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Driving from Orlando to NYC via the Carolinas

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My husband and I (from Australia) are planning to drive from Orlando to NYC (to Washington with train to NYC) in April this year. I would be interested in ideas of towns and cities to visit and stay overnight and good/interesting BBs to stay in. Our budget is medium to good!

How long should we allow - two weeks? Longer?

Is it feasible to take a detour to Kentucky?

I would be grateful for any ideas!

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