Annapolis

Davis' Pub

Eastport · Annapolis · American pub fare

The Lazy List

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

Spa Creek · Annapolis · Seafood / Steak

The Reliable

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

Towne Centre Area · Annapolis · Wine Bar / Mediterranean

The Rager

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.

Red Red Wine Bar

Upper Main Street · Annapolis · Wine Bar / Bistro

The Wild Card

Red Red Wine Bar is a genuinely fun, accessible spot if you go in knowing what it is: a bubbly-forward wine bar built for socializing and sharing flights, not deep-dive cellar exploration. Send your friend here for a casual night out — just don't send them expecting a sprawling wine list.

Reynolds Tavern (Tea & Wine)

Church Circle · Annapolis · Tavern / Afternoon Tea

The Wild Card

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

Eastport · Annapolis · Seafood / Raw Bar

The Reliable

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

Eastport · Annapolis · American Cafe

The Wild Card

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.

Paul's Homewood Cafe

West Annapolis · Annapolis · Greek and American, Steakhouse

The Reliable

Paul's isn't a wine destination, but it's also not trying to be — and the Wednesday half-price bottle program turns a reliable neighborhood dinner into a genuinely smart night out. Bring someone you like, order the moussaka, and let Wednesday do the work.

Reynolds Tavern

Church Circle / Historic District · Annapolis · Historic Tavern / British-Inspired

The Reliable

Reynolds Tavern won't win any wine awards, but it earns its keep — fair prices, a few genuinely interesting picks, and a list that respects the food on the menu. Send a friend here for the atmosphere and tell them to order the Châteauneuf.

Firebirds Wood Fired Grill Annapolis

Riva Road / Annapolis · Annapolis · American, Steak House, Seafood

The Reliable

Firebirds Annapolis is a reliable wine program doing exactly what it's designed to do: give a broad crowd recognizable bottles at prices that won't cause a scene when the check arrives. Come on a Monday, order the J. Lohr, and you'll have nothing to complain about.

Blackwall Hitch Annapolis

Eastport / Waterfront · Annapolis · Seafood-focused American

The Reliable

Blackwall Hitch isn't a wine destination, but it's a solid, unpretentious list at fair prices with one genuinely great weekly deal. Show up on a Wednesday, split a bottle of something decent, and watch the harbor — that's the play.

Smashing Grapes Annapolis

Annapolis Towne Centre Area · Annapolis · Mediterranean-inspired American

The Reliable

Smashing Grapes is a dependable wine stop in Annapolis — not thrilling, but not lazy either. For a neighborhood wine bar, the Neyers selections alone give you enough reason to show up; just don't expect the by-the-glass program to keep up with the room's ambitions.

Red Red Wine Bar + Bistro

Downtown / Main Street (Upper Block) · Annapolis · Wine Bar & Bistro — American and Italian-leaning comfort food

The Reliable

Red Red Wine Bar is the kind of place Annapolis needs more of — a genuinely wine-forward spot with a list long enough to reward some exploration. The markups take a bite and the staff won't blow your mind, but for a downtown pour before or after a night on the water, this is your spot.

Cooper's Hawk Winery & Restaurant – Annapolis

Annapolis Towne Centre · Annapolis · Modern American

The Reliable

Cooper's Hawk Annapolis is exactly what it is — a well-run, corporate winery restaurant where the wine list exists entirely in-house and the experience is built for people who want wine to be easy, not educational. Send your parents here without hesitation; send your wine-obsessed friend somewhere else.

Vin 909 Winecafé

Eastport · Annapolis · Farm-to-table American and wood-fired pizza

The Wild Card

Vin 909 is the kind of neighborhood spot that makes you feel like you found something. The list is small but honest, the prices are fair, and a few bottles — especially the Eyrie and the Txacoli — have no business being this accessible. Yes, send a friend here for wine.

Carrol's Creek Cafe

Eastport / Spa Creek Waterfront · Annapolis · Contemporary American and Seafood

The Reliable

Carrol's Creek isn't a wine destination, but it's a genuinely good place to drink wine — especially on a Tuesday when the list goes half-price and the harbor view is free. Show up, order the Sonoma-Cutrer with your crab cakes, and enjoy the fact that not everything has to be complicated.

Ruth's Chris Steak House Annapolis

Festival at Riva / Riva Road · Annapolis · Steakhouse

The Reliable

Ruth's Chris Annapolis is a reliable option if you want a familiar, well-executed wine list to go with a serious steak — just don't come looking for discovery or value. The markups are steep, the list is corporate, but the wines are legitimate and the storage is sound.

Cafe Normandie

Downtown / Main Street · Annapolis · French Bistro

The Reliable

Cafe Normandie isn't a destination for wine geeks, but it's a genuinely solid neighborhood French spot where the list won't embarrass you. Order the Alsatian Riesling, lean into the Loire, and let the kitchen do the heavy lifting.

Luna Blu

West Street Arts District · Annapolis · Italian / Mediterranean

The Reliable

Luna Blu isn't a destination wine list, but it's an honest one — Italian-focused, fairly priced, and well-matched to the food coming out of the kitchen. Send a friend here and tell them to skip the Santa Margherita.

Grapes Wine Bar

Annapolis · Annapolis · American, French

The Reliable

Grapes is exactly what Annapolis needed — a wine bar that takes California and France seriously without taking itself too seriously. No fireworks, no surprises, but a reliably good bottle and a room worth lingering in.

Lewnes' Steakhouse

Annapolis · Annapolis · Steak house

The Rager

Lewnes' is the kind of steakhouse wine list that actually earns its Best of Award of Excellence — deep California roots, serious ceiling bottles, and a Wednesday half-price night that's practically a civic service. The markups are steakhouse-steep across the board, but if you navigate smart, this is one of the better bottles-with-beef experiences on the mid-Atlantic coast.