Sip, Savor, Repeat: Unearthing the Best Annapolis Drinking Spots

If quality drinks with friends is something you enjoy, you’ve come to the right city. Annapolis has a robust drinking culture that has earned it the nickname “a drinking town with a sailing problem”. We’ve helped you narrow down the choices with our list of the top five places to go drinking in Annapolis.

Image courtesy of Davis’ Pub

1. Davis’ Pub

This little Eastport watering hole has been serving the Annapolis community in some form since the 1920s, and has operated as Davis’ Pub since 1986. For decades, this eclectic dive bar has been a favorite among locals for their outstanding pub fare and lively atmosphere. We’ve put Davis’ in our FLOHOM Voyager’s Guide twice because it really shouldn’t be skipped!

Favorite drink: Orange or Grapefruit Crush

400 Chester Ave.
Open Sun – Thur: 11a–10p | Fri & Sat: 11a–12p

Image courtesy of Forward Brewing

2. Forward Brewing

This “nano-brewery” is on a mission to offer a fresh and local product that Eastport and Annapolis can call its own. They work to advance the community by honoring its history and offering a gathering place, while using forward-thinking methods in everything they do. Forward has quickly become a community favorite with their positive energy, delicious craft beer selection, and tasty light fares.

Favorite drink: Dry dock beer

418 Fourth St.
Open Tue – Thu: 4p-9p | Fri: 12p-9p | Sat: 11a-9p | Sun: 11a-8p

Image courtesy of Pusser’s Caribbean Grille

3. Pusser’s Caribbean Grille

Since 1994, this little slice of the Caribbean has been one of Annapolis’ favorite watering holes. Located in the Annapolis Waterfront Hotel, their dock bar is an unmissable summertime experience and truly a rite of passage when visiting the city. Named for the Caribbean rum, their painkillers are a delicious entrance to a relaxing time on the water.

Favorite drink: Signature painkiller. Our tip? For a light buzz, go with #2. For an immediate buzz, try #5 (our favorite).

80 Compromise St.
Open: Mon – Fri: 7:30a-12a | Sat & Sun: 8a-12:30a

Image courtesy of Dock Street Annapolis

4. Dock Street Bar and Grill

 Dock Street Bar and Grill has been a downtown Annapolis favorite for over a decade. Their extensive offerings of food and drink, combined with their friendly environment and welcoming staff has solidified their status as a go-to haunt for locals. It’s our favorite bar for late-night fun— watch the second floor transform into a club at night on the weekends!

Favorite drink: Tito’s vodka & soda

136 Dock St.
Open Tue & Wed: 4p-2a | Thu – Sun: 11:30a-2a

5. Great Frogs Winery 

This family owned vineyard just outside of downtown is a lovely location that frequently holds fun community events and tours. Their grapes are grown and handled with the utmost care to produce fine wines that showcase the versatility in the Chesapeake Bay region. Try some of their award winning varieties on their rustic country style property with ample indoor and outdoor seating for the perfect wine tasting experience.

Favorite drink: Cold Blooded 20 – 60% Cabernet Sauvignon X 40% Syrah blend

3218 Harness Creek Rd.
Open Fri: 5-8p | Sat: 11a-5p

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