I would invest in a Chesapeake Bay Cruising Guide put out by Chesapeake Bay Magazine. It will provide a ton of information about more places than you can visit. As a cruising guide I think it is one of the best prepared guides you can buy for any place. Get one now and start looking. It covers the water
and the land. It's thick and has nice birds eye sketches for getting into the places you really want to be in. That adds a little more comfort as you sneak into shallower waters. You just need to deal with the idea that 6 ft of water
is more than enough. Not much for rocks to hit. Most of the bay is less than 6 ft deep.
Getting back into places takes some help from a guide and it's what you really want to do the most. You'll find a sail straight down the Bay affords little to see as you stay offshore
quite far. 5 Ft draft
gets you into nearly all the important places. You need to plan on going to them as they don't jump out at you. A lot of locations have significant historical features on land and so study where you can get ashore to see some of the many. Once you get south of the Potomac
the density of boats drops a great deal. Most of the area is more wild and you'll find fewer boats in the anchorages
Sept / October is the tail end of hurricane
season and while getting one would be rare, the left over tropical storms are more common and still something to watch out for. The mouth of the Potomac
can make it's own weather
and in severe weather
caution is urged. The southern bay in a blow can stand up 6 to 8 feet and I've seen 10ft. Steep chop is common once winds get over 25 to 30 knots.
I take a flexible approach and being opportunistic about where it is easy and have alternates if things change. Plot as many potential spots and you can before you leave. You might do only some of them but keeping options open takes best advantage of weather and places worth seeing. You can do a few north / south treks with proper winds and still see things when it suits your fancy. If you study charts
close you'll see places where you can get back in quite far. Those would be worth exploring.
We sail out of the York River on the fat end of the Bay. The Mobjack is a favorite since on the 4th of July you can get a quiet anchorage with few other boats. I like a lot of the northern points too. I also like the side creeks at the lower Potomac in MD and VA and some selected spots on the eastern shore.
Personally, I would avoid north of the Potomac til after Labor Day. Until labor Day you can expect poor winds and high heat / Humidity. Sept to early November is what I consider prime time. Most of the boats are not out as much and you'll find easier access to prime spots in the northern bay. You have enough time to see a lot of places but I doubt you can see them all. My approach to sailing here is take off from a spot and see where you can get to. Plan up all the possible places you might want to go and go to the ones that sail the best. Zig zag across the bay and pay attention to the large void in the middle. Many of the eastern rivers afford a long way into the the interior
and and in the fall can be a nice pleasant trip.