For my son's first Christmas, I plan on starting a tradition of buying a fine bottle of wine each year, in order to present him with a nice wine collection on his 21st birthday (maybe 25th--if someone had given me booze on my 21st, it wouldn't have lasted too long.)
I'm seeking recommendations, therefore, on a wine or port that will cellar well for at least 20 years. Price range is between $40 and $75. (I'll probably also buy a bottle of the same for myself, so cheaper is better.) I live in Chicago, so availability should not be a problem.