Go on a winery and brewery tasting
Annapolis has both, after all, which means we like them twice as much. Great Frogs Winery on Harness Creek Vineyards has been around since 1999, but just opened its tasting room two years ago. Visit the winery to walk the grounds, explore the old tobacco barn, and do a tasting ($25, reservations requested). And on the last Friday of the month, from May through September, Great Frogs hosts its Date Night Series, where couples can enjoy music, pizza, and wine. For hops enthusiasts, there’s Chesapeake Brewing Co. of Annapolis. The beer is brewed across the Bay in Crisfield, but Annapolis is home to the pub, which opened this year. The brewer is a graduate of the U.S. Naval Academy, so there’s a Beat Army Golden Lager on tap at the bar. The brewing company also hosts the Annapolis Crab, Crash & Cruise every first and third Sunday of the month from June through September, one of the best date nights in the state. Feast on steamed crabs, fried chicken, corn, beer, and Smith Island cake (that's the Maryland state cake, because they have one of those), then cruise the Annapolis Harbor at sunset.