Recommendations for Annapolis and Navy/Air Force game Oct 4

Depending on how much extra time you are going to have, you might want to check out Kent Island, a few miles east across the long, long bay bridge.

This short scoping (real estate) video might give you some ideas of what you might like to research further over there if anything perks your interest:

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It's said Nap Town is a drinking town with a sailing problem. That gives them too much credit, maybe, but it's a fun place. Harry Browne's is a good, white-linen restaurant on Capitol circle. It's fun to hang around by the dock to see who's coming in or going out. Depending on time of year, some decent sized yachts are in port. They're either moving South or North, but several are local, anyway, and the "scene" is fun to watch. There's a hotel bar right on the dock (but I can't remember the hotel...sorry). Galway Bay for an Irish pub. Over in Eastport (across the bridge) from downtown Annapolis, try Davis' Pub (crab cakes), Boatyard and Blackwall Hitch. Or, Lewnes Steakhouse. Ram's Head can have live music, but check their schedule. There are others, of course. Shopping is a mix of nautical-themed and USNA tourist-y stores. Few chain stores, which is refreshing. There's a nice HellyHansen and, IIRC, Musto (or equivalent) for sailing gear. Re-used sail tote bags are plentiful. There's not a big swath to cover, and it'll take just a couple of hours to go through those. There's a USNA welcome center, but I don't know if they do open tours any longer. Check with them. Your concierge ought to also be able to give you a couple of ideas, along with newer options that I may not be aware of.

If you're looking for a day trip, consider a drive over to St. Michael's on the Eastern Shore. The Inn at Perry Cabin is special (and worth it). We go once or twice a year to have lunch on the back patio. St. Michael's also has little art galleries and a nice walking downtown.

CW