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.

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I'm based in Urbanna, just 15 miles west of Deltaville on the Rappahannock. This past year, we cruised for about 10 days,in early October, starting out from Urbanna to D'ville. 2nd day, D'ville to Mobjack, 3rd day, Mobjack to Yorktown 5th day, Yorktown to Hampton, Day 7 Hampton to Cape Charles, Day 9, plan was Cape Charles to Deltaville, but we got caught in a storm, and had to be towed to Horn Harbor with engine problems. Day 12, I singlehanded to Urbanna, a 9 hour leg in weather, mostly motoring. All of the other legs were close hauled or beam reaches. We attempted to make each leg about 6 hours, leaving an anchorage around 9 am, and arriving at the next by 3, or 4 pm. We had an alternative plan to sail north, if the wind was blowing that way but luckily, we were able to sail our original route.
Sail with my brother on his 423 Beneteau "Breezing Up", annually over Memorial and Labor Day Weeks, out of Tide Water Marina, Baltimore. Been to all the locations mentioned including attending the annual Annapolis Yacht Sales' Beneteau Rendezvous in 2010 Deltaville, 2009 Camp Lett, Rhode River, 2008 Deltavile, 2007 Solomon Island. Looking forward to possible DelMarVa circle sail in the near future. Brother has "6 Pack" USCG license for inland waters, and would like to gain certification for open waters. We are hoping this will supply some of the sea time required.

Personally like the "Back Door" to St. Michael's on Santa Domingo Creek, Choptank River. Creek is narrow, but good anchor holding at the last marker in the creek. About a mile to a dhingy dock on the back side of St. Michael's.

Another personal favorite is Annapolis anchoring off the Naval Academy Practice Field. As we are members of the Fleet Reserve Association, we are able to use the dinning facilities of the Fleet Reserve Club next to the Marriott to enjoy the same boat scenes on "Ego Alley" and the music the Marriott guest do, lol.

Give us a hail on VHF Channel 16 then to 68 to meet up if out during the period.


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