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Roam Around

Annapolis Adventure: History, Haunts, and Culinary Delights Itinerary

Last updated: 2024 Jun 14

Historic Annapolis and Culinary Delights

Morning

Start your day with a delightful breakfast at Middleton Tavern, a historic spot in Annapolis. Afterward, immerse yourself in the city's rich history with a visit to the United States Naval Academy, where you can explore the campus and learn about the history of the Navy.

Afternoon

For lunch, head to Galway Bay Irish Restaurant and Pub for some traditional Irish fare. Afterward, take a leisurely stroll through the charming streets of downtown Annapolis and visit the Maryland State House, the oldest state capitol still in continuous legislative use.

Evening

Enjoy a relaxing dinner at Level a small plates lounge, where you can sample a variety of dishes in a cozy atmosphere. Afterward, take a ghostly walking tour with the Phantoms of Annapolis Ghost Walking Tour and hear spooky tales of the city's past.

Bedtime

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Scavenger Hunts and Seafood Sensations

Morning

Fuel up for the day with breakfast at Reynolds Tavern and 1747 Pub, a historic spot with a charming ambiance. Then, embark on an exciting Annapolis Private Scavenger Hunts to discover hidden gems and local secrets around the city.

Afternoon

After the scavenger hunt, enjoy a seafood lunch at O'Brien's Oyster Bar & Seafood Tavern, known for its fresh oysters and maritime atmosphere. Spend the rest of the afternoon exploring the Annapolis Maritime Museum to learn about the area's maritime heritage.

Evening

Dine at Pusser's Caribbean Grille - Annapolis Restaurants for a taste of the islands right in Annapolis. After dinner, relax with a drink at Red Red Wine Bar + Bistro, which offers an extensive selection of wines and a sophisticated ambiance.

Bedtime

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Sailing, Shopping, and Sunset Views

Morning

Enjoy a breakfast with a view at West End Grill and then head to the Annapolis City Dock to take in the sights and maybe even catch a glimpse of the boats. If you're interested, consider a morning sail on the Schooner Woodwind Sailing Cruises to experience the beauty of the Chesapeake Bay.

Afternoon

For lunch, visit Metropolitan Kitchen & Lounge for a modern dining experience. Afterward, spend your afternoon exploring the boutiques and shops along Main Street, where you can find unique souvenirs and local treasures.

Evening

Conclude your Annapolis adventure with a memorable dinner at Boatyard Bar & Grill, a local favorite known for its seafood and nautical decor. Afterward, take a leisurely stroll to Quiet Waters Park and enjoy the serene natural setting as the sun sets on your final day in Annapolis.

Bedtime

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