Alyssa & Roy
Things To Do
Chick & Ruth's Delly
Chick and Ruth's Deli is a beloved Annapolis spot known for its hearty sandwiches and classic diner atmosphere. Famous for its breakfast served all day, you can indulge in everything from their signature crab cakes to their towering deli sandwiches. The nostalgic decor and friendly staff make it a perfect place to grab a bite with family and friends while soaking in the local charm. Don’t miss the daily Pledge of Allegiance at 8:30 AM every morning—a unique tradition that adds a special touch to your visit.
Banneker-Douglass-Tubman Museum
The Banneker-Douglass Museum, located in downtown Annapolis, is Maryland’s official museum of African American heritage. This museum offers engaging exhibits and programs that celebrate and preserve the contributions of African Americans in Maryland’s history. From historical artifacts to contemporary art, the museum provides a rich and educational experience for visitors of all ages. It’s a great place to explore and learn more about the state’s diverse cultural heritage.
GameOn bar+arcade Annapolis
Get ready for some fun at Game On Bar + Arcade! This lively venue combines a full-service bar with a fantastic selection of arcade games and classic pinball machines. Whether you're in the mood for delicious pub fare, craft cocktails, or friendly competition, Game On has it all. It's an ideal spot to unwind, enjoy some laughs, and create lasting memories with friends and fellow guests.
Annapolis City Dock
Check out the bustling Annapolis City Dock! This picturesque waterfront area is the heart of the city, offering a mix of history, charm, and fun activities. Enjoy a leisurely walk along the dock with stunning harbor views, watching sailboats and yachts glide by. Explore unique shops and boutiques, or savor fresh seafood at waterfront restaurants and cafes. Don’t miss the Kunta Kinte-Alex Haley Memorial, a powerful tribute to history and resilience. A highlight is Ego Alley, a narrow waterway where boaters show off their vessels, perfect for people-watching and soaking in maritime culture. The City Dock often features live music, festivals, and events that bring the community together. Whether you’re looking to relax by the water, enjoy local cuisine, or explore charming streets, Annapolis City Dock has something for everyone. Come soak up the vibrant atmosphere and make the most of your Annapolis adventure!
Miss Shirley's Cafe
Miss Shirley's Cafe offers a delightful dining experience that’s perfect for brunch or lunch. Known for its creative twists on classic comfort food, you can savor dishes like their famous French toast, shrimp and grits, or a hearty breakfast bowl. The warm and inviting atmosphere, along with friendly service, makes it a great place to gather with loved ones and enjoy a delicious meal before exploring more of Annapolis.
Hammond-Harwood House
The Hammond-Harwood House is a museum of 18th century architecture and art standing as a testament to the importance of preservation to the residents of Annapolis, and America. Built in 1774, this National Historic Landmark presents a window into the lives of the people who built the house, lived in it, and ensured that it would be enjoyed by future generations for years to come. Tours of the House highlight its refined design, unique history, and incomparable collection of paintings by Charles Willson Peale and furniture by John Shaw. Open daily noon to 5 p.m, closed on Tuesday.
Light House Bistro
Lighthouse Bistro is a charming and unique dining spot in downtown Annapolis, offering delicious meals with a mission. This cozy bistro is known for its farm-to-table cuisine, featuring fresh, locally-sourced ingredients in every dish. From savory breakfast options to delectable dinner entrees, the menu is crafted to delight your taste buds. What makes Lighthouse Bistro truly special is its commitment to social impact. As part of the Light House Homeless Prevention Support Center, the bistro provides job training and employment opportunities to individuals experiencing homelessness. By dining here, you’re not only enjoying a fantastic meal but also supporting a cause that strengthens the community. With its warm ambiance, friendly staff, and mouth-watering dishes, Lighthouse Bistro is a must-visit for a memorable dining experience in Annapolis.
Annapolis Arts District
make sure to explore the vibrant Annapolis Arts District! Located along West Street, this lively area is a haven for art lovers, bursting with colorful murals, eclectic galleries, and unique shops. Take a leisurely stroll through the district and discover local artists showcasing their talents in a variety of mediums, from painting and sculpture to jewelry and pottery. The Annapolis Arts District also hosts various events throughout the year, including art walks, live music, and cultural festivals, so there's always something exciting happening. Whether you're an art enthusiast or just looking for a fun and inspiring way to spend the day, the Annapolis Arts District is the perfect destination for a memorable and creative adventure. Don’t forget to stop by some of the cozy cafes and restaurants in the area to refuel and soak in the artistic atmosphere!
Kilwins Ice Cream - Chocolate - Fudge
Kilwin's an "old fashioned sweet shop" serves the finest chocolates, fudge, and ice cream. Watch fudge being paddled, caramel apples dipped, peanut brittle stretched or just enjoy a treat.
Maryland State House
The Maryland State House is open to the public every day from 9:00 a.m. to 5:00 p.m., except on Christmas and New Year's Day. Dive into the rich history and charm of this iconic building with a self-guided tour—information is available in the Office of Interpretation on the first floor. Want to dive deeper? Specialized curatorial tours of the building and its stunning artwork can be arranged by appointment—just call 410-260-6445. If you prefer a guided experience, several private tour operators also offer fascinating tours of Annapolis and the State House. Heads up on Security: Security measures are in place at the State House and other state buildings in the Annapolis complex. Be sure to bring a photo ID for entrance, and be prepared for metal detectors.
Drummer's Lot Pub
Looking for a cozy spot to unwind in downtown Annapolis? Drummers Lot Pub is the perfect place! Known for its friendly atmosphere and great selection of drinks, this local gem offers a welcoming vibe for both regulars and visitors. Enjoy a pint of your favorite beer or try one of their signature cocktails while you relax and chat with friends. With its charming decor and lively ambiance, Drummers Lot Pub is a great choice for a fun night out in Annapolis. Cheers to good times and great company!
Original Annapolis Ghost Tours & Crawls
Get ready for a spooky adventure with Annapolis Ghost Tours by Tours and Crawls! Discover the haunted history of Annapolis on a guided tour through its eerie streets and historic sites. Listen to chilling tales of ghostly encounters and mysterious happenings as you explore some of the city's most haunted locations. It's a fun and thrilling way to experience Annapolis at night, perfect for those who love a good scare. Don’t miss out on this unique and unforgettable experience!
Visit the United States Naval Academy
If you have some extra time during your visit to Annapolis, we highly recommend exploring the U.S. Naval Academy! Take a stroll through the scenic grounds, visit the stunning Naval Academy Chapel, and stop by the crypt of John Paul Jones, the father of the U.S. Navy. History buffs will love the Naval Academy Museum, which showcases fascinating artifacts and maritime history. You can also check out the gift shop for unique Navy souvenirs. Just remember to bring a valid photo ID for entry, as the Academy is an active military facility.