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Annapolis: Sailing Capital's Charm and Culinary Delights Itinerary
Last updated: 2024 Jun 14Historic Annapolis and Waterfront Dining
Morning
Start your day with a delightful breakfast at Iron Rooster, known for its delicious comfort food. Afterward, immerse yourself in the maritime history of Annapolis with the Annapolis Walking In App Audio Tour in Sailing Capital. Explore the charming streets at your own pace, learning about the city's nautical heritage.
Afternoon
For lunch, savor the fresh seafood at Carrol's Creek Cafe while enjoying panoramic views of the harbor. Afterward, take a relaxing cruise on the Annapolis Harbor Cruise to see the city from the water. Learn about the naval academy, historic landmarks, and the Chesapeake Bay.
Evening
In the evening, experience a true Annapolis institution with dinner at Cantler's Riverside Inn, a crab house known for its steamed crabs and waterfront setting. After dinner, take a leisurely stroll along the Annapolis City Dock, soaking in the sights and sounds of the bustling waterfront.
Bedtime
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Annapolis Walking In App Audio Tour in Sailing Capital
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Annapolis Walking In App Audio Tour in Sailing Capital
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4.42Annapolis Harbor Cruise
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Annapolis Harbor Cruise
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Scavenger Hunts and Culinary Exploration
Morning
Enjoy a relaxed morning with brunch at Miss Shirley's Cafe, Annapolis, a local favorite for its Southern-inspired dishes. Afterward, engage in a fun and interactive activity with the Annapolis Private Scavenger Hunts. Solve clues, uncover hidden gems, and learn more about the city's history.
Afternoon
For a unique dining experience, have lunch at Vin909 Winecafe, a cozy spot known for its carefully curated wine selection and farm-to-table cuisine. Afterward, spend the afternoon exploring the artistic side of Annapolis at the Maryland Hall for the Creative Arts. Admire local artwork and maybe even catch a live performance.
Evening
Indulge in a memorable dinner at Lewnes' Steakhouse, a classic steakhouse with a long-standing reputation. After dinner, take a leisurely evening walk through the Historic Annapolis District, admiring the beautifully preserved colonial architecture and the soft glow of gas lamps.
Bedtime
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Historic Annapolis District
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Historic Annapolis District
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Ghost Tour and Farewell to Annapolis
Morning
For your last morning in Annapolis, enjoy a relaxed breakfast at Boatyard Bar & Grill, a waterfront restaurant known for its seafood dishes. Afterward, delve into the eerie side of the city with the Phantoms of Annapolis Ghost Walking Tour. Hear spooky tales and legends as you explore the haunted corners of Annapolis.
Afternoon
Have a leisurely lunch at Galway Bay Irish Pub, a lively spot with a great selection of Irish fare and drinks. Afterward, spend your afternoon at the William Paca House & Garden, a beautifully restored 18th-century mansion with stunning gardens. Learn about the life of William Paca, a signer of the Declaration of Independence.
Evening
End your Annapolis adventure with a farewell dinner at Chart House, a waterfront restaurant with spectacular views of the Chesapeake Bay. Raise a toast to your time in the Sailing Capital and savor a memorable dining experience. After dinner, take a leisurely walk along the Annapolis Waterfront, enjoying the twinkling lights and the gentle lapping of the water.
Bedtime
Find amazing hotels in Annapolis.
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4.67Phantoms of Annapolis Ghost Walking Tour
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William Paca House & Garden
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