I am very active in cruising the Chesapeake Bay. We are berthed in Rock Hall, MD in Osprey Point Marina and sail the upper and middle bay. Typically, we do a one week cruise in June and another in September.Timing of which weeks you choose and your ideas on how much water to cover shape and control the voyage.
We have done the hard itinery routine; Annapolis, Solomon's, St. Mary's, Tangier Island, Onacock, Solomons, Rock Hall and there is usually more motoring than sailing.
We have also started by going to a region like the Choptank River and then spent 3-4 nights in anchorages off the Choptank and sailed 80% of the time and been on less rigid itinery schedules.
We tend to go south from Rock Hall as we can cover Annaoplis, Baltimore, St. Michaels, the Chester River, Magothy River, Rhode River, and points north on weekend trips.
I would be very interested in folks that are based in the Solomons, Potomac, Deltaville and points south as what they choose to do for week long cruises.
Your thoughts please, we would all enjoy some favorite anchorages and I would share any that I am requested to expound on.