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Diners' Choice: Most Booked restaurants in Greater Annapolis

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OpenTable
Updated July 05, 2024

Looking for the most booked restaurants in Greater Annapolis? You’re in the right place. Each month, OpenTable analyzes nearly 500,000 new global diner reviews from the past month. We sort the results by location to help you discover new favorite restaurants. It's a great partnership: you reserve, eat, and review. We listen...and deliver the results for all to benefit. Enjoy!


A photo of The Choptank - Annapolis restaurant
4.6
4.6 (1262)
$31 to $50
Seafood
Annapolis
About the restaurant
Local Chesapeake Seafood and Crabhouse featuring live entertainment, craft cocktails, carefully curated wine list, and the best scenic view of the Chesapeake in the region!
Top review
NancyC
Dined 4 days ago
First time here - everything was excellent - we had rockfish ceviche, ciopino and the best fish and chips ever! We eat outside by the water - definitely going back!
A photo of Cooper's Hawk Winery & Restaurant - Annapolis restaurant
4.4
4.4 (6814)
$30 and under
American
Annapolis
About the restaurant
Experience the perfect fusion of award-winning wines, Napa-style tasting rooms, and modern casual dining at Cooper's Hawk Winery & Restaurants. Enjoy contemporary American cuisine influenced by international flavors from our scratch kitchen. Each dish is expertly paired with our selection of wines for the best food and wine match. Whether you explore the tasting room for a pre- or post-dinner adventure or join the world's largest wine club, we believe in the power of food and wine to create lasting connections. Dining reservations are highly recommended, but walk-in guests are always welcome on a first-come, first-serve basis. Gluten-free and vegetarian dishes are available.
Top review
OpenTable Diner
Dined today
The staff made our anniversary dinner memorable and were meticulous and responsive
A photo of Chart House Prime - Annapolis restaurant
4.5
4.5 (6864)
$31 to $50
Seafood
Annapolis
About the restaurant
Original Hospitality. Creative Culinary. Modern Energy.
Experience the evolution of dining with Chart House Prime - where sophistication meets trendsetting cuisine. Our approachable yet professional service, coupled with the finest ingredients, brings you the best in refined seafood and steakhouse cuisine with a unique fusion of elegance and vibrance, creating a truly remarkable experience.

Top review
Longhorn
Dined 2 days ago
Had a friend visiting Annapolis from San Antonio. Requested a table with a water view. Food was excellent, service was very attentive and personal, and our waterfront view made our friend say that he's going to come back in August with his wife:) Great evening. Thanks to everyone who made it perfect.
A photo of Acqua al 2 - Annapolis restaurant
4.7
4.7 (720)
$31 to $50
Italian
Annapolis
About the restaurant
Located in the heart of Annapolis, Acqua al 2 offers an authentic Tuscan dining experience. Featuring a wide array of vegetarian pasta, hand-carved steaks, and fresh seafood, as well as an extensive Italian wine list, Acqua is perfect for a celebratory dinner, an intimate date night, or a low key get-together with friends.
Top review
AlexKvip
Dined 3 days ago
Last night’s dining experience at Acqua al 2 in Annapolis was nothing short of magical! 🍝 From the moment we walked in, we were greeted with the warmest welcome and impeccable service. The intimate setting inside this beautifully restored old bank building added a unique and romantic touch to the evening. 🏦❤️ We started with their famous homemade pasta, which was incredibly fresh and bursting with flavor. Each bite was a testament to their dedication to authentic Italian cuisine. The pasta was perfectly cooked and paired with exquisite sauces that left us wanting more. 🍷🍴 Pro tip: for a spicy dish order the picci alla fiaccheraia 🤤. Their burrata specials are ALWAYS delicious too. The ambiance was simply enchanting – dim lighting, elegant decor, and a cozy atmosphere that made us feel right at home. Whether you’re planning a special date night or just want to indulge in some fantastic Italian food, Acqua al 2 is the place to be.
A photo of Lewnes' SteakHouse restaurant
4.8
4.8 (3458)
$50 and over
Steakhouse
Annapolis
About the restaurant
The Lewnes family has been in the food business since 1921. Lewnes' Steakhouse opened in 1994, specializing in USDA prime beef and exquisite seafood dishes. With its high back booths, low-lit ambiance and a waitstaff that is dedicated to first class service, Lewnes' is the premier spot for special occasions or private dining. Lewnes' boasts a Wine Spectator "Best of Award of Excellence" award winning wine list with over 450 wine selections to pair with your meal.
Top review
AnnapolisMaryvip
Dined 3 days ago
Always amazing! Thank you.
A photo of Osteria 177 restaurant
4.9
4.9 (3339)
$31 to $50
Italian
Annapolis
About the restaurant


Osteria 177 is the ultimate expression of an Italian tavern where the main attraction is imported delicacies of one-of-a-kind food and wine. Adorned by barreled wine, an Osteria would never lack the sought out local specialties, spices, cheeses, fish or meats. It was here that many people tried to alleviate life's stresses by numbering themselves with good food, good wine, and good company. The owner/chef of the Osteria would take the utmost pride in stocking these praised elements as the basis for mouthwatering meals, a delicious dance-for-all of the five senses. This is the basis for Osteria 177.

Top review
OpenTable Diner
Dined 1 day ago
Unreal food. Have to go. Experience was Excellent across the board
A photo of Pusser's Caribbean Grille - Annapolis restaurant
4.1
4.1 (1414)
$30 and under
Caribbean
Annapolis
About the restaurant
Reservations are for inside only, outside dining is sat on a first come first served basis! Come and experience the sunshine at Pusser's Caribbean Grille on Annapolis Harbor. This unique, waterfront restaurant, bar and retail store offers a "taste of the Caribbean" featuring freshly prepared Caribbean cuisine, along with taste-tempting Annapolitan favorites, at an exclusive dockside location in the heart of downtown Annapolis. At the dockside bar, you will find a colorful selection of tropical rum drinks, including the infamous "Pusser's Painkiller." Our Company Store offers a wide variety of privately branded tropical and nautical apparel along with an interesting selection of accessories, spices, chutneys and drink mixes. Whether you decide to dine on our waterfront dock, in front of our romantic fireplace, or simply want to pull your boat up to our dockside bar, Pusser’s Caribbean Grille offers the perfect location for a truly unique, and always fun, dining and drinking experience.
Top review
JPWFOUR
Dined 6 days ago
Always great visiting Pusser’s and sitting by the water!
A photo of The Melting Pot - Annapolis restaurant
4.5
4.5 (2211)
$31 to $50
Fondue
Annapolis
About the restaurant
Fondue is a fun and interactive dining experience - and for more than three decades, The Melting Pot has defined the niche across the American dining scene. At The Melting Pot, fondue truly becomes a memorable four-course dining experience where patrons can dip into something different - and discover all the ingredients for a unique dining experience including a relaxed atmosphere, private tables, attentive service, fine wines and signature fondue dinners.
Top review
OpenTable Diner
Dined 7 days ago
Everything was delicious, and our server Michelle was AWESOME.
A photo of Carpaccio Tuscan Kitchen restaurant
4.7
4.7 (2247)
$30 and under
Italian
Annapolis
About the restaurant
Comfortable, yet Sophisticated. CARPACCIO offers more than just a menu of authentic Italian specialties. Revel in our uptown ambiance indoors or out while you savor the perfectly portioned and exquisitely flavored pastas, pizzas, meats and seafood dishes.
Experience downtown Annapolis on our fountain view patio and comfortably enjoy observing the passersby. Whether you’re meeting a friend for an appetizer and glass of wine or celebrating a family or corporate event, Carpaccio Tuscan Kitchen & Wine Bar combines flavour, service, authenticity, ambiance & style to bring you all the best that Italy has to offer.

Top review
SeaCrisvip
Dined 3 days ago
The food was outstanding. Great service and wine choices. The musical entertainment made the experience complete.
Discover more
A photo of Ruth's Chris Steak House - Annapolis restaurant
4.7
4.7 (2787)
$31 to $50
Steakhouse
Annapolis
About the restaurant
Expect nothing less than an extraordinary meal and first-class service from one of the most outstanding prime steak houses in the world: Ruth's Chris Steak House. Among the most distinctive dining destinations in the area. At Ruth's Chris Steak House your service will always be first class-attentive but never fussy.
Top review
MykSkee
Dined 1 day ago
Another great experience at Ruth Chris Annapolis!! Always a great time driving from outta state as our family enjoys the historic Annapolis area. Hopefully, my wife and I can afford to retire there😊 Our service here was 5 star again. Our greeters were pleasant and valet attendant help us out as parking was limited. Food was delicious and temperature of food was spot on. We tried their T-Bone for 2 as we are ribeye folk. This cut did not disappoint. Especially with the assistance our waiter. We treat ourselves to this restaurant once or twice a year, and this is out favorite location. Thank you Ruth Chris for another great Birthday dinner❤️
Explore Diners' Choice best of Greater Annapolis
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