Moved to Annapolis last year after dreaming of moving here for about 20 years. It probably would not make your list because it is expensive, but it is much cheaper than where I lived in Montgomery County.
The Pros are outstanding though:
Chesapeake Bay (we live on the water, which is sweet)
More history than most places in America (founded 1640)
Home of the US Naval Academy (something awesome about seeing all of these great young leaders)
Awesome weird mix of being more conservative than some parts of MD but also being more bohemian and accepting. People are more into outdoor living, navy football, etc compared to how much you make.
People wear topsiders (don’t you dare call them Sperrys) not to be trendy, but because you need positive traction on boats. Same for Helly Hansen and similar brands.
I can be in DC for meetings in 45 mins.
Delicious, delicious crabs.
Victoria, BC
West Chicago, IL
