The City Dock area of downtown Annapolis floods fairly frequently, even at high tides when the wind is right; it is very low. The saving grace is that the surrounding areas rise quickly from the level of the bay; Main Street, which runs from city dock to the state Capital Building, rises very quickly; a reasonably steep but short walk.

Business owners in the area immediately adjacent to the docks are practiced in sand bagging and pumping out the stores. Most are owned by family's that have been in business there for many many years.

This area has been a port since the 1700's. Remember Alex Haley and Kunta Kinte? There is a monument at dock street where he (Kunta Kinte) landed.

So, it all depends on the details; I would expect some flooding, but anything less than, say, 2-3 feet, will be taken in stride. It would have to come up a great deal to damage too many business. However, the businesses mentioned in the article, Armadillo's and Storm Bros. Ice Cream Factory are right at the Dock and are in the line of fire so to speak. BTW, Storm Brothers is an old fashioned ice cream parlor and a short walk from the Navel Academy. A national resource. Been there many times. Try their Pistachio ice cream. (no association, just a frequent customer!)

Isabel did produce a fairly high surge, and did cause some damage, but downtown recovered very quickly.