I would add a few favs we visit...
Western Shore:
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Rhode River, the weekends can be busy but during the week it should be pretty quiet. The Smithsonian owns much of the land around it. Note High Island is now gone pretty much, just watch your chat

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Solomons, Zanihizers or Spring Cove if you want a marina. Zans has moorings of your prefer. The Calvert Maritime Museum is wonderful
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St. Leonard Creek, past Solomons up the Patuxent. You will see for yourself
Eastern Shore:
The Wye, shouldn't be missed, Dividing Creek is a favorite spot. Great to explore by dingy as well. You could spend several days here.
St. Michaels, the Maritime Museum is a great time. Some good restaurants. Splurge for a night at The Inn at Perry Cabin
Oxford, the more laid back and less commercial version of St. Michaels. Anchoring off the public beach is where we usually end up.
If you think you'll go North of Annapolis...Still Pond, Worton are worth the extra distance. With 4'6" draft you could try sneaking into Still Pond Creek, but the entrance is tricky. Fairlee Creek is worth it off season. Let us know if you want more info