I smoke a pipe when I go camping, sit in a hot springs, when hanging out with college buddies, etc. Probably 2-3 times per year at this point if even that, but I do enjoy it when it happens. My wife likes the smell of pipe smoke so it doesn't bother her. I used to work at the county court house, one of the old guys who would come in every morning wore a velvet suit jacket and always smoked a pipe in the morning before he came in, made me instantly want to go home and smoke mine.
A quality pipe is important. There are $15-25 pipes all over the place, but they are garbage and will ruin the experience for you. They are hard to keep lit, they burn too hot, you constantly have to mess with the stack, etc. I got fed up with the POS I had and went to the local smoke shop, the owner gave me the low down on how cheap pipes are useless. I bought a $50 (on sale, usually $80-100) churchwarden style pipe from him and very much enjoy smoking that pipe. It is still not a "high end" pipe, but it is much better and the smoke is much better. Similar results could be obtained with a more traditional style pipe I am sure, but I liked the look of the one I bought and it works great so I am happy with the churchwarden style.
For tobacco, I usually go with a bag of whatever is mixed by the owner of the smoke shop. He has various flavors in his own packaging and they are usually pretty good. I like the darker stuff personally, some like the lighter stuff. The advantage to going to a real smoke shop is you can smell everything and see what appeals to you. Also you can buy small bags of different tobaccos so you aren't wasting a bunch if you don't like a particular flavor. Any mass produced tobacco I have ever found I am not a big fan off. Much prefer small bags from local shops. The other reason to buy a small bag is the tobacco will dry out which ruins the smoke. As I don't smoke very often, I waste a lot of tobacco even when I buy the small bags.