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Coastal Maryland 5-Day Itinerary with Small Towns, Seafood, Beaches, and Nature Itinerary

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day 1

Historic Annapolis and Culinary Delights

Annapolis Itinerary - March 4

Morning. Begin your coastal Maryland adventure with a hearty breakfast at Iron Rooster, known for its delicious homemade pop tarts. After breakfast, take a self-guided audio tour with the Annapolis Walking In App Audio Tour in Sailing Capital to immerse yourself in the history and charm of the city. Visit the iconic landmarks including the Maryland State House and the United States Naval Academy.
Afternoon. For lunch, savor the fresh seafood at Cantler's Riverside Inn, a local favorite. Spend your afternoon exploring the quaint streets and shops of downtown Annapolis. Later, enjoy a relaxing cruise with the Annapolis Harbor Cruise to take in the scenic views of the waterfront and the Chesapeake Bay.
Evening. As the sun sets, dine at Chart House for a memorable waterfront dinner with panoramic views. Afterward, take a leisurely stroll along the Annapolis City Dock, soaking in the lively atmosphere and the postcard-perfect scenery.
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day 2

Ghostly Tours and Scenic Hunts

Annapolis Itinerary - March 5

Morning. Start your day with a guided Phantoms of Annapolis Ghost Walking Tour, where you'll hear eerie tales and explore the haunted history of the city. Afterward, grab a coffee and light breakfast at Miss Shirley's Cafe, Annapolis.
Afternoon. Have an adventurous afternoon with an entertaining Annapolis Private Scavenger Hunts. This interactive experience will lead you to hidden gems and historical sites in the city. For a late lunch, head to The Point Crab House & Grill for some of the best crab cakes in Annapolis.
Evening. Relax and enjoy the evening at Rams Head Tavern Annapolis, known for its great live music and casual pub atmosphere. Savor a variety of local brews and end the night with a delicious dinner and a show.
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day 3

Cultural Immersion and Upscale Dining

Annapolis Itinerary - March 6

Morning. Start your day with a visit to the U.S. Naval Academy Museum, where you can explore the history of the Navy. Afterward, enjoy a delightful brunch at Metropolitan Kitchen & Lounge, known for its vibrant atmosphere and diverse menu.
Afternoon. Spend your afternoon at the Historic London Town and Gardens, immersing yourself in the area's colonial history and beautiful landscapes. For a late afternoon snack, visit Vin909 Winecafe and indulge in some fine wine and artisanal cheese.
Evening. For dinner, experience the elegant ambiance and exquisite steaks at Lewnes' Steakhouse, a local landmark. Afterward, take a leisurely stroll through the charming streets of the historic district, enjoying the architectural beauty of Annapolis at night.
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day 4

BWI Transfer and Dynamic Baltimore

Annapolis Itinerary - March 7

Morning. Today, take advantage of the BWI Airport Transfer to Baltimore or Washington DC to explore the vibrant city of Baltimore. Upon arrival, have a delightful breakfast at Blackwall Hitch Annapolis.
Afternoon. Spend your afternoon visiting the Baltimore Inner Harbor, where you can explore the historic ships, visit the National Aquarium, and enjoy the bustling waterfront. For lunch, indulge in the Latin flavors at Paladar Latin Kitchen & Rum Bar.
Evening. As the day turns to night, experience the lively and diverse culinary scene of Baltimore. Enjoy a dinner at Harry Browne's Restaurant, known for its sophisticated menu and elegant setting. Afterward, explore the city's vibrant nightlife before returning to Annapolis.
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day 5

Seaside Relaxation and Farewell Feasts

Annapolis Itinerary - March 8

Morning. Begin your final day with a visit to the serene Sandy Point State Park. Enjoy the sandy beaches, take a dip in the Chesapeake Bay, or engage in some recreational activities. For breakfast, pack a picnic or grab some to-go treats from Galway Bay Irish Pub.
Afternoon. After soaking up the sun, head to Quiet Waters Park for a leisurely afternoon. Explore the scenic trails, rent a kayak, or simply relax by the tranquil waters. For a late lunch, enjoy the casual atmosphere and fresh seafood at Boatyard Bar & Grill.
Evening. Conclude your coastal Maryland journey with a farewell dinner at O'Learys Seafood Restaurant, where you can indulge in the finest local catches and raise a glass to the memories made. Reflect on your trip as you enjoy the warm hospitality and hospitality of Annapolis.
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