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I bought a car in CT and took the auto train from Washington DC area to Sanford FL. It wasn't too bad. Back then I was a smoker and spent a lot of time talking with the other smokers/watching movies in the smoker car, staring out the window, playing games/puzzles.
Back then my family would do long road trips and wed be driving like 8 - 12 hours to see family so, for me, it was like that but more spacious and I could smoke lol.
Maybe if the auto train works with wherever you want to go and you don't mind using up your miles you could have your car when you get off, then drive back, maybe do a scenic thing with stops or something.
Good luck with your trip.
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