So many places, so little time.
🙂 So many choices. There is such a wide array of kinds of spots, its hard to say where to begin. You have pristine unspoiled low country / tidewater places along the Eastern Shore from mid-Bay and south. You have more developed towns and marinas. You have an endless choice of dock bar / tiki bar spots if that's your thing. Lots of wide choices from the top of the Bay to the bottom.
Since you are driving down from NYC, my instinct is to recommend you put the boat over on Kent Island, which would be both one of the fastest places to get to by car from that direction, and its fairly centrally located. Head down the NJ Turnpike to the end, cross into DE onto I-95, then take SR1 south. Pick up Rt 301 south through the rest of DE and into MD and it takes you to Kent Island. When I drive south on that route I have no trailer and am doing it "briskly"
🙂 and can make that drive in well under 4 hrs. Feel free to drive as fast as you dare UNTIL you hit the MD line, then do not drive more than 10 over the limit since the cops are active and keep speeds well in check.
Its a short hop down to St. Michaels, a beautiful harbor town, great shops for the Mrs. and lots of dining choices. A maritime museum to tour. Beautiful anchorage, and some marina choices. Its upscale money out of DC.
Its a short hop to Annapolis across the Bay.
On Kent Island there is a score of dock bars and restaurants. Lots of choices.
Up the Bay you have Rock Hall. Fairlee Creek. Worton Creek. Sassafras River is beautiful. Chestertown is well up the Chester River, and historical (brick streets, very old homes).
Skip Baltimore. Its simply a dangerous town. One of the murder capitals in the country. I can say some nice things too, but with so many other great choices, why bother with anything remotely dicey.
I have not been to Herrington Harbor marina (either one, and there are two) but hear great things. Its on the Western Shore.
Many make Solomons Island a destination.
If you want quiet nature, that's a different topic. Not sure what you are looking for.
The Bay in that timeframe can be dead flat, or rough. The basics apply: when the wind opposes the tides and current is where and when it gets rough. The two biggest rivers that empty into the Bay are the Choptank and Potomac, and the Bay can give you some exercise in their mouth in bad conditions. But generally nothing to worry about.
Take thunderstorm warnings seriously.
Bugs can be bad. AC can be your best friend. Anchorages are not deep, and the bottom is usually mud. Many marinas have a pool and some bar / restaurant on-site or nearby.
Here's a few basic links.
https://chesapeakebaymagazine.com/
https://www.chesapeakeliving.com/
http://upperbayboating.com/
https://www.spinsheet.com/
Feel free to fire questions. If I know, I'll share. Reasonably current on some of it, and never been to some of it. Its a pretty big place.