All really good info but here's my two cents. If you mean to make time than the 24/7 nature of going outside can't be beat. Once you round Cape Charles your next only dependable stop is OC, MD. That said the tide running out can be fierce so you need to time things well in a displacement boat. Next stop if you must is Cape May than Atlantic City than Sandy Hook. But again I stress the value in going outside is you can easily run 24/7. The sea tends to flatten at night as an added benefit.
If you have the time than of course cruise the Chesapeake. If you want to you can run inside 24/7 as well but just make sure to time your arrival at Ready Point with high tide. You will have the tide all the way to Cape May. Skip going back in and run the NJ shore straight through. If you leave pre-dawn out of Cape May (easy to do as the inlet is big) than you will make Sandy Hook before sunset or just at.
