Diners' Choice: Most Booked restaurants in Greater Annapolis

OpenTable

Updated June 05, 2025

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!

Cooper's Hawk Winery & Restaurant - Annapolis, MD

4.4

4.4 (7388)

$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

Asher

Dined 4 days ago

From the arrival and entire time the attention from Maddie , Matt and the entire team 5 Stars.

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Popular dish

Shrimp and Scallop Risotto

Popular dish

Blackened Ahi Tuna

Popular dish

Crispy Brussels Sprouts

The Choptank - Annapolis

4.6

4.6 (1628)

$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

David

Dined 3 days ago

Very good but expensive. Nice atmosphere and friendly service.

Chart House Prime - Annapolis

4.5

4.5 (7281)

$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

SandraVIP

Dined on Jun 24, 2025

The Chart House salad is something I could eat everyday. I had the Seafood linguini and it was fabulous. Great service and always a great place!!!

Firebirds Wood Fired Grill - Annapolis

4.6

4.6 (108)

$30 and under

American

Annapolis

About the restaurant

Firebirds Wood Fired Grill is your destination for bold flavors and warm hospitality. From expertly crafted wood-fired steaks and fresh seafood to signature cocktails, mocktails, and curated wines, every detail is designed to deliver an unforgettable dining experience. Whether you're gathering with family, hosting a client, or toasting to a special occasion, Firebirds offers elevated cuisine at an approachable price. Join us for Happy Hour at the FIREBAR® or on the patio and let us show you what extraordinary dining feels like. Reserve your table today — we can’t wait to serve you.

Top review

Florie1031@gmail.com

Dined 1 day ago

Repeat customer! Great food and service and very pleasant staff. Music was a little louder than I would prefer.

Acqua al 2 - Annapolis

4.7

4.7 (939)

$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

CathyVIP

Dined 5 days ago

Delicious food, fun cocktails, and great service!

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4.8

4.8 (3691)

$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

Nick

Dined 3 days ago

It was our 34Th wedding anniversary as we shared a quiet relaxing evening with a delicious evening dinner out together.

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4.9

4.9 (3587)

$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

Stacie

Dined 3 days ago

I love this restaurant. The food is incredible and fresh it reminds of my time in Italy. Our waiter was attentive and accurate with our order and provided exceptional service

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Carpaccio Tuscan Kitchen

4.7

4.7 (2410)

$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

Mohamedu

Dined on Jun 25, 2025

Excellent food - wonderful ambience - genuine Italian cuisine.

The Melting Pot - Annapolis

4.7

4.7 (2246)

$31 to $50

Fondue

Annapolis

About the restaurant

Melting Pot in Annapolis is a locally owned, romantic fondue restaurant offering an intimate, unique, and interactive dining experience. Voted 'Most Romantic Restaurant,' we are the go-to destination for couples, celebrations, families, and unforgettable nights out. Enjoy a cozy, private-table setting with attentive service, fine wines, and our signature four-course fondue experience. From rich, creamy cheese fondue to decadent chocolate fondue, every bite is crafted for a truly special evening. Our friendly servers guide you through each course, ensuring a seamless and enjoyable dining experience. Whether it’s date night, an anniversary, or a special occasion, dip into something fun and different, and make lasting memories at Melting Pot.

Top review

MarkVIP

Dined 5 days ago

Another great experience at Annapolis Melting Pot, with stellar service and delicious food.

Rams Head Tavern - Annapolis

4.4

4.4 (1745)

$30 and under

American

Annapolis

About the restaurant

For over 30 years, Rams Head has been an award-winning favorite serving creative tavern fare. Rams Head offers an outstanding happy hour, a legendary beer selection, and extraordinary live music 7 nights a week. Whether in one of the cozy dining rooms, the historic pub, or on the Wisteria-covered patio, you'll see why so many Annapolitans consider Rams Head their second home. .

We do not accept reservations for outdoor dining.

Have tickets to a show at Rams Head On Stage? If taking advantage of our FREE Premium On Stage Experience, please make note in the 'special request' section while making your reservation.

Top review

MelissaVIP

Dined 4 days ago

The ambiance, service and food were all excellent! Serving sizes were generous.

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