First start with a cob pipe, preferrably a Missourie Meerschaum. Cheap and you can probably find it at Walgreens.
On tobacco, don't jump to aro's, flavored goopers. You'll want something kind of dry. While they may be
listed as aro's Carter Hall and Prince Albert are great starters and also at Walgreens. If you like those and
want to continue then sign up for the newby trade and look into some english and va.per blends.