Best Restaurants for Special Occasions in Annapolis

Price

$$
$$$
$$$$

Cuisine

AmericanItalianSteakhouseSeafoodFrenchChinese

Regions

Eastern ShoreGreater Annapolis

Neighborhoods

AnnapolisPasadenaStevensville

Top Rated

CharmingFancyGood for business mealsGood for groupsGood for special occasionsGreat for brunch

Dining Options

All dining options

Delivery only

Takeout only

Seating Options

BarCounterStandardHigh TopOutdoor

Accessibility

Wheelchair access

15 restaurants available nearby

How are Featured results ranked

1. Osteria 177

4.9

Exceptional(3582)

$$$$Price: Expensive

• Italian • Annapolis

Booked 23 times today

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.

A photo of Acqua al 2 - Annapolis restaurant

2. Acqua al 2 - Annapolis

4.7

Exceptional(935)

$$$$Price: Expensive

• Italian • Annapolis

Booked 35 times today

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.

A photo of Luna Blu - Annapolis restaurant

3. Luna Blu - Annapolis

4.7

Exceptional(2496)

$$$$Price: Moderate

• Italian • Annapolis

Booked 18 times today

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!

A photo of Level Small Plates Lounge restaurant

4. Level Small Plates Lounge

4.5

Awesome(2275)

$$$$Price: Moderate

• American • Annapolis

Booked 10 times today

Our menu is a fusion of Chesapeake and International flavors, crafted for sharing and inspired by the vibrant Arts District of Downtown Annapolis’ restaurant scene.By sourcing as many ingredients as possible from local and regional farms, our culinary team is able to create the unique dining experience you are craving. We strive to offer a diverse selection that includes gluten-sensitive and vegan options. Our legendary cocktails are handcrafted with fresh and house-made ingredients. Our mixologists pride themselves on creating memorable cocktails that compliment our cuisine and are sure to please every palette.From corporate events and birthday parties to wedding receptions and the actual ceremony, Level is the perfect venue to host your next celebration.In a world filled with distractions, we believe it’s vital to step back, gather with friends and family, and relish in the joy of sharing delicious local cuisine with unforgettable cocktails.

5. Cafe Normandie

4.5

Awesome(2673)

$$$$Price: Moderate

• French • Annapolis

Booked 6 times today

Consistently voted "Most Romantic" restaurant, Cafe Normandie combines French cuisine with local Maryland specialities. A family business, we have been located in Historic Annapolis for 35 years.

A photo of The Choptank - Annapolis restaurant

6. The Choptank - Annapolis

4.6

Exceptional(1618)

$$$$Price: Expensive

• Seafood • Annapolis

Booked 73 times today

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!

A photo of Chart House Prime - Annapolis restaurant

7. Chart House Prime - Annapolis

4.5

Awesome(7270)

$$$$Price: Expensive

• Seafood • Annapolis

Booked 83 times today

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.

A photo of Blackwall Hitch - Annapolis restaurant

8. Blackwall Hitch - Annapolis

4.5

Awesome(2537)

$$$$Price: Expensive

• American • Annapolis

Booked 29 times today

We can't wait for you to dine with us at Blackwall Hitch Annapolis! A dining experience blending the area’s finest in tastes & talents, Blackwall Hitch is a coastally inspired concept that creates a local connection. Here you’ll find seasonally driven and locally sourced food and spirits, great local music and the area’s friendliest staff and patrons. With each visit as you take in the local flavor, we guarantee you’ll be hooked in no time. Get hooked on the flavor.

A photo of Carpaccio Tuscan Kitchen restaurant

9. Carpaccio Tuscan Kitchen

4.7

Exceptional(2404)

$$$$Price: Moderate

• Italian • Annapolis

Booked 25 times today

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.

A photo of Lewnes' SteakHouse restaurant

10. Lewnes' SteakHouse

4.8

Exceptional(3684)

$$$$Price: Very Expensive

• Steakhouse • Annapolis

Booked 24 times today

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.

See what locals rave about

From verified diners like you

R
Roseann
New York City •2 reviews
4.0
Dined 2 days ago
Excellent food as always, attentive service. It is a bit loud, and our waiter had a booming voice- perhaps to overcome atmosphere and noise. I confess we heard the menu, and his spiel multiple times at each surrounding table
More info
Acqua al 2 - AnnapolisPrice: Expensive• Italian• Annapolis
•
4.7
F
FredVIP
Baltimore / Maryland •7 reviews
5.0
Dined 3 days ago
Great italian food, and friendly service. It's a favorite.
More info
Osteria 177Price: Expensive• Italian• Annapolis
•
4.9
C
Connie
Washington, D.C. Area •3 reviews
5.0
Dined 3 days ago
Service and food outstanding. Ambience was loud and close quarters.
More info
Luna Blu - AnnapolisPrice: Moderate• Italian• Annapolis
•
4.7
D
David
South Wales •1 review
4.0
Dined 7 days ago
The food was very good with a wide selection for all tastes. The server was excellent and her advice turned out to be spot on. Enjoyed the meal and the drinks and would certainly go again
More info
Cafe NormandiePrice: Moderate• French• Annapolis
•
4.5
W
william
Baltimore / Maryland •13 reviews
5.0
Dined on Jun 16, 2025
Had a lovely dinner here before a concert at Ramshead. Excellent cocktails, nice wine and outstanding food. The service was fast, friendly and very attentive. Excellent experience all the way around.
More info
Level Small Plates LoungePrice: Moderate• American• Annapolis
•
4.5

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