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Culinary Delights and Historic Sights in Annapolis, Maryland Itinerary

Last updated: 2024 Jun 14

Colonial Charm and Waterfront Wonders

Morning

Begin your Annapolis adventure with a delightful breakfast at Reynolds Tavern and 1747 Pub, where you can savor a historic ambiance along with your meal. Post breakfast, immerse yourself in the city's history with a visit to the iconic United States Naval Academy. Take a guided tour to explore the beautiful campus and learn about the history of the Navy.

Afternoon

For lunch, head to Middleton Tavern, one of the oldest continuously operating taverns in America. After a satisfying meal, take a leisurely stroll along the Annapolis City Dock. Enjoy the maritime atmosphere, visit the Annapolis Maritime Museum, and take in the views of the boats and the harbor.

Evening

As the sun sets, dine at Pusser's Caribbean Grille, where you can enjoy a taste of the islands right in Annapolis. After dinner, take a relaxing cruise with Annapolis Sailing Cruises to end your day with the gentle breeze and the beautiful sights of the city from the water.

Bedtime

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Historic Homes and Culinary Delights

Morning

Start your day with a visit to the Hammond-Harwood House, an architectural gem from the 18th century. After exploring the house, enjoy a brunch at Metropolitan Kitchen & Lounge, known for its creative dishes and vibrant atmosphere.

Afternoon

Post brunch, take a guided tour of the William Paca House and Garden. This beautifully restored 18th-century home and garden provide a glimpse into the life of the early American elite. For a late afternoon snack, head to Level a small plates lounge and indulge in a variety of small bites and refreshing drinks.

Evening

For dinner, experience the cozy and elegant ambiance of Galway Bay Irish Restaurant and Pub. Afterward, if you're in the mood for some live music, Rams Head On Stage is just a short walk away. Enjoy a performance at this intimate venue to cap off your evening.

Bedtime

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Art, Antiques, and Annapolis Eats

Morning

Begin your day with a visit to the Anna Point Marina, where you can enjoy the serene morning waters and perhaps even take a kayak or paddleboard out for a bit. Afterward, grab a coffee and light breakfast at Boatyard Bar & Grill to fuel up for the day.

Afternoon

Spend your afternoon exploring the Annapolis Collection Gallery, which features a diverse range of art and antiques. For lunch, head to Dock Street Bar & Grill and enjoy their waterfront dining experience, with views of Ego Alley and the Annapolis Harbor.

Evening

As the day winds down, treat yourself to a fine dining experience at Julep Kitchen & Bar, known for its innovative Southern cuisine. After dinner, take a leisurely walk through the historic streets of Annapolis, enjoying the architecture and the charm of the city at night.

Bedtime

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Annapolis Nature and Local Flavors

Morning

Start your day with a hearty breakfast at Armadillos Restaurant, known for its Tex-Mex and Southwestern cuisine. After breakfast, head to the Quiet Waters Park for a morning of outdoor exploration. The park offers walking trails, serene water views, and beautiful gardens.

Afternoon

For lunch, visit Federal House Bar & Grille, a local favorite with a diverse menu. Afterward, take a short drive to the Sandy Point State Park for an afternoon of beach relaxation. Enjoy the Chesapeake Bay's sandy shores and maybe even take a dip if the weather permits.

Evening

Conclude your day with a dinner at McGarvey's, a classic Annapolis spot with a warm and welcoming atmosphere. If you're up for some post-dinner entertainment, Annapolis Summer Garden Theatre might have a lively performance to enjoy under the stars.

Bedtime

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Annapolis Farewell and Nearby Excursions

Morning

Enjoy a final breakfast in Annapolis at McGarvey's, savoring the local flavors one last time. After breakfast, consider taking a day trip to the nearby city of Baltimore, where you can explore attractions like the Baltimore Inner Harbor, the National Aquarium, and enjoy the diverse culinary scene.

Afternoon

For lunch, indulge in the flavors of West End Grill, known for its contemporary American cuisine. Afterward, if you prefer a more relaxed afternoon, consider visiting the charming town of St. Michaels, just a short drive from Annapolis. Explore the Chesapeake Bay Maritime Museum and enjoy the waterfront views.

Evening

Return to Annapolis for your final evening and dine at Red Red Wine Bar + Bistro, where you can raise a glass to a wonderful trip. Reflect on your Annapolis adventures and perhaps take a twilight stroll through the city, visiting any favorite spots one last time.

Bedtime

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