Richard, my advice is quite a bit different...
...but I'm basing my advice on the assumption you would like the entire trip to be an enjoyable one. (You OTOH may have posed the question because you can't get away until October...it's hard to tell).IMO, leaving in October (from Maine) is way too late; you'll have to deal with autumnal storms and be forced to consider more day hops in lieu of offshore runs, which in turn will slow you down, which just further compounds the problem. Moreover, another trend you'll be fighting the entire trip is the shortening day - especially significant when you start running exclusively in the Ditch and need the daylight to pilot safely. You have the option of sailing LI Sound but from exiting NY Harbor down to the Virginia Capes you have few all-weather harbors along the way if you stay outside...so a stable wx pattern for a few days will be a big help in making progress if you plan offshore runs then.I don't see tropical storms figuring into your planning at all, as they march up the East Coast well past the time you should have left. You'll just have to deal with the arrival of a tropical storm as does anyone else migrating down the East Coast; fortunately, f'casting occurs well in advance of their arrival and you can be conservative in arranging your routing to be tucked in acceptably before any storm might arrive. If you were headed for Bermuda, it would be a different story...The Chesapeake is a national treasure and a natural wonder and it would IMO be a shame for you to pass it up by sailing offshore in that stretch. In fact, I would suggest your two criteria for scheduling your passage should be: 1) time the route so you have mostly pleasant weather for the entire run...and 2) provide sufficient time on the Bay as you pass thru to at least enjoy a few special locations on both Western & Eastern Shores.Having said all that (and having done the ditch a few times now) I'd recommend departing Norfolk by mid-September. You'll be chased by fewer fronts when initially crossing the large, shallow estuaries in VA and NC, you'll have more daylight to work with when ashore exploring or trying to make miles on the boat, and the temps will range from warm but humid to brisk but refreshing. (Don't forget the bug screens, and be sure they are No-See'um screen material, if you can). There should be no ski hat weather, which is not the case when leaving the Bay in October.Allowing for two weeks of daysailing on the Bay suggests an arrival at the C&D around Labor Day, which has you enjoying warm weather and minimal frontal systems while sailing down the coast in August. How long it takes to reach Florida is a function of how many roses you stop to smell along the way.Of course, everyone has their own view on this and we don't know what kind of boat you have - if it's got an inside steering station, then some (but not all) of my reasoning isn't suitable for your circumstances. But assuming you've got a typical open cockpit, I think both you and the Mate will find things a lot more enjoyable - and less hurried - if you try to keep yourselves in the belt of pleasant autumnal weather that slowly sinks down the eastern seaboard.Jack