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Roadtrip Across the Country

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Hello!
I've recently completed a few shorter roadtrips (All departing from Toronto, Ontario and going to places such as Virginia, Kentucky, and Florida). I'm graduating university shortly and have managed to save up some money by staying home through school, and would like to do a trip across the United States and Canada. I have created a detailed budget and am working on my itinerary. I have 180 days, leaving June 2 and returning home on December 2. We want to hit every single state (exception of Hawaii...We plan on Alaska though) and every province/territory except for Nunavut (difficult to access).
If anyone has any suggestions for routes, cities we don't want to miss, things that are must-dos, scenic by-ways...pretty much anything..please comment and let me know.
Open to any and all suggestions (there are four early-20s going).
Thanks! :)

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