Come down the Bay, go outside and run up to the Delaware, take the C-Peake/Delaware canal back over to your point of origin. Then maybe make another run outside down to North Carolina and come back up. If you have run into any problems, then you can come back up inside the ditch and get back up the bay to Annapolis. Then, you may be ready to run up to Maine and back. Do you plan on shooting across to England, or over to Lisbon and then up the coast to the UK? Running across from the mouth of the Bay to Bermuda, Azores and Cannaries at least gives you a few spots to pull in and rest, replinish your rum supply and get support if need be.