Reviews of the 10+ best restaurants in Annapolis, MD

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Embark on a culinary exploration of Annapolis, where gastronomic delights await at every turn. In our meticulously curated reviews, we unveil the essence of the city’s dining scene, presenting the 10 Best Restaurants in Annapolis. These establishments have been carefully selected for their exceptional culinary offerings, inviting atmospheres, and dedication to providing an unparalleled dining experience. Whether you’re a local connoisseur or a visitor eager to savor the finest flavors the city has to offer, our guide is your gateway to the culinary gems that define the phrase “Best Restaurants in Annapolis.” Join us as we navigate the epicurean landscape of this charming city, where each restaurant is a testament to the vibrant and diverse culinary tapestry that Annapolis proudly presents to discerning palates.

The 10 best restaurants in Annapolis

Chick & Ruth’s Delly:

Chick & Ruth's Delly in annapolis
Chick & Ruth’s Delly in annapolis

Address: 165 Main St, Annapolis, MD 21401

Phone: (410) 269-6737

Operating Hours: Monday-Saturday: 6:30 AM – 8 PM; Sunday: 7:30 AM – 8 PM

Reviews: 4.5/5 on Yelp, 4.7/5 on Google, 4.2/5 on TripAdvisor

Must-Try Meals: Pastrami Sandwich, Corned Beef Sandwich, Brisket Sandwich

Average Cost: $10-$20 per person

Website: https://www.chickandruths.com/

Menu: https://www.chickandruths.com/menu/

A Classic Jewish Deli Experience:

Located in the heart of historic Annapolis, Chick & Ruth’s Delly is a beloved institution that has been serving delicious deli food since 1965. This family-owned restaurant, named after its founders, is known for its warm and welcoming atmosphere, reminiscent of old-fashioned diners. The walls are adorned with photos of local celebrities, politicians, and military personnel, giving the place a sense of nostalgia. The friendly staff adds to the charm, making you feel like a regular even on your first visit.

A Menu Full of Deli Delights:

Chick & Ruth’s Delly is famous for its sandwiches, and for a good reason. The portions are generous, and the ingredients are fresh and flavorful. Their pastrami, corned beef, and brisket are cooked to perfection and served on soft and chewy rye bread. Each bite is a mouthful of deliciousness, and you will be hard-pressed to find a better deli sandwich in town. Make sure to try their homemade potato salad and pickles, which are the perfect accompaniments to their savory delights.

An All-Day Breakfast:

If you are craving breakfast at any time of the day, Chick & Ruth’s Delly has got you covered. Their all-day breakfast menu includes traditional favorites like omelets, pancakes, and French toast, as well as unique offerings like crab cakes Benedict and chicken and waffles. Pair it with a cup of their freshly brewed coffee or a refreshing mimosa, and you have the perfect start to your day.

The Tradition Continues:

In addition to being a popular dining spot, Chick & Ruth’s Delly is also known for its tradition of reciting the Pledge of Allegiance every morning at 8:30 AM. This tradition started back in 1989 and has been followed ever since. Visitors can join in on the pledge and receive a free slice of apple pie as a token of appreciation. This adds to the overall warm and welcoming atmosphere of the restaurant, making it a must-visit spot in Annapolis.

Boatyard Bar & Grill:

Boatyard Bar & Grill in annapolis
Boatyard Bar & Grill in annapolis

Address: 400 4th St, Annapolis, MD 21403

Phone: (410) 216-6206

Operating Hours: Monday-Sunday: 11 AM – 10 PM

Reviews: 4/5 on Yelp, 4.5/5 on Google, 4.3/5 on TripAdvisor

Must-Try Meals: Crab Cake Sandwich, Rockfish Tacos, Steamed Shrimp

Average Cost: $20-$30 per person

Website: https://www.boatyardbarandgrill.com

Menu: https://www.boatyardbarandgrill.com/dinner-menu

A Waterfront Dining Experience:

Situated along the picturesque Annapolis waterfront, Boatyard Bar & Grill offers a delightful blend of casual dining and stunning views. As you enter the restaurant, you will be greeted with a warm and inviting ambiance, with nautical-themed decorations and a cozy fireplace. The expansive deck overlooking the harbor is the perfect spot to enjoy a meal while taking in the sights and sounds of the bustling marina.

Fresh and Local Seafood:

Boatyard Bar & Grill takes pride in using fresh and locally sourced ingredients, especially when it comes to their seafood offerings. Their crab cakes are a must-try; made with jumbo lump crab meat, they are known for their generous size and mouthwatering flavor. Other popular seafood dishes include rockfish tacos and steamed shrimp, both bursting with flavors and perfectly cooked. For non-seafood lovers, the restaurant also offers options like burgers, salads, and sandwiches.

A Selection of Craft Beers:

In addition to its delicious food, Boatyard Bar & Grill also boasts an impressive selection of craft beers. With over 100 beers from local and international breweries, beer enthusiasts will have plenty of options to choose from. Don’t forget to try their famous “Dirty Oar Lager,” a collaboration between Boatyard Bar & Grill and Fordham Brewing Company, which is exclusively available at the restaurant.

Live Music and Events:

Apart from its beautiful location and delicious food, Boatyard Bar & Grill also hosts live music events throughout the year. From local bands to national acts, the restaurant offers an enjoyable and lively atmosphere for music lovers. They also host special events, such as their “Thursday Night Wine Dinner Series,” where they pair delicious food with unique wines from around the world.

Carrol’s Creek Cafe:

Carrol's Creek Cafe in annapolis
Carrol’s Creek Cafe in annapolis

Address: 410 Severn Ave, Annapolis, MD 21403

Phone: (410) 263-8102

Operating Hours: Monday-Sunday: 11 AM – 10 PM

Reviews: 4/5 on Yelp, 4.5/5 on Google, 4.3/5 on TripAdvisor

Must-Try Meals: Crab Cakes, Lobster Bisque, Grilled Caesar Salad

Average Cost: $30-$50 per person

Website: https://carrolscreek.com/

Menu: https://carrolscreek.com/lunch-menu

A Fine Dining Experience:

Located in Eastport, just a short walk from downtown Annapolis, Carrol’s Creek Cafe offers a sophisticated dining experience with breathtaking views of Spa Creek. The elegant interior, with its white linens, soft lighting, and stunning artwork, creates the perfect setting for a romantic dinner or a special occasion. The restaurant also has outdoor seating, which is ideal for enjoying the view during warmer months.

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An Award-Winning Menu:

Carrol’s Creek Cafe is renowned for its award-winning menu featuring fresh and locally sourced ingredients. Their crab cakes are a must-try, made with jumbo lump crab meat and served with roasted red potatoes and vegetables. Other popular dishes include their lobster bisque, grilled Caesar salad, and seared scallops. Each dish is beautifully presented and bursting with flavors, making it a feast for both the eyes and taste buds.

A Wine Connoisseur’s Paradise:

With over 400 wines from around the world, Carrol’s Creek Cafe boasts an extensive wine list to complement their exquisite food offerings. The restaurant also has a full bar, serving handcrafted cocktails and local brews. Their knowledgeable staff can help you pair the perfect wine with your meal, making it a complete dining experience.

Private Events:

Carrol’s Creek Cafe offers private event spaces for special occasions, such as weddings, rehearsal dinners, and corporate events. The main dining room and patio can accommodate up to 150 guests, and the private dining room can host up to 30 guests. With stunning views and exceptional service, Carrol’s Creek Cafe is the ideal venue for a memorable event.

Miss Shirley’s Cafe Annapolis:

Miss Shirley's Cafe Annapolis in annapolis

Address: 1 Park Pl, Annapolis, MD 21401

Phone: (410) 268-5171

Operating Hours: Monday-Friday: 7 AM – 3 PM; Saturday-Sunday: 8 AM – 3 PM

Reviews: 4/5 on Yelp, 4.6/5 on Google, 4.4/5 on TripAdvisor

Must-Try Meals: Chicken and Waffles, Fried Green Tomatoes Benedict, Crab Cake Sandwich

Average Cost: $15-$25 per person

Website: https://www.missshirleys.com/

Menu: https://www.missshirleys.com/menu/

A Southern-Inspired Brunch Spot:

Miss Shirley’s Cafe Annapolis is a popular breakfast and lunch spot known for its southern-inspired cuisine and charming atmosphere. The restaurant pays homage to its namesake, Miss Shirley McDowell, who was a beloved cook in Baltimore during the 1960s. The interior of the cafe is bright and colorful, with whimsical décor, creating a fun and relaxed ambiance.

Must-Try Brunch Favorites:

Brunch lovers will be in for a treat at Miss Shirley’s Cafe Annapolis, with a menu filled with delicious and creative dishes. Their chicken and waffles dish is a favorite among regulars, featuring golden fried chicken tenders served on top of homemade waffles and drizzled with sweet maple syrup. Another must-try is their fried green tomatoes benedict, which combines southern and classic eggs benedict elements for a unique and flavorful dish. Don’t forget to try their famous crab cake sandwich, served with crispy fries and coleslaw.

A Kid-Friendly Menu:

Miss Shirley’s Cafe Annapolis is a family-friendly restaurant, offering a special menu for kids under 12. The “Little Shirley’s Brunch” menu features kid-sized portions of popular breakfast and lunch dishes, such as pancakes, French toast, and grilled cheese. They also offer fun and interactive dishes like “create your own sundae” and “build your own taco,” making it a hit with the little ones.

An Award-Winning Restaurant:

Miss Shirley’s Cafe Annapolis has been recognized by various publications and organizations for its exceptional food and service. It has been featured in Baltimore Magazine’s “Best Breakfast Spot” and “Best Kid-Friendly Restaurant,” and was named one of the “Top 100 Brunch Restaurants in America” by OpenTable. With its warm and welcoming atmosphere, delicious food, and accolades, Miss Shirley’s Cafe Annapolis is a must-visit spot in the city.

Osteria 177:

Osteria 177 in annapolis
Osteria 177 in annapolis

Address: 177 Main St, Annapolis, MD 21401

Phone: (410) 267-7700

Operating Hours: Monday-Sunday: 5 PM – 10 PM

Reviews: 4.5/5 on Yelp, 4.7/5 on Google, 4.5/5 on TripAdvisor

Must-Try Meals: Lobster Ravioli, Veal Medallion, Risotto

Average Cost: $30-$50 per person

Website: https://www.osteria177.com/

Menu: https://www.osteria177.com/menu/

An Upscale Italian Restaurant:

Osteria 177 is a fine dining restaurant specializing in modern Italian cuisine. Located on Main Street, the restaurant offers an elegant and intimate setting for a special occasion or a romantic dinner. The interior is beautifully decorated, with warm lighting, white linens, and comfortable seating. The knowledgeable staff adds to the overall dining experience, making it a top choice among locals and visitors.

Authentic Italian Fare:

The menu at Osteria 177 features classic Italian dishes with a modern twist. Their lobster ravioli, made with fresh Maine lobster meat, is a popular dish among diners. Other must-try items include their veal medallion, served with wild mushrooms and Marsala wine sauce, and their risotto, which changes daily depending on the seasonal ingredients. Pair your meal with a glass of wine from their extensive wine list, and you have the perfect Italian dining experience.

Private Dining:

Osteria 177 offers two private dining rooms for events and special occasions. The “Carmine Room” can accommodate up to 16 guests and features a fireplace, while the “Francesca Room” can host up to 40 guests and has its own bar. The restaurant also offers customized menus for these events, creating a unique and personalized dining experience for guests.

Wine Dinners:

For wine lovers, Osteria 177 hosts monthly wine dinners, featuring multi-course meals paired with wines from different regions of Italy. This is a great opportunity to try new dishes and expand your knowledge of Italian cuisine and wines. The restaurant also offers occasional Cooking classes, where guests can learn how to make some of their favorite dishes from the menu.

Buddy’s Crabs & Ribs:

Buddy's Crabs & Ribs in annapolis
Buddy’s Crabs & Ribs in annapolis

Address: 100 Main St, Annapolis, MD 21401

Phone: (410) 626-1100

Operating Hours: Monday-Thursday: 11 AM – 9 PM; Friday-Sunday: 11 AM – 10 PM

Reviews: 4/5 on Yelp, 4.3/5 on Google, 4.1/5 on TripAdvisor

Must-Try Meals: Jumbo Lump Crab Cakes, Smoked BBQ Ribs, Cream of Crab Soup

Average Cost: $20-$30 per person

Website: http://www.buddyscrabs.com/

Menu: http://www.buddyscrabs.com/menu/

A Waterfront Seafood and Barbecue Restaurant:

Situated on the bustling Main Street, Buddy’s Crabs & Ribs offers a casual dining experience with stunning views of Ego Alley. The restaurant is known for its seafood and barbecue dishes, making it a top choice for those looking for a taste of Maryland’s signature cuisine. The interior is cozy and inviting, with a full bar where you can enjoy a refreshing cocktail or a cold beer while waiting for your table.

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Fresh and Local Seafood:

Buddy’s Crabs & Ribs takes pride in using fresh, local, and sustainable seafood in their dishes. Their jumbo lump crab cakes are a must-try, made with the highest quality crab meat and minimal filler. Other popular seafood dishes include their steamed shrimp, crab dip, and creamy crab soup. For non-seafood lovers, the restaurant offers mouthwatering smoked BBQ ribs, served with homemade sauces and sides.

Happy Hour Specials:

If you are looking to unwind after a long day of exploring Annapolis, Buddy’s Crabs & Ribs has got you covered with their happy hour specials. From Monday-Friday, 3 PM – 7 PM, enjoy discounted drinks and appetizers at the bar or on the outdoor deck. The crab dip and buffalo shrimp are popular choices among happy hour goers.

Live Music:

Buddy’s Crabs & Ribs hosts live music every Friday and Saturday night, featuring local bands playing a variety of genres. With a relaxed atmosphere, great food, and live music, this is the perfect spot to spend your evenings in downtown Annapolis.

O’Learys Seafood Restaurant:

O'Learys Seafood Restaurant in annapolis
O’Learys Seafood Restaurant in annapolis

Address: 310 3rd St, Annapolis, MD 21403

Phone: (410) 263-0884

Operating Hours: Monday-Sunday: 11 AM – 10 PM

Reviews: 4/5 on Yelp, 4.4/5 on Google, 4.2/5 on TripAdvisor

Must-Try Meals: Cream of Crab Soup, Oyster Po’ Boy, Seafood Nachos

Average Cost: $20-$30 per person

Website: http://www.olearysseafood.com/

Menu: http://www.olearysseafood.com/menu.html

A Casual Seafood Spot:

O’Learys Seafood Restaurant is a casual dining spot located in Eastport, just a short walk from downtown Annapolis. The restaurant has been serving delicious seafood dishes since 1983, making it a favorite among locals and visitors alike. The interior is simple and laid back, with nautical décor and large windows that provide plenty of natural light.

Delicious Seafood Dishes:

O’Learys Seafood Restaurant offers a wide selection of seafood dishes, including steamed crabs, oysters, andmussels. Their cream of crab soup is a popular choice among diners, made with lump crab meat and served with fresh bread. For a more filling option, try their oyster po’ boy or seafood nachos, both packed with flavor and generous portions.

Daily Specials:

In addition to their regular menu, O’Learys Seafood Restaurant offers daily specials that feature seasonal ingredients and new dishes. These specials are listed on their website and social media pages, so be sure to check them out before your visit. You never know what delicious surprise you might find.

Private Dining:

O’Learys Seafood Restaurant has a private dining room that can accommodate up to 50 guests for special events and parties. The room features a private bar and personalized menus, making it the perfect spot for celebrations or corporate events.

Vin 909 Winecafé:

Vin 909 Winecafé in annapolis
Vin 909 Winecafé in annapolis

Address: 909 Bay Ridge Ave, Annapolis, MD 21403

Phone: (410) 990-1846

Operating Hours: Tuesday-Saturday: 12 PM – 10 PM; Sunday: 11 AM – 9 PM

Reviews: 4.5/5 on Yelp, 4.7/5 on Google, 4.5/5 on TripAdvisor

Must-Try Meals: Wood-Fired Pizza, Charcuterie Board, Mushroom Risotto

Average Cost: $20-$30 per person

Website: http://www.vin909.com/

Menu: http://www.vin909.com/menu.html

A Cozy Wine Bar and Cafe:

Located in Eastport, Vin 909 Winecafé is a cozy and intimate spot that serves delicious food and an extensive selection of wines. The interior is warm and rustic, with brick walls, wood accents, and soft lighting. The restaurant also has a lovely outdoor patio, perfect for enjoying a meal on a nice day.

Wood-Fired Pizza:

Vin 909 Winecafé is known for its wood-fired pizzas, made with fresh and seasonal ingredients. The dough is hand-stretched and topped with flavorful combinations, such as the “Roasted Wild Mushroom” or the “Fig and Prosciutto.” Pair your pizza with a glass of wine from their carefully curated list to enhance the flavors.

Charcuterie Board:

For those looking for a lighter option, Vin 909 Winecafé offers a selection of charcuterie boards that feature premium cured meats, cheeses, and accompaniments. Create your own board by choosing from their list of meats and cheeses, or go for one of their pre-selected options like the “Italian Board” or the “French Board.”

Mushroom Risotto:

Another popular dish at Vin 909 Winecafé is their mushroom risotto, made with wild mushrooms, Parmesan cheese, and truffle oil. This creamy and flavorful dish is perfect for vegetarians looking for a hearty meal. The restaurant also offers other vegetarian and vegan options, making it a great choice for those with dietary restrictions.

Lewnes’ Steakhouse:

Lewnes' <strong data-lazy-srcset=
Steakhouse in annapolis" width="960" height="640" /> Lewnes’ Steakhouse in annapolis

Address: 401 Fourth Street, Annapolis, MD 21403

Phone: (410) 263-1617

Operating Hours: Monday-Sunday: 5 PM – 10 PM

Reviews: 4.7/5 on Yelp, 4.8/5 on Google, 4.6/5 on TripAdvisor

Must-Try Meals: Filet Mignon, Lobster Bisque, Key Lime Pie

Average Cost: $50-$75 per person

Website: http://www.lewnessteakhouse.com/

Menu: http://www.lewnessteakhouse.com/menu/

A Classic Steakhouse:

Lewnes’ Steakhouse has been a staple in Annapolis for over 20 years, serving high-quality steaks and seafood to its loyal patrons. The interior is elegant and sophisticated, with dark wood accents, white linens, and soft lighting. Its prime location in the historic district of Annapolis and its reputation for excellent food and service make it a top choice for special occasions.

Perfectly Cooked Steaks:

Lewnes’ Steakhouse takes pride in the quality of their steaks, which are hand-selected and aged in-house. Their filet mignon, served with a red wine demi-glace, is a favorite among diners. For seafood lovers, the restaurant offers delicious options such as the pan-seared scallops and the lobster bisque, made with chunks of fresh lobster meat.

Extensive Wine List:

With over 300 bottles to choose from, Lewnes’ Steakhouse has an extensive wine list that features selections from all over the world. Their knowledgeable staff can help you find the perfect pairing for your meal, making the dining experience even more enjoyable.

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Outdoor Dining:

During the warmer months, Lewnes’ Steakhouse offers outdoor seating on their patio, providing a charming and intimate atmosphere. This is a great option for those looking to enjoy a delicious meal while taking in the sights and sounds of downtown Annapolis.

Dock Street Bar & Grill:

Dock Street Bar & Grill in annapolis
Dock Street Bar & Grill in annapolis

Address: 136 Dock St, Annapolis, MD 21401

Phone: (410) 268-7278

Operating Hours: Monday-Sunday: 11 AM – 2 AM

Reviews: 3.5/5 on Yelp, 4.1/5 on Google, 3.5/5 on TripAdvisor

Must-Try Meals: Crab Dip, Fish Tacos, Maryland Crab Soup

Average Cost: $15-$25 per person

Website: http://www.dockstreet-bar.com/

Menu: http://www.dockstreet-bar.com/menu.html

A Lively Sports Bar:

Dock Street Bar & Grill is a popular spot among locals and tourists for its casual atmosphere, delicious food, and live music. Located on the waterfront, the restaurant offers spectacular views of the harbor and is a great place to catch a game or enjoy a night out with friends.

Maryland Favorites:

Dock Street Bar & Grill features classic Maryland dishes, such as their famous crab dip, made with real lump crab meat and served with freshly baked bread. Their fish tacos are also a hit, made with fresh fish, cabbage slaw, and a zesty cilantro lime sauce. Don’t forget to try their Maryland crab soup, a hearty and flavorful soup filled with vegetables and chunks of crab meat.

Live Music:

Enjoy live music every Thursday-Sunday at Dock Street Bar & Grill, featuring local bands playing a variety of genres. The outdoor patio is the perfect spot to relax and enjoy the music while sipping on a cold beer or a refreshing cocktail.

Late-Night Eats:

Craving a late-night snack? Dock Street Bar & Grill has got you covered with their menu available until 1 AM. Whether it’s after a night out or a long day of exploring Annapolis, this restaurant is the perfect spot to satisfy your hunger at any time.

Level a Small Plates Lounge:

Level a Small Plates Lounge in annapolis, MD
Level a Small Plates Lounge in annapolis, MD

Address: 69 West St, Annapolis, MD 21401

Phone: (410) 268-0003

Operating Hours: Tuesday-Saturday: 5 PM – 2 AM; Sunday-Monday: Closed

Reviews: 4.3/5 on Yelp, 4.7/5 on Google, 4.5/5 on TripAdvisor

Must-Try Meals: Duck Fat Fries, Korean Beef Tacos, Crab Tots

Average Cost: $15-$25 per person

Website: https://www.levelannapolis.com/

Menu: http://www.levelannapolis.com/menu.html

A Modern Lounge and Tapas Bar:

Located on West Street, Level a Small Plates Lounge offers a unique dining experience with its tapas-style menu and craft cocktails. The interior is trendy and modern, with dim lighting and a vibrant atmosphere. This is the perfect spot for a fun night out with friends or a romantic date.

Creative Small Plates:

Level a Small Plates Lounge offers a variety of small plates, perfect for sharing and trying new flavors. Their duck fat fries are a must-try, served with truffle aioli and Parmesan cheese. Other popular dishes include their Korean beef tacos, made with marinated short ribs and topped with a spicy slaw, and their crab tots, a twist on the classic tater tots with a creamy crab dip filling.

Craft Cocktails:

The bar at Level a Small Plates Lounge is known for its creative and delicious craft cocktails. From classic favorites to unique creations, there is something for everyone. Try the “Annapolis Mule,” made with local vodka, ginger beer, and lime, or the “Grapefruit Basil Martini” for a refreshing and flavorful drink.

Private Events:

If you are looking to host a private event, Level a Small Plates Lounge offers a private room that can accommodate up to 50 guests. The room features its own bar and customizable menus to fit your event needs.

Davis’ Pub:

Davis' Pub in annapolis, MD
Davis’ Pub in annapolis, MD

Address: 400 Chester Ave, Annapolis, MD 21403

Phone: (410) 268-7432

Operating Hours: Monday-Sunday: 11 AM – 2 AM

Reviews: 4/5 on Yelp, 4.4/5 on Google, 4.5/5 on TripAdvisor

Must-Try Meals: Fish and Chips, Maryland Crab Cakes, Shepherd’s Pie

Average Cost: $15-$25 per person

Website: https://davispub.com/

Menu:https://davispub.com/menu.html

A Traditional Irish Pub:

Located in the Eastport neighborhood, Davis’ Pub is a cozy and welcoming spot that serves traditional Irish dishes and has a wide selection of beers and spirits. The interior is warm and inviting, with dark wood accents, Irish memorabilia, and a friendly atmosphere.

Classic Irish Fare:

Davis’ Pub offers a variety of classic Irish dishes, such as their fish and chips, made with beer-battered cod and served with house-made tartar sauce. Their Maryland crab cakes are also a must-try, made with jumbo lump crab meat and served with coleslaw and fries. For a taste of home-cooked comfort food, try their shepherd’s pie, made with ground beef and vegetables, topped with mashed potatoes and baked until golden brown.

Large Beer Selection:

With over 50 beers to choose from, including local and imported options, Davis’ Pub has something for everyone. From light lagers to full-bodied stouts, their knowledgeable bartenders can help you find the perfect beer to pair with your meal or enjoy on its own.

Live Music:

Enjoy live music every Friday and Saturday night at Davis’ Pub, featuring local bands playing a mix of Irish and contemporary music. The pub also hosts occasional events, such as trivia nights and karaoke, for a fun and lively experience.

Conclusion:

Annapolis is a city full of delicious dining options, and these 12 restaurants represent some of the best the city has to offer. Whether you’re in the mood for seafood, steak, Italian fare, or small plates, there is something for everyone in this charming and historic city. From award-winning restaurants to casual sports bars, each of these establishments offers a unique dining experience that will leave you satisfied and wanting to come back for more. So next time you’re in Annapolis, be sure to check out one (or all!) of these fantastic restaurants and indulge in the local flavors.