Diners' Choice: Best Overall restaurants in Greater Annapolis

OpenTable

Updated June 05, 2025

Looking for the best overall restaurants in Greater Annapolis? You’re in the right place. Each month, OpenTable analyzes nearly 2 million global diner reviews from the past four months. We sort the results by location and category 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!

Osteria 177

4.9

4.9 (3586)

$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 2 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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4.8

4.8 (3690)

$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 2 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 (327)

$30 and under

Gastro Pub

Annapolis

About the restaurant

An american craft Gastropub concentrating on local and small batch beers, whiskey, spirits and hand crafted cocktails along with a brick oven menu with Wood Fired Pizza, shareable items, and small plates.

*Please note for online wait listed reservations do have a 5-10 min time frame to arrive for your reservation to be sat*

Top review

EmilyVIP

Dined on Jun 14, 2025

Very good! Drinks were so reasonable and pizza was tasty.

Luna Blu - Annapolis

4.7

4.7 (2497)

$30 and under

Italian

Annapolis

About the restaurant

We opened in 2001 on the new up & coming hot spot of Inner West Street. We have grown into a neighborhood favorite among locals & tourists. Our cozy dining room with murals of the Amafi Coast is the perfect place for a date night or for making memories with friends & family. Offering innovative Italian fare prepared with a personal touch & the freshest local ingredients. All menu items are prepared fresh to order, this allows us to be very accommodating to food allergies. We have many options for vegans, pescatarians and gluten free diners.

Wednesday & Saturday from May - Sept on West Street's 1st block we hold Dinner Under the Stars. All of the restaurants put tables & chairs under a light canopy, there is live music and dancing.

We offer a 4 course special nightly, 1/2 priced bottle of we every Wednesday, Pizza & Wine pairing Tuesday & Thursday nights & bi weelky wine dinners.

View our events & specials www.lunabluofannapolis.com

Thanks for supporting local business!

Top review

PatrickVIP

Dined 7 days ago

Great find in a great town. As a local we have been frequenting this establishment over the years, and it just keeps getting better. Great food, great wine selections, great service, great value. This place is authentic Italian with a New York type feel.

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Popular dish

Tiramisu

O'Learys Seafood Restaurant

4.8

4.8 (1942)

$50 and over

Seafood

Edgewater

About the restaurant

O’Learys Seafood Restaurant is arguably the best fresh-fish seafood restaurant in the region, and without a doubt the best seafood restaurant in Annapolis. Located off of Spa Creek facing Historic Annapolis and the U.S. Naval Academy, in the historic Eastport section of Annapolis, O’Learys is an intimate haunt that offers seafood cuisine that is strictly nouveau/fresh, along with “the best small wine list in Annapolis”!

Top review

James

Dined on Jun 22, 2025

Fantastic food, comfortable, quiet setting and great service made for a beautiful evening.

Amore Robiolina

4.8

4.8 (132)

$31 to $50

Italian

Edgewater

About the restaurant

Welcome to Robiolina Amore, a culinary gem nestled in the heart of Edgewater, Maryland. Founded by the visionary Chef Canales, our restaurant is a testament to the passion and dedication of one man's love for authentic Italian cuisine. Here at Robiolina Amore, we take immense pride in our commitment to crafting homemade Italian dishes, ensuring that each bite is a delectable reflection of Italy's rich culinary heritage. Our pasta is lovingly handcrafted in-house, and our menu boasts extravagant Italian creations that will transport your taste buds to the heart of Italy. We offer not just a meal but an experience, with every dish served in a warm and welcoming atmosphere by a team that genuinely cares about your dining pleasure. Join us at Robiolina Amore, where Chef Canales' culinary artistry comes alive with every exquisite bite. Buon appetito!

Top review

CarolVIP

Dined on Jun 5, 2025

Love the food which is consistently wonderful. The service is outstanding. The noise level was very loud Don’t remember that before

Carpaccio Tuscan Kitchen

4.7

4.7 (2408)

$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.

Ruth's Chris Steak House - Annapolis

4.7

4.7 (2921)

$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

Trudy

Dined 6 days ago

We had a wonderful experience celebrating our anniversary, marking 31 for my husband and me, 34 years for our friends.

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Harold Black - Annapolis

4.8

4.8 (75)

$30 and under

Italian

Annapolis

About the restaurant

Given that Harlod Black is a cocktail bar, the age requirement for entering is 21.

Harold Black is a warm, intimate bar that is quiet enough to hear your conversation yet lively enough to keep you talking. A list of house cocktails gives you a range of options; additionally, the bartenders are ready to work their magic if you have something else in mind. Harold Black serves the same menu as Acqua with a couple of pub-style additions. Please be aware of a few house rules: 1. We look forward to having you join us and are happy to hold your table for up to fifteen minutes. 2. Your booking reserves your seats for 2 hours. 3. Due to our small size we cannot guarantee booth seating. 4. Our maximum party size is six people, no exceptions, and unfortunately we cannot book multiple tables for one group. To buy out Harold Black for a private event or book our private dining room, please email events@haroldblack.com.

Top review

Nikol

Dined on Jun 13, 2025

Such a cute spot, completely hidden so it took us a minute to figure out where to go but that just added to the whole experience. We thoroughly enjoyed the drinks, service was amazing, food was great too but we only had appetizers. Highly recommend this spot.

Acqua al 2 - Annapolis

4.7

4.7 (938)

$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 4 days ago

Delicious food, fun cocktails, and great service!

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