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Roam Around

Annapolis: Sailing, Seafood, and History in 3 Days Itinerary

Last updated: 2024 Jun 14

Historic Annapolis and Seafood Delights

Morning

Start your day with a delightful breakfast at Iron Rooster, known for its delicious homemade pop tarts. Afterward, immerse yourself in Annapolis' history with the "Best of Annapolis Tour" Best of Annapolis Tour. Explore the city's iconic landmarks and learn about its rich maritime heritage.

Afternoon

For lunch, savor the fresh seafood at The Point Crab House & Grill while enjoying waterfront views. Afterward, take a leisurely stroll through the historic streets on the "Annapolis Walking In App Audio Tour" Annapolis Walking In App Audio Tour in Sailing Capital. Visit the Naval Academy and the Maryland State House.

Evening

In the evening, enjoy a memorable dining experience at Carrol's Creek Cafe, known for its seafood and waterfront dining. After dinner, take a relaxing sunset cruise on the Chesapeake Bay to end your day.

Bedtime

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Best of Annapolis Tour
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Annapolis Walking In App Audio Tour in Sailing Capital
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Sailing and Scenic Views

Morning

Indulge in a delicious breakfast at Miss Shirley's Cafe, Annapolis, famous for its Southern cuisine. Then, embark on a sailing adventure with the "Best of Annapolis Walking Tour" Best of Annapolis Walking Tour. Experience the thrill of sailing in the "Sailing Capital of the World."

Afternoon

For lunch, head to Boatyard Bar & Grill and enjoy a meal in a nautical setting. Afterward, continue your maritime exploration with a visit to the Annapolis Maritime Museum or take a water taxi to explore the area from the bay.

Evening

Enjoy a relaxed dinner at O'Learys Seafood Restaurant, known for its crab cakes. Afterward, take a leisurely walk along the City Dock and enjoy the evening ambiance of downtown Annapolis.

Bedtime

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Best of Annapolis Walking Tour
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Ghost Tour and Farewell to Annapolis

Morning

For your last morning in Annapolis, have a delightful breakfast at Metropolitan Kitchen & Lounge, known for its creative dishes. Then, experience a different side of the city with the "Phantoms of Annapolis Ghost Walking Tour" Phantoms of Annapolis Ghost Walking Tour. Explore the haunted history of Annapolis.

Afternoon

Enjoy a final seafood feast at Chart House with stunning views of the waterfront. After lunch, take a relaxing walk through the historic district and do some last-minute shopping for souvenirs.

Evening

Conclude your Annapolis adventure with a memorable dinner at Lewnes' Steakhouse, a local favorite. Raise a toast to your time in the city at Galway Bay Irish Pub, known for its cozy atmosphere and wide selection of drinks.

Bedtime

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