Wish You Were Here (1990)

There are 6 episodes, and since I don't believe they actually have titles, I'm going to title them here after whichever city Donny visits in that episode. The show is about Donny Cogswell, who quits his job after buying a video camera. After some other things go wrong in his life, he decides to get away, do some travelling. In each episode, he sends a video tape of his travels to people he knows.