Red Red Wine Bar

Davis' Pub is a great place to drink — just not wine. The list is inoffensive and priced fairly, but it exists as an afterthought in a place where the real action is cold drafts and steamed crabs. Order the Brancott if you must, then pivot to beer.

Chart House Annapolis is a reliable wine list in a genuinely great setting — you'll drink well enough, but you're paying for the view as much as the pour. Go in with eyes open on the markup and lean on the California stalwarts that earned their spots here.

Smashing Grapes is quietly one of the better wine programs in the mid-Atlantic, operating in a market that doesn't always demand it — which makes it even more impressive. Send a friend here, absolutely, and tell them to skip the safe picks.

Reynolds Tavern is the kind of Wild Card that earns its badge by being completely sincere — a 275-year-old tavern that stocks Vieux Télégraphe and Maryland Albariño without making a big deal about it. If you're in Annapolis and skipping wine here in favor of a generic hotel bar down the street, that's on you.

Blackwall Hitch isn't a wine destination, but it's a reliable spot to drink something decent without getting gouged — especially during happy hour. Send a friend here if they want a glass on the water, not if they're chasing something to talk about.

Eastport Kitchen isn't a wine destination, but it's also not pretending to be one — and for a casual neighborhood café in Annapolis, the wine program punches well above its weight class. The markups are mostly reasonable, the by-the-glass selection is genuinely broad, and if you know what to order, you can drink pretty well with your burger.