Historic Annapolis and Beyond: 5-Day Maryland Adventure Itinerary

Fuel up for the day with breakfast at Stan & Joe's Saloon. Then, engage in a fun and interactive morning with the Annapolis Private Scavenger Hunts. Explore the city in a unique way while solving clues and uncovering hidden gems.

Enjoy a casual lunch at Boatyard Bar & Grill, known for its nautical atmosphere and fresh seafood. Post-lunch, visit the William Paca House & Garden for a guided tour of this beautifully restored 18th-century home and its stunning gardens.

Experience the vibrant nightlife of Annapolis at Level a small plates lounge. Indulge in a variety of small plates and cocktails while enjoying the sophisticated ambiance. Cap off the evening with live music at Rams Head On Stage, a renowned local venue.

Begin your day with a visit to the Chesapeake Bay Maritime Museum in nearby St. Michaels. Explore the maritime history and enjoy the waterfront setting. For breakfast, try the artisanal pastries at Metropolitan Kitchen & Lounge.

Have a leisurely lunch at Armadillos Restaurant, known for its southwestern cuisine. Afterward, return to Annapolis and spend the afternoon browsing the galleries and boutiques along Maryland Avenue and State Circle, a charming historic district.

Dine at McGarvey's, a local favorite with a cozy atmosphere. Then, enjoy a performance at the Annapolis Shakespeare Company or catch a movie at the Bow Tie Cinemas Annapolis Mall 11 for a relaxing end to the day.

Take a day trip to nearby Baltimore. Start with breakfast at Federal House Bar & Grille in the heart of Annapolis. Then, head to Baltimore's iconic Inner Harbor. Explore the attractions, visit the National Aquarium, and enjoy the bustling waterfront.

For lunch, try the innovative dishes at Middleton Tavern, known for its historic charm and excellent cuisine. Afterward, you can choose to visit one of Baltimore's many museums, such as the Baltimore Museum of Art or the Walters Art Museum.

Return to Annapolis for a relaxing dinner at Pusser's Caribbean Grille - Annapolis Restaurants, where you can enjoy waterfront views and island-inspired dishes. End the evening with a drink at Red Red Wine Bar + Bistro, known for its extensive wine selection.

Begin with a hearty breakfast at Davis' Pub, a local spot with a welcoming atmosphere. Then, visit the Historic London Town and Gardens, a short drive from Annapolis. Explore the historic area and enjoy the beautiful gardens by the South River.

For lunch, head to Dock Street Bar & Grill, located in the heart of Annapolis. Afterward, spend the afternoon at the Anne Arundel County War of 1812 Sites, visiting historic sites and learning about the county's role in the War of 1812.

Conclude your Annapolis journey with a memorable dinner at Wild Country Seafood, where you can enjoy fresh seafood in a relaxed setting. After dinner, take a walk along the Annapolis City Dock and soak in the waterfront views, reflecting on your time in this historic city.