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The 10 Best Wine Bars in Annapolis

The 10 Best Wine Bars in Annapolis

In the capital city of Maryland, you’ll find beautiful views of Chesapeake Bay, historic buildings, and what most people don’t know, an incredible wine scene.

The Best Wine Bars in Annapolis

Carpaccio Italian Kitchen + Wine Bar

Upscale Italian dining with a focus on delicious wine. Here you’ll find a comfortable ambiance with a full menu offering authentic Italian cuisine.

To pair with the delectable fare, you’ll find a sprawling wine list. Full of selections from California, Tuscany, and New Zealand, along with other notable growing regions.

Quite a few are available by the glass, with certain selections only available for purchase by the bottle.

When the menu becomes too overwhelming, knowledgeable staff are there to help. Plan your next date night at Carpaccio for an unforgettable experience.

  • Location: 1 Park Pl, Annapolis, MD 21401

Cooper’s Hawk Winery

This winery houses its own label wines served alongside upscale American fare. You’ll find a full tasting room dedicated to the love of great wine.

The list includes reds, whites, rose, sangria, and dessert selections. Staff is friendly and always available to offer recommendations and answer questions.

Their tasting room creates a relaxing and comfortable environment no matter your wine-drinking experience.

This is the perfect place to grab dinner and start the night right with a glass or two.

  • Location: 1906 Towne Center Blvd, Annapolis, MD 21401


This unique location houses and combines bakers, baristas, a pastry chef, and a sommelier to create an all-in-one cafe and wine bar.

No matter the time of day, you’ll find something you love. Not only do they offer delicious pastries, bread, and coffee, but their wine list is just as impressive.

The 2nd Wednesday of the month is when they host a tasting and pairing with their own pastries and hand-selected wines.

They offer a few flight options to make your own tasting at any time. Or browse their wonderfully curated wine list full of growing regions around the world.

No matter what you pick, it’s sure to please.

  • Location: 141 West St, Annapolis, MD 21401


This casual yet bohemian restaurant and bar brings a luxurious feel while offering a menu inspired by European cultures.

The food menu is seasonal and includes both specialty and local products made to delight. The drink menu includes cocktails, beer, and of course, wine.

Nearly everything can be purchased by the glass, with a few high-end exceptions only available by the bottle.

Growing regions from across the globe are featured, including France, Spain, CA, OR, and even South Africa, to name a few.

You won’t regret a trip to Flamant for your next wine night out.

  • Location: 17 Annapolis St, Annapolis, MD 21401

Grapes Wine Bar

Designed to be a destination for those who love food and wine, Grapes doesn’t disappoint.

Here you’ll find weekly rotating selections and a cozy place to enjoy great wine with friends, old or new.

You’ll find that all the selections on their list are available by the glass or bottle. Each is hand-chosen by expert staff.

The best part is every wine served is available for purchase right next door.

Along with a large selection of domestic options are varieties from Italy, France, and Australia, to name a few.

  • Location: 1410 Forest Dr, Annapolis, MD 21403


At Level, you’ll find small plates designed for socializing and pairing with their hand-crafted cocktails or curated wine list.

Within the red, white, bubbly, and rose options are a few offered by the glass, but all can be purchased by the bottle.

California dominates the list alongside a few other popular growing regions.

There’s a daily happy hour offering discounts on wine certain wine selections, and making it a perfect place for a weeknight drink.

Dedicated to seasonal farm to table plates, there’s always something delicious to pair a glass of wine with at Level.

  • Location: 69 West St, Annapolis, MD 21401

Red Red

Chic and bohemian describe this wine bar located in downtown Annapolis.

This will be your new destination for eclectic eats and an unpretentious environment to enjoy wine.

On their menu, you’ll find over 40 selections available by the glass and 110 wines by the bottle. You’ll also find pre-built flights with cheeky names.

All are designed to delight and introduce you to wines you may not see elsewhere.

To make this location even more unique is the fact that their by-the-glass selections are available on tap. Enjoy this one-of-a-kind experience for your next wine night.

  • Location: 189 B Main St, Annapolis, MD 21401

Smashing Grapes

This isn’t your average wine tasting. Currently, a reservation is required, and we recommend you make one ASAP.

Here you’ll find a relaxing and welcoming environment for all. Outdoor seating on the patio offers a cozy place to curl up around the fire while sipping on a glass of wine.

The wine list doesn’t disappoint either, with 350 selections to pick from, the options seem endless.

Their menu is split by red or white and then into new and old-world selections.

But be sure to also check out their organic wines, and don’t forget about the rare and unique section, either.

No matter what you’re looking for in a glass of wine, you’ll find it at Smashing Grapes.

  • Location: 177 Jennifer Rd, Annapolis, MD 21401

Vin 909 Winecafe

Here you’ll find fine selections of pizzas, full plates, and an impressive wine list. You’ll find selections that highlight regions around the world.

They focus on curating a welcoming environment that almost feels like home, a place you’ll come back to over and over again.

The staff is friendly and can offer knowledgeable information about both the cuisine and wine served.

Enjoy a wood-fired pizza that pairs perfectly with a bottle of Syrah or Malbec while relaxing outside on their patio.

This is one place you will come back to again and again.

  • Location: 909 Bay Ridge Ave, Annapolis, MD, 21401

49 West

Inspired by a European coffeehouse, you’ll find community paired with great food and drink, all housed in one location.

You’ll find live music nightly, which highlights the best of the local music scene in Annapolis.

Being a full coffeehouse and wine bar, you can start or end your day at 49 West. The wine list includes a wide range of selections from worldwide growers.

No matter your wine-drinking experience, 49 West is a great place to grab a drink with friends and enjoy a true taste of Maryland.

  • Location: 49 West St, Annapolis, MD 21401

Final Thoughts

No matter the reason you’re in the capital of Maryland, the wine bars will have you coming back for more.

Make sure you add these great locations to your itinerary for your next visit. You won’t want to miss the best of the wine scene in Annapolis.