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East Coast Driving Trip August 28th-September 6th

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I am looking for suggestions of must sees and advice for this 10 day driving trip. The 10 days include the time it will take to travel to the first stop, as well as, the drive home.
So here's the rundown:

There will be 4 women on this trip, 2 in their mid-twenties, and 2 in their early 50's. On this girls road trip we will be traveling from Kentucky, through West Virginia to get to our first destination somewhere along the coast of Virginia. Here is a list of cities in order to let you know the gist. Please let me know if this is not doable in your opinion and what we might want to skip. Also, if you have any cities that are a must along the New England coast that are must sees advise of those as well.

Cape Charles, VA
Ocean City, MD
Ocean View, DE
Washington, DC
Philadelphia, PA
Atlantic City, NJ
New York, NY
Bridgeport, CT
Charlestown, RI
Jamestown, RI*
Salem, MA
Newburyport, MA
Portsmouth, NH
York Harbor, ME
Kennebunkport, ME*
Marlboro, VT
*Where there are multiple cities listed we may not actually stop in both it is just to keep us going along the coast.

Any advice on lodging prices and tips for that time frame would be appreciated. Also some of the best places to eat. We love antiques and shopping. The only part of the trip I'm not sure about is DC and Philadelphia. There is a lot of history in both places and I'm not sure if it will cut too much into the time we have available. We plan on spending maybe 1 day in Atlantic City because 2 of the people in our party like to gamble.

The main goal of this vacation is to take in georgous views, enjoy some great food, and each others company. We hope to spend as little time on the interstates as possible for the drive up but we want the fastest route home possible so we can make the most of our road trip.

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