Skip the dry walking tours and hit a pub crawl instead. The Tipsy History tour actually makes learning about the 1700s bearable while you drink. If you prefer low-key, grab an outdoor painting session by the water; it beats staring at plaques for three hours. Spend half a day wandering the brick alleys, but keep it moving before the cruise ship crowds descend. Grab a crab cake and leave the heels at home, these sidewalks hate shoes.
Address: Annapolis, Maryland, 21401
Curated experiences in Annapolis Historic District
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