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Roam Around

5 Days in Annapolis Maryland Itinerary

Last updated: 2024 Jun 14

Exploring Historic Annapolis

Morning

Start your day with a visit to the historic downtown area of Annapolis. Begin with a hearty breakfast at Iron Rooster, known for its all-day breakfast menu and homemade pop-tarts. Afterward, embark on the Best of Annapolis Walking Tour to get an overview of the city's rich history and beautiful architecture.

Afternoon

For lunch, head to Chick & Ruth's Delly, a local favorite known for its delicious sandwiches and milkshakes. After lunch, continue exploring with the Annapolis Walking In App Audio Tour in Sailing Capital, which will guide you through the city's maritime heritage and landmarks.

Evening

In the evening, enjoy dinner at Osteria 177, an upscale Italian restaurant offering a variety of seafood dishes. After dinner, experience some spooky fun with the Phantoms of Annapolis Ghost Walking Tour, which takes you through haunted sites in the city.

Bedtime

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Best of Annapolis Walking Tour
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Annapolis Walking In App Audio Tour in Sailing Capital
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Maritime Adventures

Morning

Begin your day with breakfast at Miss Shirley's Cafe, famous for its Southern-inspired dishes and award-winning brunch. Then head to the United States Naval Academy for a guided tour to learn about its history and significance.

Afternoon

For lunch, visit Boatyard Bar & Grill for some fresh seafood and classic American fare. Spend your afternoon on a sailing excursion in Chesapeake Bay to experience Annapolis from the water.

Evening

Dine at Vin 909 Winecafe, known for its farm-to-table cuisine and extensive wine list. Conclude your day with a relaxing stroll along City Dock to enjoy views of the harbor.

Bedtime

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Cultural Exploration

Morning

Have breakfast at Preserve Restaurant where you can enjoy modern American cuisine with locally sourced ingredients. Visit the Banneker-Douglass Museum to explore African American history and culture in Maryland.

Afternoon

Lunch at Mason's Famous Lobster Rolls is a must-try for lobster lovers. Afterward, take part in Annapolis Private Scavenger Hunts for an interactive way to discover hidden gems around town.

Evening

Enjoy dinner at Lewnes' Steakhouse offering prime steaks and seafood options. Later in the evening join Annapolis Crabtown Boos and Booze Haunted Pub Crawl combining ghost stories with local pubs.

Bedtime

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Annapolis Private Scavenger Hunts
Book Now

Annapolis Crabtown Boos and Booze Haunted Pub Crawl
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Outdoor Fun and Relaxation

Morning

Start your morning with breakfast at The Federal House Bar & Grille featuring classic American breakfasts. Head over to Quiet Waters Park for some outdoor activities like hiking or kayaking.

Afternoon

Grab lunch from Grump's Cafe before heading back into town where you can visit St. Anne’s Church or explore local shops on Main Street.

Evening

Dine at Carrol's Creek Cafe offering waterfront dining experience with delicious seafood options while enjoying sunset views over Spa Creek.

Bedtime

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Final Day Highlights

Morning

Begin your last day with breakfast at Sofi's Crepes known for their sweet & savory crepes made fresh-to-order followed by visiting William Paca House & Garden showcasing colonial architecture & beautiful gardens.

Afternoon

Have lunch at Galway Bay Irish Restaurant serving traditional Irish dishes then take part in Best of Annapolis Tour covering key highlights across town including historical landmarks & scenic spots.

Evening

End your trip dining at Chart House renowned not only for its seafood but also stunning waterfront views perfect way wrap up memorable trip.

Bedtime

Find amazing hotels in Annapolis, Maryland.