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day 1
December 3
Morning. Start your day at City Dock, the heart of Annapolis. Take a walk around the dock, and enjoy the stunning view of boats and yachts docked. You can also book a boat tour to enjoy the view from the water.
Afternoon. Head over to the US Naval Academy, the pride of Annapolis, and take a guided tour of the academy. Visit the Naval Academy Museum to learn about the history of the academy and the US Navy.
Evening. Grab a bite at The Federal House Bar & Grille, a restaurant that has been in operation since 1830. The restaurant offers American cuisine, a variety of cocktails, and live music on weekends.
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day 2
December 4
Morning. Take a walk around the historic district of Annapolis, which is lined with beautiful colonial-style buildings. Visit the Maryland State House, which played a crucial role in the formation of the United States.
Afternoon. Visit the William Paca House and Garden, a National Historic Landmark located in the heart of Annapolis. The house was built in the 18th century and is a perfect example of Georgian architecture.
Evening. For dinner, try the Iron Rooster, a restaurant that serves classic American comfort food. The restaurant is known for its chicken and waffles and homemade pop tarts.
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day 3
December 5
Morning. Start your day by exploring the Annapolis Maritime Museum, which showcases the maritime history of Annapolis and the Chesapeake Bay.
Afternoon. Take a scenic drive to the Sandy Point State Park, which offers stunning views of the Chesapeake Bay Bridge. You can also go swimming, fishing, or hiking at the park.
Evening. For dinner, check out Osteria 177, an Italian restaurant that offers a fine dining experience.
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day 4
December 6
Morning. Visit the Banneker-Douglass Museum, a historical museum that highlights the African American experience in Maryland.
Afternoon. Take a walk around the Quiet Waters Park, a 340-acre park that offers beautiful views of the South River. You can also go kayaking, paddleboarding, or biking at the park.
Evening. For dinner, try the Boatyard Bar & Grill, a seafood restaurant that offers a variety of seafood dishes and a great selection of beer.
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day 5
December 7
Morning. Spend the day at the Chesapeake Bay, which is just a short drive from Annapolis. You can go on a boat tour, fishing, or swimming at the bay.
Afternoon. Head back to Annapolis and visit the Annapolis Arts District, which is home to a variety of art galleries and studios.
Evening. End your day at Vin 909 Winecafe, a wine bar that offers delicious food and a great selection of wines.
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