Most of Eastport (Back Creek) and Spa Creek (Eastport to the South and historic Annapolis to the North) are in reach of some restaurants.
I agree with svquintana about Eastport Yacht Center. Kim Brown will get you sorted. I lived there for two years.Small working yard, no weekend hours. (410) 280-9988 Easy walk to Davis' Pub and to Leeward Market and longer walk to Boatyard. Rather a long walk for my taste downtown but easy dinghy
range and there are water
taxis in season.
Watergate Pointe is lovely. It's an apartment complex where a marina happened. No services beyond water
. Easy walk to Adam's Ribs, Eastport Kitchen, and VIN 909. not bad to downtown or Eastport restaurants. (855) 507-0387
Mears Marina is rather expensive but lots of resort services. Bert Jabins and Port Annapolis are good but on the awkward side of the creek without ground transportation or a good dinghy. They are the easiest walk to groceries. I prefer Jabins to Port A but YMMV.
If your boat
is small enough AND you have yacht club reciprocity look at Eastport Yacht Club. (410) 267-9549
Look at South Annapolis Yacht Centre (410) 263-1643. They are in the midst of reconstruction but the location is hard to beat other than being above a drawbridge.
Also check Spinsheet (local sailing rag) and, while you are in town, the bulletin board at Giant Food
Store for private slips. Look for Severn House in particular.