Since I work in Wilmington, Northeast is even closer for me. I had not previously considered the Northeast river because that part of the Bay looks too shallow north of Turkey Point. But after looking at the chart again, there looks to be a couple miles of sailable water north of Carpenter Point. So you could do short sails in the river itself, or motor the 6 miles down the channel past Turkey Point for a full day and/or weekend, right?
For reasons that I don't fully understand, the North East River seems to be secret to people in the Philadelphia metropolitan area. North East has a great crabhouse ("Woody's") where cold beer and hot crabs make a great end of a day on the water. However, the area doesn't get a lot of press, so a lot of people don't realize that the depth is not as much of an issue as it may appear. It really is the closest direct access to the Chesapeake. If you look at the charts, there are some well delineated areas that are shallow. My former boat (Cal 25) had 4' draft, and I could sail pretty much all around the North East River. My current boat draws 5'8", and there are some areas that I avoid at low tide. However, I never felt that draft was much of a problem. The shallow areas are well marked on the charts, and it is easy to pick a course for a daysail that avoids them. The prevailing winds blow out of the Southwest, so we typically have a nice close-hauled course down Turkey Point, and return on a broad reach/run. It makes for great daysailing. The river is actully quite wide, so I don't feel "constrained" when we daysail.
As far as overnighting is concerned, we motor or sail (depending upon the wind) down Turkey point and the Upper Bay is right there. We typically take short overnight cruises down to Still Pond or the Sassafrass. St. Michaels/Baltimore/Annapolis can be done in a day, but it is a longer haul to get down there.
If/when you decide that you want to keep your boat on the Chesapeake, I would definitely recommend you consider North East. It may or may not be right for you, but it is close. Shoot me an email off line if you ever want to come down and take a look at our club. The are also several other marinas in the area, so we are not the only game in town.