Mall gouge
The Annapolis Mall, or "Westfield ShoppingTown Annapolis," is on West St. and Bestgate Rd., only a few minutes from downtown. There are other shopping areas. Has a movieplex, all the usual stuff.
Further out, there is Arundel Mills Mall, you can google it, about 20 minutes away.
Since plebes are with parents, the liberty limit isn't looked at closely. They will find you, escape with you in your car, and no one thinks you really going to take them drinking in Baltimore in civilian clothes. Baltimore and DC metro areas are about right. Allow plenty of time to get them back, because everyone else will be doing the same thing.