Annapolis is a city that lends itself beautifully to walking tours. With its compact historic center, lively waterfront, and storied military and political past, exploring on foot is the best way to soak in its charm. Whether you’re into ancient architecture, military history, or spooky tales, Annapolis offers something for every interest. For example, the Annapolis Historic Walking Tour at Harbor and Naval Academy provides a detailed look at the city’s most iconic sites, including the U.S. Naval Academy and the Maryland State House. We especially appreciate how this tour combines fascinating storytelling with visits to key landmarks—making history feel alive.
While historic sites are the highlight, Annapolis also offers more unusual experiences, like the Ghost Tour, which takes you into the city’s darker tales of hauntings and mysterious happenings. For those who prefer interactive fun, the Scavenger Hunt turns sightseeing into a game, perfect for families or groups looking for an active, engaging way to explore.
1. Annapolis Historic Walking Tour at Harbor and Naval Academy
At number one, this Annapolis Historic Walking Tour at Harbor and Naval Academy scores a perfect 5.0 rating based on 21 reviews. It’s a well-rounded, 2-hour exploration that covers some of the city’s most significant sites, all with a knowledgeable guide. The tour kicks off at Ego Alley, where you’ll get a scenic view of the waterfront and learn about Annapolis’s origins. From there, you’ll visit the U.S. Naval Academy, one of the city’s crown jewels, experiencing the impressive campus and hearing stories of its training role for future Navy officers. The Naval Academy Chapel offers stunning neoclassical architecture and maritime stained glass, while the Hammond-Harwood House introduces you to Annapolis’s colonial grandeur. Finally, the tour concludes at the Maryland State House, the oldest legislative building still in continuous use in the U.S.
What makes this tour stand out is its rich blend of history, architecture, and patriotism. The guide’s engaging storytelling about figures like General Washington and the Treaty of Paris adds depth to your walk. Guests consistently praise the guide’s knowledge, flexibility, and friendliness. The $235 fee covers a small group (up to 10), making for an intimate experience—great for history enthusiasts or visitors wanting a thorough overview. The only downside is the price might seem high for some, but the quality and depth of the stories make it worth considering.
Bottom Line: This tour is perfect if you want a comprehensive, well-led exploration of Annapolis’s most famous sites combined with personal attention.
2. The Original Walking Ghost Tour by Annapolis Ghost Tours
For those intrigued by the spooky side of Annapolis, the Ghost Tour offers an hour and a half of spine-tingling stories in the historic downtown district. Rated 4.0 based on 27 reviews, this tour takes you into the city’s oldest neighborhoods and haunted graveyards while sharing tales of ghostly encounters and mysterious happenings. Your guide recounts stories of paranormal activity rooted in the city’s past, with visits to sites like the Maryland State House and other haunted locations.
What makes this tour unique is its focus on Annapolis’s dark side, blending history with ghostly legends. The tour is lively, with a friendly guide who makes the supernatural tales come alive. It’s ideal for history lovers who enjoy a good scare or groups that want a fun, different way to spend an evening. The price is free, which makes it an excellent budget option, though you’ll want to tip your guide. Since it’s only 1 hour and 30 minutes, it’s perfect for a quick evening outing or for those pressed for time. Some reviews mention the guide’s engaging storytelling and the fun atmosphere, making it a memorable experience despite the shorter duration.
Bottom Line: If you’re curious about Annapolis’s haunted past and enjoy ghost stories, this tour provides a fun, spooky twist on the city’s history.
3. Annapolis Scavenger Hunt Interactive Walking Tour
For travelers who like a challenge and some fun competition, the Annapolis Scavenger Hunt offers an interactive way to explore the city. Priced at $34.99 per group (up to 15), this 2-hour experience combines riddles, clues, and photo challenges to uncover Annapolis’s secrets. As you walk through the historic streets, you’ll learn about Princess Anne, Abraham Lincoln, and Duke Ellington, while also discovering architectural marvels and learning about Maryland’s oldest living residents.
What sets this tour apart is its game-like format, perfect for families, friends, or anyone wanting to turn sightseeing into a lively competition. It’s flexible—you can start anytime and go at your own pace, making it suitable for all fitness levels and schedules. Since there are no reviews yet, it’s a new option, but its format promises an engaging experience. It’s best suited for active travelers who enjoy problem-solving and fun challenges. Keep in mind that it’s not as educational or historical as the other tours but offers a unique way to see the sights through riddles and puzzles.
Bottom Line: This is an excellent choice if you want an interactive, family-friendly experience that makes exploring more fun and less formal.
$34.99 per group (up to 15)
How to Choose the Right Walking Tour in Annapolis
When selecting a walking tour, consider your interests, budget, and how much time you want to spend. If you’re after a deep dive into Annapolis’s history and architecture, the Harbor and Naval Academy Tour offers a detailed, guided experience. For a spooky twist, the Ghost Tour is perfect. And if you prefer a fun, interactive approach, the Scavenger Hunt makes sightseeing feel like a game.
Think about your group’s interests—history lovers may prefer the more comprehensive tour, while families or groups who want fun and activity might enjoy the scavenger hunt. Budget-wise, the ghost tour is free, whereas the historic tour offers an in-depth experience for a higher price. For best results, book early, especially in peak season, and plan your tour around the time of day that suits your interests—morning light is great for photos, while evening ghost stories add a thrill.
Final Thoughts
Annapolis’s compact layout makes it an ideal city for walking tours, whether you’re into history, ghost stories, or interactive adventures. The Annapolis Historic Walking Tour stands out for its depth and guided storytelling, perfect for history enthusiasts. If you’re in the mood for something spooky, the ghost tour offers a fun, atmospheric experience. And for a more playful approach, the scavenger hunt keeps everyone engaged with riddles and photo challenges.
Different travelers will find their perfect match here: history buffs will love the deep dive into Annapolis’s past, while families and groups seeking fun will appreciate the scavenger hunt. Budget-conscious visitors can enjoy the ghost tour for free, and those wanting a personalized, small-group experience will find the historic walk ideal. Whatever your choice, booking in advance is wise to secure your spot in this charming city.
Enjoy your time in Annapolis, and don’t forget—walking is the best way to truly experience this historic Maryland town.