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Best Date Night Restaurants in Annapolis

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28 restaurants available nearby

A photo of Acqua al 2 - Annapolis restaurant
4.7
Exceptional(863)
Price: Expensive
• Italian • Annapolis
Booked 42 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 Osteria 177 restaurant
4.9
Exceptional(3505)
Price: Expensive
• Italian • Annapolis
Booked 21 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 Luna Blu - Annapolis restaurant
4.8
Exceptional(2450)
Price: Moderate
• Italian • Annapolis
Booked 13 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 Harold Black - Annapolis restaurant
4.5
Awesome(71)
Price: Moderate
• Italian • Annapolis
Booked 4 times today
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 a light-fare menu with a selection of cured meats, cheeses and desserts. 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. 5. Given that Harlod Black is a cocktail bar, the age requirement for entering is 21. To buy out Harold Black for a private event or book our private dining room, please email events@haroldblack.com.
A photo of Cafe Normandie restaurant
4.4
Awesome(2609)
Price: Moderate
• French • Annapolis
Booked 21 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 Level Small Plates Lounge restaurant
4.5
Awesome(2248)
Price: Moderate
• American • Annapolis
Booked 10 times today
Level was established as a locals first atmosphere with welcoming attitudes to all. Our cocktails are all handcrafted with fresh juices, mixes, and garnishes. One of the many things that makes us unique is our ability and commitment to source as many fresh ingredients locally from the State of Maryland and surrounding markets. We are dedicated to supporting the area small businesses, watermen, farmers, and the environment on a local and global level. Our small plates style of dining encourages this sense of community and sharing. Level is located on the second block of West Street known as the Arts District.
A photo of Red Red Wine Bar restaurant
4.6
Exceptional(89)
Price: Expensive
• Contemporary American • Annapolis
Booked 2 times today
Casual contemporary American made-from-scratch cuisine focused on seasonal entrées, house-made pizzas, cheese and charcuterie boards. Extensive wines by the glass program with something for everyone including local, craft beer and seasonal craft cocktails. A cozy, Bohemian haunt where you and your crew can get away from it all or enjoy one of the biggest outdoor dining patios in downtown Annapolis.
A photo of Chart House Prime - Annapolis restaurant
4.5
Awesome(7136)
Price: Expensive
• Seafood • Annapolis
Booked 61 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 Lewnes' SteakHouse restaurant
4.9
Exceptional(3603)
Price: Very Expensive
• Steakhouse • Annapolis
Booked 29 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.
A photo of Carpaccio Tuscan Kitchen restaurant
4.6
Exceptional(2345)
Price: Moderate
• Italian • Annapolis
Booked 18 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.

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See what locals rave about

From verified diners like you
From verified diners like you
  • Jack
    Philadelphia County •6 reviews
    5.0
    Dined 3 days ago
    Dined for Valentine’s Day set menu. AMAZING!!! Did not feel like a typical Valentine’s Day restaurant production line - in and out ASAP to turn the tables over. Food was incredible. Plenty of time to enjoy the whole experience. Our server Alice was amazing.
    More info
    Acqua al 2 - AnnapolisPrice: Expensive• Italian• Annapolis
    4.7
  • Ethan
    Baltimore / Maryland •3 reviews
    5.0
    Dined 3 days ago
    Service and food was top notch. They made a few minor adjustments to make a few dishes kid friendly. I sincerely appreciated that. If I had to put a negative it would’ve just been the cold gusts of air every time the door opened.
    More info
    Level Small Plates LoungePrice: Moderate• American• Annapolis
    4.5
  • Edward
    Baltimore / Maryland •1 review
    5.0
    Dined 3 days ago
    We were their for lunch. The food was excellent and abundant. The hostess and waitress were welcoming and very efficient. Prices were very fair. Next time we go for dinner
    More info
    Luna Blu - AnnapolisPrice: Moderate• Italian• Annapolis
    4.8
  • Scott
    Minneapolis - St. Paul •1 review
    5.0
    Dined 4 days ago
    This was our first experience at Osteria, but it will definitely not be our last. The food was amazing. The service was top-notch. All of the staff were professional and super friendly. The old fashioned I had was one of best I've ever had. Without a doubt, this was THE best dining experience my wife and I have had in Annapolis.
    More info
    Osteria 177Price: Expensive• Italian• Annapolis
    4.9
  • ElaineVIP
    Washington, D.C. Area •19 reviews
    5.0
    Dined 4 days ago
    Wow! What a great place. I contacted Red, Red Wine when planning a Galentine's Day Happy Hour gathering for our retired womens' group. Lisa replied by email and was very accommodating. When I arrived a bit early, they helped me to set up. Sara was the bartender/server this afternoon, and she did an amazing job of keeping eight different orders straight. Their happy hour drink and food specials are delicious and very reasonable. The daily wine specials were a great value for $5. The individual size crab dip was really yummy, as were the brussel sprouts. I have been planning happy hour events for a year for our group, and this place definitely gets my vote for best Happy Hour around Annapolis.
    More info
    Red Red Wine BarPrice: Expensive• Contemporary American• Annapolis
    4.6

Discover best date night restaurants in Annapolis

For a memorable date night in the picturesque settings of Baltimore, Annapolis or Greater Annapolis, our selection of restaurants offers a variety of romantic dining experiences. Each establishment is carefully chosen to enhance your special evening with a blend of ambiance, gourmet cuisine, and exceptional service. From intimate bistros to elegant eateries, the dining scene in these locations is vibrant and diverse, catering to different tastes and preferences. The atmosphere in these restaurants typically combines a cozy, inviting vibe with sophisticated decor, making them perfect for a night out with your significant other. Patrons can expect to enjoy a range of culinary delights, from fresh seafood caught in the Chesapeake Bay to expertly prepared international dishes. These restaurants not only promise a delightful meal but also a truly enchanting experience that makes any date night special. Discover the ideal spot for romance and fine dining in the heart of Maryland, where every meal is an occasion to remember.

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