If you're in the Yorktown area, you should definitely spend a night in Sarah's Creek and eat a gourmet dinner at the River's Inn. You can anchor in the creek or take a slip in the marina. From there, up to Mobjack Bay, and anchor out in the East River or the Severn River. Then to Jackson Creek (Deltaville), and then over to Onancock on the Eastern Shore. Back south to Cape Charles. The winds that time of year are usually southerly, unless a front is coming through, so going back south can be a chore. Add a bit of time for getting back south.