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Best Fun Restaurants in Annapolis

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29 restaurants available nearby

A photo of Fox's Den restaurant
1. Fox's Den
4.7
Exceptional(308)
Price: Moderate
• Gastro Pub • Annapolis
Booked 17 times today
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*
A photo of Level Small Plates Lounge restaurant
2. Level Small Plates Lounge
4.6
Exceptional(2234)
Price: Moderate
• American • Annapolis
Booked 8 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 Acqua al 2 - Annapolis restaurant
3. Acqua al 2 - Annapolis
4.8
Exceptional(838)
Price: Expensive
• Italian • Annapolis
Booked 45 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 Harold Black - Annapolis restaurant
4. Harold Black - Annapolis
4.4
Awesome(67)
Price: Moderate
• Italian • Annapolis
Booked 5 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 Luna Blu - Annapolis restaurant
5. Luna Blu - Annapolis
4.8
Exceptional(2436)
Price: Moderate
• Italian • Annapolis
Booked 15 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
6. Red Red Wine Bar
4.5
Awesome(85)
Price: Expensive
• Contemporary American • Annapolis
Booked 8 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
7. Rams Head Tavern - Annapolis
4.3
Awesome(1690)
Price: Moderate
• American • Annapolis
Booked 4 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 The Choptank - Annapolis restaurant
8. The Choptank - Annapolis
4.6
Exceptional(1467)
Price: Expensive
• Seafood • Annapolis
Booked 43 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
9. Chart House Prime - Annapolis
4.6
Exceptional(7106)
Price: Expensive
• Seafood • Annapolis
Booked 50 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 Seasalt Annapolis restaurant
10. Seasalt Annapolis
4.6
Exceptional(52)
Price: Expensive
• Seafood • Annapolis
Booked 32 times today
SEASALT is an ingredient driven seafood restaurant and raw bar located in the States Capital. We source fresh, seasonal, and sustainable fish, shellfish, meats, and produce. We thoughtfully and creatively make seafood dishes that have amazing global flavors. The SEASALT bar is a comfortable and friendly gathering place that serves award winning cocktails, curated spirits, wines, and beers. We like to say that we deliver all of this with true Irish hospitality and Southern charm.

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Discover best fun restaurants in Annapolis

Discover the vibrant dining scene in Baltimore, Maryland, and Greater Anapolis, where "fun" is the keyword in every gastronomic adventure! This region thrives with a variety of restaurants that promise not just meals but memorable experiences. From interactive dining setups that engage all your senses to lively atmospheres perfect for both lively group outings and cozy, playful dates, each establishment brings its own unique flair to the table. Culinary creativity is at the forefront, with menus featuring everything from gourmet twists on comfort food to innovative dishes that cater to health-conscious diners. The dining scene here is characterized by a blend of casual sophistication and inviting charm, making it a top choice for anyone looking to combine great food with great times. Whether you're a local or a visitor, these restaurants in Baltimore and Greater Annapolis offer the perfect backdrop for enjoying life and delicious cuisines. Expect top-notch service, a warm ambiance, and a dining experience that will make you want to return time and again.

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