Sorry, there used to be sunsail charters that operated out of Annapolis
Landing Marina, which then switched to moorings I believe, but they went out of business because too few people came to the bay to maintain operations. The problem with Chesapeake sailing is four fold, it's very busy with other boats in the commercial
channel and all of the one design races they have, it has ubiquitous crab pots in the entrance of every river, during the summer it can be extremely hot without wind
and last it really has no public beaches that you can anchor
off and go ashore (and you really wouldn't want to swim most places). It is nice for finding an anchorage, surrounded by houses typically and going into a small quaint town for dinner via dingy. Free dingy docks at most towns and lot's of little places to gunk hole. I lived here for 15 years, maybe I'm jaded. The catamaran
company here in annapolis
had a bunch of used multihulls that owners would rent out, but it wasn't the nice fleet of moorings.