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2 Week Road trip From Seattle to KY Need Help with Timing

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In July a buddy and I are flying out to Seattle to start a 2 week road trip that ends in Louisville, KY at a 3 day festival. Our ideal scenario would have us see the Redwoods/Yosemite while making our way down to the Grand Canyon/Yellowstone and back up through Utah, over to Colorado on up to South Dakota/Mount Rushmore, checking out various sights/natural wonders and maybe some whitewater rafting along the way. Mount Rushmore we would either drive straight to Louisville Ky for a 3 day music festival or are thinking of flying to save the drive time.

My main concern is, with only 12 full days between the start of the trip and the start of the festival, do we have a chance of completing our trip or should we reconsider some options? I really don't want to shortchange ourselves but our window is really only the 12-14 days. Should we think smaller? Or is this doable?

Thanks for any help you can offer!

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