I know that this goes beyond simple "stressing out" over a trip for you, but something that helps me deal with trip stress is to make lists of everything I can possibly think of that needs to be done or needs to be taken, and I do this starting about a month before the trip. Gives me something to review when I start worrying that I'm forgetting something before I leave.

I'm not afraid of flying; but I hate how much of a hassle travel by plane has become in the USA. I don't plan on flying again unless it's completely unavoidable. My next trip across country I'm traveling by train, in a sleeper room.

And I'm going to wear a cream-colored crushed velvet suit, sit on the observation deck, and watch the country go by.