Since my Bay experience and knowledge is dated to say the least I would appreciate current info and recommendations on available charters, destinations, anchorages, restaurants (with dockage ?) etc.
August isn't the best time of year but you don't have to worry about being cold. The wind
can be a bit wanting in August though last year was not really that bad. All the charters are northern bay. There are enough decent places to go so at least you can motor
around and have a fun time. Given the distance is about 250 nautical miles north to south you won't run out of room or places to go. We live down on the fat end of the bay and it's pretty much plenty of room to anchor
at all the the good places even 4th of July. You just have to get this far south.
Charters should be wide open and Annapolis is probably a good place though the north end has a lot of charter
operations too. A good resource would the Chesapeake Bay
Magazine web site. The have a full listing of a lot of the resources you might want. The Chesapeake Bay
Cruising Guide would be a worthwhile investment since if you sail by the wind
you get you can catch as catch can and have the best information no matter where you end up. For August I would suggest you take that approach. There are far more places you could go than you can go. If you want to sail then be flexible!
So what is it you like to do and things you expect to find?