I would most certainly choose to fly commercially to the west coast and rent from there. The scenery is absolutely fantastic. Just picture the snow on the top of the peaks of 12,000' with you flying at 10,500' between the pass... flying over deserts, plains, forests, mountains. The many varied scenery flying opportunities in the western states are plenty.
Like Keef the most I could personally handle in one leg is L.A. to Grand Canyon in an Arrow III but that was with another pilot and his wife (ensuring us two up front stayed awake). In the same day we went to Sedona and then a near three hour night flight back to L.A. Seven hours in one day, that was really hard going, I just flaked out after writing up my logbook. I certainly wouldn't have done 7 hours on my own, would be too much imho.
My next flying holiday will be Florida to New York, across to Chicago and then back to Florida via New Orleans. This will be something I've not done before but is planned with another pilot with me (we'll be sharing the flying). We're planning on going the end of next September. Oh before then is my CPL/IR course in Florida next April but that will not be a holiday! ;-))) Now all I have to do is speak nicely to my manager at work to allow me to have another two - three weeks off... otherwise it'll be summer 2004 that I'll be doing the New York trip. :-(((
Best wishes,
Charlie Zulu