I have known people who’ve lived aboard at Anchorage, Harborview, Henderson’s Wharf, Oasis Lighthouse Point (formerly Baltimore Marine Center), and Maryland
Yacht Club (well outside the city but still on the Patapsco) at various points over the past 10 years. However, it seems their liveaboard policies are quite changeable year to year so the only way to know anything for sure is to contact the marinas directly.
At the Anchorage, I’m not sure renting
a slip directly from an owner gets you around the liveaboard restrictions, at least not officially. So feel that one out carefully.
The city marinas are all gated and have security
so there’s never been a high incidence of on-premises crime at any of them. It’s really your comfort level with what goes on beyond the gates. I haven’t been downtown much since COVID hit, so I don’t have a sense of where things are going with crime.
That aside, if I didn’t need to be in Baltimore and wanted to live aboard on the Chesapeake in a place that’s a bit lively in the winter, I’d probably look at Annapolis
for its strong cruiser/liveaboard community or Hampton for being slightly more moderate in winter climate than the mid-bay.
Some posters have mentioned the eastern shore, and you could lump in Solomons and Deltaville on the western shore as places that would have similar vibes to some of the eastern shore locales. This might be OK with you, but be aware they are all going to be extremely sleepy in the wintertime, sometimes with boater-oriented restaurants, bars, shops, etc. closing seasonally.