I have single-handed this several times. It is an overnight sail for me, stopping in Little Creek just inside the Bridge-Tunnel, maybe not that much more than a day sail for you. It can be a little bouncy off the mouth of the Delaware depending on the tide, but not bad. I always stop at Vinings Landing Marina in Little Creek, it has a better staff than the other marinas in town, and, is right down the street from Captain Groovys, one of my favorite places to eat on the east coast. Oyster bar and seafood restaurant with a very friendly staff, the parking lot is always full with local cars. The T shirts aren't bad either.
Since I am usually on my way south, my next stop is Norfolk/Portsmouth. Portsmouth has a historic district with a lot of nice older houses, Norfolk has some nice places to eat and a couple nice museums. Or you can head for Jamestown/Williamsburg or further up the bay. You won't see it all in one summer, but I will leave the details to those more familiar with the bay.