Annapolis is a city that rewards exploration on foot. Its charming streets, historic buildings, and scenic waterfront are best experienced at a leisurely pace, allowing you to soak in the atmosphere and uncover stories behind every corner. A walking tour in Annapolis offers a chance to see iconic landmarks like the Maryland State House and U.S. Naval Academy while hearing captivating tales from knowledgeable guides. Whether you’re interested in the city’s revolutionary past or spooky legends, Annapolis has a walking tour tailored to your interests.
The city’s compact layout makes it ideal for exploring on foot. You can stroll through historic neighborhoods, admire Georgian manors, and visit lively harbors, all while gaining insights that deepen your appreciation for this lively Maryland port. The two tours highlighted here offer contrasting experiences: one immerses you in the city’s historic sights, and the other adds a spooky twist with ghost stories. Both are highly rated and offer a distinct way to understand Annapolis’s character.
Quick Overview
Below, we’ve outlined the best walking tours in Annapolis, ranging from historic explorations to ghostly encounters. Each tour provides a unique perspective on the city’s past and present, with detailed descriptions and reviews to help you choose the right fit. For more details on each tour, visit their respective pages: Annapolis Historic Walking Tour at Harbor and Naval Academy and The Original Walking Ghost Tour by Annapolis Ghost Tours.
At number 1, the Annapolis Historic Walking Tour at Harbor and Naval Academy offers a well-rounded introduction to the city’s most famous sites. It lasts about 2 hours and costs $235 per group (up to 10 people), making it a good choice for families or small groups wanting an intimate experience. The tour hits key landmarks like Ego Alley, where you can see the waterfront and hear about Annapolis’s beginnings, and the U.S. Naval Academy, which is a symbol of maritime excellence. The tour also includes a visit to the Naval Academy Chapel, renowned for its maritime stained glass, and the Hammond-Harwood House, a stunning example of colonial architecture.
What makes this tour stand out is the depth of historical detail and the personal touch of the guide, Michael, who is praised for his knowledge and engaging style. Reviews consistently mention how accommodating he was, even in bad weather, and how his storytelling makes history come alive. The tour culminates at the Maryland State House, the oldest state capital still in legislative use, where you’ll learn why Annapolis was the first peacetime U.S. capital.
Bottom Line: Perfect for history lovers wanting a rundown, this tour offers an engaging, well-organized experience with top-notch reviews and a small-group feel.
2. The Original Walking Ghost Tour by Annapolis Ghost Tours
Ranking second is The Original Walking Ghost Tour by Annapolis Ghost Tours, which is ideal for those interested in the city’s darker side. This 1.5-hour tour, free of charge, explores the oldest, most haunted neighborhood, highlighting sites like haunted graveyards and historic buildings tied to spooky legends.
What makes this tour special is its focus on stories of paranormal activity intertwined with real history. Your guide shares eerie tales of spirits that allegedly still linger, bringing the city’s past to life in a different way. The tour is especially suited for those who enjoy a bit of fun and fright alongside historical context, making it an entertaining evening activity.
Reviewers note Sarah, the guide, as very knowledgeable and engaging, with a fun attitude that keeps the tour lively. This tour is an excellent choice if you’re after a short, fun experience that combines local legends with history, without the cost of a private guide.
Bottom Line: Best for night owls and those who enjoy ghost stories, this tour provides a memorable, spooky twist on Annapolis’s history.
How to Choose Between the Tours
When deciding between these two Annapolis walking tours, consider what kind of experience you’re after. If your main goal is to understand the city’s historic sites and enjoy a personalized guided experience, the Annapolis Historic Walking Tour at Harbor and Naval Academy offers a detailed look at landmarks like Ego Alley, the State House, and the Naval Academy. It’s well-suited for history buffs, small groups, and travelers who appreciate in-depth storytelling.
On the other hand, if you’re intrigued by ghost stories and want a shorter, more playful experience, the Ghost Tour provides a fun, spooky alternative. It’s perfect for evening outings, affordable, and brings the city’s haunted reputation to life with colorful tales.
Think about your budget, time availability, and interests. For detailed planning, check the tour websites for booking tips and best times to visit — both tours run year-round but may have seasonal schedules.
Final Thoughts
Both tours provide authentic ways to experience Annapolis, whether through its historic landmarks or ghostly legends. The Harbor and Naval Academy Tour is great for history lovers and small-group intimacy, while the Ghost Tour offers a fun, spooky evening for those who enjoy tales of spirits and mystery.
For travelers with limited time, consider doing the historic tour during the day to soak up the city’s architecture and history, then return at night for the ghost walk if you’re into supernatural stories. Booking early is always a good idea, especially in peak season, to secure a spot on these popular tours.
Embrace the chance to see Annapolis from different angles—whether through the lens of history or haunting tales, you’re sure to leave with memorable stories to tell.