I've done a lot of different Amtrak trips over the years (in every part of the country, actually), but the most elaborate one had this itinerary:
- Madison
- Milwaukee
- Seattle (42 hour trip on Amtrak "Empire Builder"; two days in Seattle)
- San Francisco (23 hour trip on Amtrak "Coast Starlight"; one day in San Francisco)
- Santa Barbara (nine hour trip on Amtrak "Coast Starlight"; three days in Santa Barbara)
- Los Angeles (three hour trip on "Coast Starlight"; transfer in Los Angeles)
- Austin (35 hour trip on Amtrak "Texas Eagle"; one day in Austin)
- Chicago (27 hour trip on Amtrak "Texas Eagle"; transfers back to Milwaukee and Madison)
- Milwaukee
- Madison
This was in July 2001, but as far as I know the routes are all the same.
The total distance was 6,326 miles, and it was a 14-day trip in all.
That's a lot of time on the train, but that was the point: I had friends to visit in each of the stops, but along the way I wanted the scenery. The "Coast Starlight" route in particular was really amazing, but traveling through the Upper Midwest, including Glacier National Park, along with the desert Southwest, was also really interesting too.
I booked the ticket by phone, and the ticket cost $382.20 (coach seating), which was a steal compared to what it would have cost to fly or drive. The ticket had to be completely planned out in advance, but could be changed for a $30 fee, if there were seats available. It was called the "All Board America" fare.
"Seven Great Reasons to Take a Train" (Longer article I wrote for adventure travel magazine "Blue" in 2002, with longer descriptions of different routes): http://www.bluemagazine.com/main.cfm?inc=article&chid=1&artID=6
"Off Track" (Longer article I wrote on lack of Amtrak funding for Salon.com after the 9/11 attacks): http://archive.salon.com/tech/feature/2001/11/21/amtrak/index.html