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Road trip - Bmore - Charlottesville, va - Richmond - Jamestown ....

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Hi, I'm taking my mother on a road trip for a week. The current plan is the following:
Baltimore
Charlottesville, VA to see Monticello, Montpelier and Monroe's house
Richmond, VA
Jamestown
Williamsburg
Yorktown
Ocean City, MD
St. Michaels
Chestertown
Baltimore

Obviously this is too much. How should we do a circle to start and end in Baltimore. Monticello is the one place we don't want to miss.
Thanks!

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