The mid Summer Chesapeake has winds more like Long Island with temperatures a little warmer and higher humidity. The places to anchor and enjoy are the same, it's just not as comfortable for most people outside. It's not that there aren't GREAT DAYS, it's just that you're as likely from Mid-June through August to have are real Summer-time experience. (We used to go out, decades ago ;^))), regardless and seem to tolerate the humidity and higher temperatures. Now, unless you have AC to take a break with, its not quite the same.)

The best general sailing, touring and anchoring is probably May to mid-June; and after Labor Day through October. You can sail with a little heat April through sometime in November.

The beauty of the Chesapeake (expecially with a draft of less than 5') is that you can enjoy so many different places to anchor and not be crowded. There are little towns (expecially if you're used to Connecticut or New York) to explore.

If it were me, supposing to be you, I would probably bring your boat down in late March or early May. Then spend a couple or three months doing 3 and 4 day cruises -- with a few longer ones. You'll be able to see a bunch of places. I'd be glad to discuss it with you, if you wish.