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A Fun-Filled Guide to Things to Do in Annapolis

Steve Jennifer
Updated: Nov 28, 2023

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Annapolis, offers a captivating snapshot of the diverse activities this historic city has to offer. Renowned for its maritime legacy and colonial architecture, Annapolis invites visitors to stroll through its historic downtown, visit the U.S. Naval Academy, and enjoy sailing on the Chesapeake Bay. The city is also a haven for seafood lovers, especially for its Maryland blue crabs.

Quiet Waters Park provides a serene escape, while events like the United States Sailboat Show and the Annapolis Film Festival showcase the city's vibrant culture. Whether your interests lie in history, nature, or maritime activities, this guide to "Things to Do in Annapolis" ensures a trip filled with fascinating and memorable experiences.

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01. Sail into Sunset with Annapolis Cruises

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Annapolis Cruises offers a breathtaking opportunity to witness the Chesapeake Bay's beauty as the sun dips below the horizon. Their sunset cruises provide a perfect blend of romance and tranquility, making for an unforgettable evening. As you glide over the gentle waves, the sky transforms into a canvas of vibrant colors. The cruise not only offers stunning views but also a chance to learn about the bay's rich maritime history.

02. Catch a Show at Rams Head On Stage

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03. Taste Tradition at the Maryland State House

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The Maryland State House, steeped in history, is more than just an architectural marvel; it's a repository of America's rich political heritage. As the oldest state capitol in continuous legislative use, it offers visitors a journey through time. The building, with its grandeur and elegance, tells stories of past legislations and historic events. Guided tours provide insights into the building's significance and the pivotal role it played in shaping the nation. This visit is not just about viewing an old structure; it's about connecting with the chapters of American history.

04. Marvel at Maritime Wonders at the Naval Academy Museum

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The Naval Academy Museum presents a captivating collection of naval artifacts and exhibits that chronicle the United States Navy's history. From historic ship models to personal artifacts of naval heroes, the museum showcases a wide array of maritime treasures. The museum's collections are both educational and inspiring, offering a glimpse into the life at sea and the evolution of naval warfare.

05. Relax at Ego Alley with Waterfront Views

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Ego Alley, a nickname for the narrow waterway at the Annapolis City Dock, is a perfect spot for relaxation and people-watching. This bustling area is famous for its parade of boats, ranging from small sailing dinghies to opulent yachts. Visitors can sit by the water, enjoying the lively atmosphere and picturesque views. The surrounding area is filled with charming cafes and eateries, where one can grab a bite while observing the aquatic activity.

06. Indulge in a Sweet Treat at Annapolis Ice Cream Company

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Annapolis Ice Cream Company, located in the heart of downtown, is a haven for those with a sweet tooth. Their homemade ice cream, made with the freshest ingredients, offers a creamy and delightful experience. With a variety of flavors to choose from, each scoop is a testament to their commitment to quality and taste. The cozy ambiance of the shop, combined with the friendly staff, makes every visit enjoyable. Whether you prefer classic vanilla or adventurous flavors, their ice cream is a must-try for anyone visiting Annapolis.

07. Feel the Music with Annapolis Symphony Orchestra

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08. Experience Elegance at the Hammond-Harwood House

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The Hammond-Harwood House, a jewel of colonial architecture, offers a glimpse into 18th-century elegance and lifestyle. This well-preserved mansion, with its exquisite design and art collection, stands as a testament to the craftsmanship and artistic sensibilities of the era. The guided tours provide insights into the lives of its former inhabitants and the social customs of the time. The house's beautiful gardens are a tranquil retreat, perfect for a leisurely stroll.

09. Enjoy a Shake at Chick and Ruth's Delly

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10. Paddle the Day Away with Kayak Annapolis

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11. Step Back in Time at the William Paca House

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12. Savor Seafood at Boatyard Bar & Grill

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13. Discover Art at the Annapolis Arts District

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The Annapolis Arts District is a vibrant hub of creativity and culture. This lively area is home to galleries, studios, and theaters, showcasing the work of local and regional artists. Visitors can witness the artistic process in action, attend gallery openings, or enjoy live performances. The district's colorful murals and public art installations add to its charm, making it a visually stimulating place to explore.

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