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4 Days of Charm in Annapolis and Baltimore

4 Days of Charm in Annapolis and Baltimore Itinerary

Last updated: 2024 Jun 22

Historic Beginnings and Waterfront Wonders

Morning
Start your day with a visit to the Maryland State House, the oldest state capitol still in continuous legislative use. This historic building offers a glimpse into the rich history of Annapolis and its role in American history. Afterward, take a leisurely stroll through the picturesque streets of downtown Annapolis, admiring the colonial architecture and charming shops. For breakfast, head to Chick & Ruth's Delly, a local favorite known for its hearty breakfast options and friendly atmosphere. Enjoy classic American breakfast dishes while soaking in the local vibe.
Afternoon
In the afternoon, embark on Best of Annapolis Walking Tour. This tour will take you through some of the most iconic landmarks in Annapolis, including St. Anne's Church, City Dock, and the United States Naval Academy. Learn about the city's fascinating history and enjoy beautiful waterfront views along the way. For lunch, stop by Carrol's Creek Cafe, located right on the waterfront. Savor delicious seafood dishes while enjoying stunning views of Spa Creek.
Evening
As evening approaches, explore City Dock further to experience its vibrant atmosphere. Watch boats come and go while enjoying a relaxing walk along Ego Alley. For dinner, dine at O'Learys Seafood Restaurant, renowned for its fresh seafood and elegant setting. End your night with a drink at McGarvey's Saloon & Oyster Bar, where you can enjoy local craft beers and oysters.
Bedtime
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Naval Heritage and Ghostly Tales

Morning
Begin your second day with a visit to the United States Naval Academy. Take a guided tour to learn about this prestigious institution's history and traditions. Don't miss Bancroft Hall and the Naval Academy Chapel. For breakfast, try Iron Rooster, famous for its homemade pop-tarts and all-day breakfast menu.
Afternoon
After exploring the Naval Academy, head over to Quiet Waters Park for some outdoor relaxation. Rent a kayak or paddleboard to explore South River or simply enjoy a peaceful walk through the park's scenic trails. Lunch at Grumps Cafe is highly recommended for its casual dining atmosphere and delicious burgers.
Evening
In the evening, join Phantoms of Annapolis Ghost Walking Tour. Discover spooky tales of haunted sites around Annapolis as you walk through historic streets under moonlight. Dinner at Vin 909 Winecafe will be perfect for ending your day with farm-to-table cuisine paired with excellent wines.
Bedtime
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Culinary Delights and Historic Heights in Baltimore

Morning
Begin your day with a visit to the iconic Fort McHenry National Monument and Historic Shrine, the birthplace of the American national anthem. Explore the fort's history and enjoy panoramic views of the harbor.
Afternoon
Evening

Scavenger Hunts and Haunted Pubs

Morning
Start your final day with a visit to William Paca House & Garden, an 18th-century Georgian mansion that offers insights into colonial life in Annapolis. Explore beautifully restored rooms and stroll through lush gardens. Breakfast at Eggcellence Brunchery is ideal for enjoying gourmet brunch dishes in a cozy setting.
Afternoon
Engage in some fun with Annapolis: Private Scavenger Hunts. This interactive activity will have you solving clues around town while discovering hidden gems along the way. For lunch, head over to Miss Shirley's Cafe where you can indulge in Southern-inspired comfort food.
Evening
Conclude your trip with an exciting evening on Annapolis: Crabtown Boos and Booze Haunted Pub Crawl. Visit several haunted pubs around town while hearing chilling ghost stories from your guide. Finish off with dinner at Level Small Plates Lounge, known for its creative small plates menu that offers something for everyone.
Bedtime
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Annapolis: Private Scavenger Hunts

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Visit Annapolis Crabtown Boos and Booze Haunted Pub Crawl in Annapolis

Annapolis: Crabtown Boos and Booze Haunted Pub Crawl

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