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Best Restaurants for Outdoor Dining in Annapolis

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10 restaurants available nearby

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 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 Rams Head Tavern - Annapolis restaurant
4.3
Awesome(1695)
Price: Moderate
• American • Annapolis
Booked 9 times today
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.
A photo of Iron Rooster restaurant
4.4
Awesome(1012)
Price: Moderate
• Breakfast • Annapolis
Booked 13 times today
Whether you're looking for breakfast all day, lunch, supper or drinks, at Iron Rooster you'll find a new twist on traditional comfort food, legendary hospitality, and a real sense of community. Join us every day for breakfast, lunch, supper and late-night drinks. Whenever you're here, you'll enjoy delicious food, a cold drink, and an extra helping of hospitality.
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.
A photo of Cooper's Hawk Winery & Restaurant - Annapolis, MD restaurant
4.5
Awesome(7206)
Price: Moderate
• American • Annapolis
Booked 105 times today
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.
A photo of Urbano - Annapolis restaurant
3.6
Very Good(31)
Price: Moderate
• Mexican • Annapolis
Booked 4 times today
Are you ready to embark on a flavor -packed journey through the heart of Mexico, right here in Annapolis Town Center? Urbano Tex Mex invites you to experience the vibrant colors, bold spices, and authentic tastes of Tex- Mex cuisine like never before.​At Urbano Tex Mex, we are passionate about bringing together the best of Texan and Mexican culinary traditions. Our chefs blend premium ingredients with time-honored recipes to create mouthwatering dishes that will tantalize your taste buds.
A photo of Julep Southern Kitchen & Bar restaurant
4.5
Awesome(118)
Price: Moderate
• American • Annapolis
Booked 1 time today
Your spot for creative southern comfort food, house-made desserts, local craft beer, whiskey, and cocktails, located in Annapolis
A photo of Knoxie's Table at The Inn at the Chesapeake Bay Beach Club restaurant
4.7
Exceptional(1656)
Price: Expensive
• American • Stevensville
Booked 17 times today
Rated the number one restaurant in Stevensville, Knoxie’s Table welcomes guests into a warm rustic setting located off the lobby of The Inn at the Chesapeake Bay Beach Club. Knoxie’s Table offers an authentic dining experience for locals and guests with a menu featuring fresh local seafood and seasonal dishes composed of the area’s finest ingredients. The bar features one of the best whiskey selections in the area along with an extensive selection of wine, beer, and hand-crafted cocktails. Offering both indoor and outdoor dining, Knoxie’s Table features 150 seats with booth and table-style seating, indoor and outdoor fireplaces, indoor bar seating, and an outdoor bar and terrace overlooking The Inn’s expansive gardens, fire pits, and fountains.
A photo of 18Twenty restaurant
4.7
Exceptional(191)
Price: Expensive
• Contemporary American • Stevensville
Booked 3 times today
For an exclusive Valentine's Day private chef experience, please call or email the resort directly. dalmeida@kentislandresort.com https://www.kentislandresort.com/valentines-menu/

See what locals rave about

From verified diners like you
From verified diners like you
  • Linda
    Washington, D.C. Area •2 reviews
    5.0
    Dined 2 days ago
    We had a wonderful experience at Carpaccio’s thanks to our server, Meg. She was wonderful!! The food was absolutely delicious too. We’re looking forward to going back.
    More info
    Carpaccio Tuscan KitchenPrice: Moderate• Italian• Annapolis
    4.6
  • 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
  • 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
  • Chip
    Jackson Hole / Wyoming •1 review
    5.0
    Dined on Feb 8, 2025
    We had dinner at Rams Head prior to a show we were attending as part of their Premium On Stage Experience which we now take advantage of every time we see a show there. The place was packed but the noise was manageable and our server John(Jon) was friendly, attentive and we were not rushed but made it to our seats 15 minutes before the start of the show. We were also seated next the fireplace which was a plus as it was cold and wet outside. Our meals were very good and as always the Copperhead Ale was excellent. My only criticism has to do with the cost of my meal. I ordered one of the dinner specials, the Drunkn Noodles and the dish was very good and had plenty of shrimp but it was also supposed to have lump crab meat. There was very little crab meat (no lump that I could find) and for the $26 cost I felt there should have been a lot more crab meat. All that said still and wonderful meal and show!
    More info
    Rams Head Tavern - AnnapolisPrice: Moderate• American• Annapolis
    4.3
  • Eleanor
    Washington, D.C. Area •2 reviews
    5.0
    Dined on Dec 24, 2024
    Rachel took wonderful care of us. The food was delicious and served very promptly. There was a mix up with our Open Table reservation but manager Robert promptly texted me the morning of to accommodate us at an earlier seating because of the holiday. Rachel was very hospitable and made sure we had everything we needed. From the cocktails, to the appetizer, to the entrees and desserts we took to go, an outstanding meal. It was the perfect Christmas Eve dinner for our little family. A well-deserved reputation as an excellent establishment.
    More info
    Iron RoosterPrice: Moderate• Breakfast• Annapolis
    4.4
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