Thanks for the comments guys, I will take a look into that book. I wish I could afford to do it in a Stearman!
I think it will not only improve skills but my confidence to. Long distance flights through all sorts of different weather and terrain. That and yes, it will be great fun! May have a friend or two come long (depends on where I want to fly and what A/C etc) to keep me company.
I did read a few months back about some guys who did a similar thing and booked a slot to land their 172's into JFK! Might steal that idea!