Best Restaurants in Annapolis

Annapolis might not be a large city – even as the state capital, only about 40,000 people live here – but it is home to a surprising number of fabulous fine dining restaurants, cozy cafes, and delicious local eateries. No matter if you come for the peak of Maryland Blue Crab season in July or for the sailboat and yachting festivals in summer and fall, there is always something delicious on the menu in our charming city. Read on to learn about the best restaurants in Annapolis!

Fine Dining With a View

For perhaps the best food and certainly one of the best views anywhere in Annapolis, head to the Chart House on 2nd Street. Located in a renovated historic boathouse, the dining area features floor to ceiling windows and spectacular views of the mouth of the Spa Creek, the Severn River, and Chesapeake Bay. Come for their popular happy hour (4:30-7pm, Sunday-Friday), come to sample the freshest seafood in the city, or come to watch the sailboat races in May and the boat show in October. It doesn’t matter when you visit, just make sure you do!

Carrol’s Creek Café, overlooking the Annapolis Yacht Basin, is another excellent choice for fine seafood, tasty steaks, and fresh local ingredients. Have dinner overlooking the river, relax in their iconic lounge, and enjoy the laidback elegance of this local favorite since 1983.

Local Favorites

Looking for Annapolis restaurants that are more casual and cozy than chic? What could be better than a popular watering hole in the old city jail? Visit the Dock Street Bar and Grill for classic cocktails, a fun ambience, craft beers, and delicious local seafood and “classic grub.” Obviously, try the crab dip, the crab cakes, and the crab cake sandwich, or just go all out with the Crab Cake Dinner for two. Looking for a delicious brunch? Locals swear by the Iron Rooster, a quaint eatery on Market Space where breakfast is available all day long. Go nuts with chicken and waffles, try one of their Eggs Benedict recipes, or pig out with steak and eggs and mimosas. If it is date night, visit Vin 909 Winecafe for an incredible medley of flavors and a wide selection of fresh seafood, meat, and vegetarian dishes.

Get a Taste of Our City at Annapolis Restaurants

There are far too many incredible Annapolis restaurants to name here, but ask a local or any of our resident experts and we will be happy to steer you to something delicious. With the Chesapeake Bay in our backyard, there is never a shortage of delicious seafood dishes, no matter where you go.

And don’t forget to fully get the most out of your Annapolis stay by booking yourself one of our vacation rentals!

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