Out of the way....
Chicago typical tourist locations (The Shed is wonderful, one of the best ones besides ones on the NE) Science museum is also great
Burbon trail in KY
Tail of the Dragon
Philly typical tourist stuff
Going east I dont think there is much in my opinion. Done that route couple dozen times. Check with some of the PCA chapters for the major towns you will be hitting, they will know the best roads to have fun on.
Unfortunately you will most likely run into rain for most of the trip depending on how far south you go due to the hurricane so might not get much top down weather.
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2000 Boxster Tiptronic
2003 Boxster
2003 996 C2 Cab
2002 996 (SOLD)
1986 944 (gone but missed)
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