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wrote:

We expect to be in Chesapeake Bay for 2 or 3 weeks starting mid-October
or thereabouts. Other than obvious choices like Annapolis and Solomons
Island, I'm looking for good places to hang out during the week.
Priorities are something like this:

1. Good WiFi service.

I don't know any particular ways to get this unless you are in a
marina that has it. IME the wi-fi may reach out to your boat at the
dock, but not out to an anchorage. The Deltaville Marina off Jackson
Creek has wi-fi out to the docks, and they have a ride in to several
restaurants in town. As does Dozier's Point in Broad Creek (the other
side of Deltaville (both wi-fi and restaurants)

2. Good storm protection.

3. Room to anchor, and/or moorings with launch service.

Deltaville has a good protected anchorage off the Piankatank behind
Stove Point Neck in Fishing Bay, but AFAIK, no moorings or launch
service. I think you can get a ride to restaurants in town from there
though.

Off the Potomac on the Maryland side, the St. Mary's River (Horseshoe
bend) has a good anchorage, but absolutely no services whatsoever
including no restaurants.

Smith Creek, off the St. Mary's River has good protected anchorages,
and there are several restaurants available by dinghy, but no
groceries or services unless you go in to Pt. Lookout Marina (our
home marina) which has a pool and laundry facilities.

Mill Creek off the Patuxent back of Solomons is a good protected
anchorage, and Solomons has lots of restaurants and grocery stores.
On the other side of the Patuxent, Cockrell Creek is a good protected
anchorage opposite Blackstone Marina, but no services there except to
go by dinghy to Clarke's Landing Restaurant.

4. Availability of groceries, laundromats, restaurants, etc.

On weekends priorities change with WiFi becoming less important, and
more oriented towards interesting places to be. All suggestions
gratefully appreciated...

Not in any order:

We found Chestertown to be an interesting town to visit, but while
there are restaurants there, my husband found the grocery stores near
the docks to be to expensive (gourmet foods). When we were there,
there was no internet service. May have changed.

Baltimore is also an interesting place to visit, and there are some
anchorage places in there, particularly behind Fort McHenry. I've
only been there in a marina. I wanted to anchor and go up to the top
of the Trade Center and take a picture from there of the boat
anchored, but chickened out. Places to visit include the National
Aquarium, the Inner Harbor, the Maryland Science Center, Oriole Park
etc.

Crisfield has a nice little harbor, and a LOT of restaurants. The
marina is a municipal marina and charges way more for weekends than
during the week, so it pays to go during the week - also the museum is
open then but don't go Monday - most everything is closed. They have
a little trolley thing that will take you out to where the grocery
store is.

Shaw Bay (back of St. Michaels) is a very nice protected anchorage.
Horseshoe Creek is also, although sometimes crowded on weekends.
Neither have any services to speak of.

If you anchor near the ferry dock in Oxford (but the holding isn't
very good there), you can dinghy in to the shore and either walk to
restaurants or some of them will come and pick you up if you call.

If you can find your way in without going aground on the sand bar,
there is a nice protected anchorage in Selby Bay, but on weekends
there is sometimes music from shore. No services, although there is a
marina there (no transients) that has fuel and pumpout.

Reedville (if you can stay upwind of the menhaden plant) has a nice
little museum, a lot of Victorian homes, and some restaurants.

Tangier Island is one of a kind. It is possible to anchor there, but
I wouldn't. The marina isn't that expensive. Lots of restaurants.
Smith Island too, but I've never been there because we've always been
afraid of running aground.

The marina in Indian Creek (Chesapeake Bay Boat Basin) used to give
you a lift to town to a restaurant but they no longer do that. We
haven't yet gotten to the Yeocomico or Onacock. Or to St. Michaels
either, come to that.

grandma Rosalie