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5 Days of Charm in Baltimore, Annapolis, and DC

5 Days of Charm in Baltimore, Annapolis, and DC Itinerary

Last updated: 2024 Jun 14

Exploring Baltimore's Historic Heart

Morning
Start your day with a visit to Fort McHenry National Monument and Historic Shrine. This historic site is where the Star-Spangled Banner was written during the War of 1812. The fort offers a rich history and beautiful views of the harbor. After exploring the fort, head to Blue Moon Cafe for a hearty breakfast known for its famous Captain Crunch French Toast.
Afternoon
In the afternoon, take a stroll through Fell’s Point, one of Baltimore's oldest neighborhoods. Enjoy its cobblestone streets, historic buildings, and waterfront views. Don't miss out on Baltimore Fells Point Walking Foodie and History Tour to taste local delicacies while learning about the area's history. For lunch, stop by Thames Street Oyster House for some fresh seafood.
Evening
As evening approaches, make your way to Baltimore Inner Harbor. This bustling area is perfect for an evening walk with plenty of shops and attractions. Embark on Baltimore Inner Harbor Moonlight Cruise on a Classic Ship to see the city lights from the water. End your day with dinner at Rusty Scupper Restaurant & Bar, offering stunning views of the harbor.
Bedtime
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Cultural Gems and Scenic Views in Baltimore

Morning
Begin your second day at the fascinating American Visionary Art Museum, which showcases unique and thought-provoking artworks by self-taught artists. Follow this cultural experience with breakfast at Papermoon Diner, known for its eclectic decor and delicious morning fare.
Afternoon
Next, head over to explore Baltimore National Aquarium, one of the top aquariums in the country featuring thousands of marine creatures. Afterward, enjoy lunch at Miss Shirley’s Cafe, famous for its Southern-inspired dishes. Post-lunch, visit Maryland Science Center where interactive exhibits will captivate visitors of all ages.
Evening
In the evening, take part in an exciting activity: join The Original Fells Point Haunted Pub Walk. This tour combines ghost stories with visits to historic pubs in Fell’s Point. Conclude your night with dinner at Black Olive, offering Mediterranean cuisine in a cozy setting.
Bedtime
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Historic Highlights and Scenic Sails in Annapolis

Morning
Drive from Baltimore to Annapolis (approximately 45 minutes). Start your Annapolis adventure with a visit to the U.S. Naval Academy where you can explore its rich history and beautiful campus (guided tours available). Have breakfast at Chick & Ruth’s Delly, known for its hearty meals and quirky atmosphere.
Afternoon
Spend your afternoon wandering around downtown Annapolis' charming streets lined with colonial buildings. Join the informative Best of Annapolis Walking Tour to get an insider's view of this historic city. For lunch, dine at Carrol’s Creek Cafe which offers waterfront dining with delicious seafood options.
Evening
In the evening, experience something unique by renting an electric boat through Annapolis: Electric Boat Rental - Duffy Sun Cruiser - 10ppl. Enjoy cruising along Chesapeake Bay as you watch the sunset over serene waters. Wrap up your day with dinner at O’Learys Seafood Restaurant, renowned for its fresh seafood dishes.
Bedtime
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Monuments and Memorials in DC

Morning
Start your day in Washington, DC with a visit to the iconic Lincoln Memorial. This monumental tribute to Abraham Lincoln is a must-see and offers stunning views of the Reflecting Pool and Washington Monument. Afterward, enjoy breakfast at Founding Farmers, known for its farm-to-table dishes and hearty breakfasts.
Afternoon
In the afternoon, explore the vast National Mall, home to numerous significant landmarks. Visit the National Museum of African American History and Culture to delve into important aspects of American history. For lunch, head to Old Ebbitt Grill, a historic restaurant serving classic American fare.
Evening
As evening falls, take part in Washington DC National Mall Night Tour. This guided tour will allow you to see the beautifully illuminated monuments and memorials. End your day with dinner at Martin’s Tavern, a historic eatery in Georgetown known for its cozy atmosphere and delicious meals.
Bedtime
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Historic Sites and Cultural Experiences in DC

Morning
The Smithsonian is an excellent way to start your final day in DC. Choose from one of its many museums such as the National Air and Space Museum or the National Museum of Natural History. Enjoy breakfast at Ted’s Bulletin, famous for its homemade pop-tarts and classic diner fare.
Afternoon
Georgetown awaits you in the afternoon with its charming streets, historic homes, and vibrant shopping scene. Join Washington D.C. Taste of Georgetown Walking Food Tour for a culinary adventure through this picturesque neighborhood. For lunch, stop by Farmers Fishers Bakers located on the waterfront.
Evening
Private DC at Night Tour is perfect for your last evening in Washington, DC. This private tour will take you around the city’s most famous landmarks beautifully lit up after dark. Conclude your trip with dinner at The Hamilton, offering a diverse menu and live music performances.
Bedtime
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