with a cheap 3-way tool from the pipe shop--under a dollar, and has what you need to begin with: tamper, pick, and spoon. Oddly, I've never had a big problem with excessive caking -- maybe because the mixture I use is fairly dry, due to the lack of flavorings, or maybe I just don't smoke any one pipe often enough. Which brings me to the admission that I haven't bought a pipe at retail in years; the last twenty or so have been picked up at junk stores, yard sales, and flea markets. Do not laugh! I believe the last pipe I bought was a King Size Italian Caminetto, for five bucks. So there. Or something.