Annapolis, Maryland is a rich city full of rich history and beautiful views. However, one of the most important parts of vacation is the food! Whether you’re looking for a relaxing dinner on the waterfront or a hole-in-the-wall place away from the crowds, here’s a few restaurants to check out while in the city.

Boatyard Bar & Grill:

This waterside seafood joint was the only Annapolis restaurant to be included in Baltimore Magazine for their famous crab cakes. Open from 8 am to midnight every day, you can enjoy their delicious, fresh food at any time during your stay. Not a seafood fan? Not to worry, their hamburgers are also voted the best on the bay! This is really a can’t miss place!

Annapolis Ice Cream Company

This is the only ice cream shop in historic Annapolis that makes its ice cream in the store! With all natural ingredients, your sweet tooth will not be disappointed. And the critics agree — they’ve been voted “Best of Annapolis” eight years in a row!

Carpaccio Tuscan Kitchen

An Italian restaurant with a cozy atmosphere complete with fountains and soft evening light, the menu is full of both classic and innovative Italian dishes. The staff is consistently described as “friendly without being overbearing”, and locals insist you try the cucumber cocktail!

Chick and Ruth’s Delly

If you’re looking for something unique in the heart of the city, this is the place to go! With fast service and generous portions, it’s hard to go wrong at this American-style diner. A family owned restaurant with delicious milkshakes, you get a small town feel when you eat here that’s hard to come by in such a bustling city.

Light House Bistro

Not only is this place unique for its food, but also its mission! This bistro takes people who have graduated from the community’s Homeless Prevention Support Center, and helps them get on the job experience to be able to gain experience and continue their progress towards a career. All profits are invested back into the program, which means you can enjoy an incredible meal and help the community! Whether you order one of their delicious veggie omeletts or meatloaf and mashed potatoes, it’s hard to go wrong.

Vin 909

This restaurant/winery is the perfect place for any occasion. They don’t take reservations, but it’s hard to complain about the wait when they let you order drinks and sit in their beautiful garden while they get your table ready. Their brick oven pizza is a favorite among regulars and you can’t go wrong with any of their dessert choices. 

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