Looking out from the Thomas Point Shoal Lighthouse
You really can't leave a port city without looking at some of its lighthouses if they still exist.
Three-hour long tours to the remote Thomas Point Shoal Lighthouse (built in 1875) are organized through the Annapolis Maritime Museum.
You'll first have to take a 30-minute boat ride 1.5 miles offshore through choppy seas, transfer to the lighthouse dock, then climb up a steep ladder through a small hatch onto the deck.
Oh, and there are no toilets on the boat or at the lighthouse so you may want to handle your business before you depart.