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ideas 4-5 day mini road trip around DC

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HI, My hubby is in DC for work and my daughter and I have tagged along for a trip. We have been to DC before a couple of times but have never ventured out of the city before. We are now planning to do just that after his work winds up and so we will have 4/5 day mini-vacation together over the Memorial w/e.

We are thinking it would be nice to spend some time getting a flavor for the area but we'd like to focus on the coast as we miss the sea and thought about driving out toward Chesapeake Bay and from there going on to a beach town. Do you have any recommendations of a nice laid back places to visit, for a family, but not too crazy e.g. few college students. We'd like to stay somewhere upscale, pref. with a pool but that allows kids (many inns don't sadly). We've previously visited places in New England like Cape Cod (and MV), Cape Ann (Gloucester, Rockport, Ipswich etc), Maine (Kenebunkport, Camden) and wondered if there are similar places in Maryland/Virginia/Delaware/general DC surrounds where we can experience NE-style beach towns with funky boutique shops and enjoy great seafood.

If we are completely off chart please tell us as another option was to go slightly further afield (DH fancies returning to the Outer Banks-- is Norfolk, VA similar?). Is it a mistake to rule out the many quaint towns in Virginia (Alexandria, Culpeper etc? What are the main to-dos for this area?

Any advice would be appreciated. Many thanks!

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