Give it a chance
There would not be nearly so many sailboats and racing events (international, national, local) hosted on the Bay if wind conditions were generally underwhelming. We've sailed the Bay 20 years. Yes, the hottest times of year tend to have less constant winds and even turn still for a while, and my advice for you on that is three-fold:1) Make sure you have a good engine and prop on your sailboat in fine working order. When winds die, we quite happily turn our sailboat in to a "trawler" and cruise at 7 knots under power, especially if we need to make a destination. Although we prefer to sail, there's a lot of people out there that do nothing but power-boat all the time (gosh!) You can do either if so equipped. Main thing is enjoy the Bay. 2) In the Annapolis area, winds in the hot months often pipe up in the late afternoon and evening, like they did yesterday and Sunday afternoon. Plan to sail accordingly especially since it stays light until late.3) The further south we go on the Bay, the better chance we have of finding wind since the Bay is more open. One of the best seasons we've had was the one we spent out of Deltaville (Rappahanock River area).