Annapolis stands out as a prime destination for anyone interested in American history. Its well-preserved architecture, significant landmarks, and centuries-old stories make it a living history book. What makes it particularly appealing for historical tours is the city’s role as the birthplace of American independence—think about the Maryland State House, where the Treaty of Paris was signed, and the spot where George Washington resigned his commission. Plus, its charming waterfront and stately colonial homes add a picturesque backdrop to every story. Among the options available, we especially appreciate tours that blend history with local flavor, like the Annapolis Historic Walking Tour at Harbor and Naval Academy, which offers a rich, guided exploration of the city’s most iconic sites.
Whether you’re after a deep dive into naval history, enjoy lively pub stories, or want a spooky twist, Annapolis has something to fit different interests. We’ve rounded up the top four options, from walking explorations to food and ghost tours, to help you choose the best experience for your visit.
1. Annapolis Historic Walking Tour at Harbor and Naval Academy
At number 1 on our list, the Annapolis Historic Walking Tour at Harbor and Naval Academy offers a comprehensive two-hour stroll through the city’s most significant sites. Priced at $235 per group (up to 10 people), this tour is perfect for families or small groups who want an in-depth look at Annapolis’ past. The tour explores Georgian mansions, the Maryland State House—America’s oldest state capitol still in legislative use—and the U.S. Naval Academy with its striking neoclassical architecture. Guides like Michael, who are highly praised, bring stories of George Washington’s resignation, the Treaty of Paris, and local lore to life, often customizing the experience based on the group’s interests. You’ll visit Ego Alley, the Naval Academy Chapel, Hammond-Harwood House, and finish at the historic State House, giving you a well-rounded understanding of the city’s history.
The appeal of this tour lies in its rich storytelling and focus on key moments in American history. It’s suitable for history lovers who want a manageable pace and expert narration. Plus, the included sites are all photogenic and full of stories, making this experience both educational and enjoyable.
Bottom line: This tour offers exceptional value for those seeking a guided, personalized experience with a focus on historic landmarks and storytelling that captures the essence of Annapolis.
2. Historic Annapolis Food Tour
For around $80 per person, the Historic Annapolis Food Tour combines culinary delights with local history over approximately three and a half hours. It’s designed for travelers who want to taste their way through the city while learning lesser-known stories behind Annapolis’ historic sites. The tour includes visits to downtown restaurants, some of which have historic connections—like taverns where Washington, Jefferson, and Franklin once dined. You’ll sample dishes at each stop, making the tour both a gastronomic adventure and a cultural lesson. Guides like Carolyn are praised for their knowledge of both food and history, making the experience engaging and authentic.
What sets this tour apart is its relaxed pace and the chance to enjoy delicious local bites while uncovering stories you won’t find in guidebooks. It’s a good choice for foodies or families looking for a more casual way to explore. The stops outside Hammond-Harwood House add a touch of architectural history, enriching the food experience with context.
Bottom line: If you prefer combining history with food and want a leisurely, tasty afternoon, this tour provides a memorable, multisensory experience at a reasonable price.
3. Hidden History Pub Crawl of Historic Annapolis
At just $30 per person, the Hidden History Pub Crawl of Historic Annapolis offers a fun, informal way to explore the city’s lesser-known stories. Lasting around two hours, the tour visits three historic taverns, each with its own story—such as which was a popular brothel or which founding father was chased out. The tour is ideal for those who enjoy a laid-back atmosphere and some local spirits, as most bars offer drink specials for participants. The guide shares intriguing tales of Annapolis’ past, including stories about the city’s saloons and clandestine activities.
This experience is less about grand landmarks and more about uncovering quirky, surprising stories behind the city’s taverns. It’s perfect for travelers who enjoy a lively, social atmosphere with a bit of history on the side. Be prepared for a spirited evening, and remember that this tour isn’t designed for those seeking a quiet, contemplative experience.
Bottom line: For those interested in local tavern history and lively storytelling, this pub crawl offers a relaxed way to connect with Annapolis’ more colorful past.
$30.00 per person
4. Annapolis: Historic Ghost Tour
Price at $30 per person and lasting about 90 minutes, the Annapolis Ghost Tour is ideal for travelers who love a spooky story. Led by period-dressed guides, this tour covers four centuries of supernatural tales and eerie occurrences. Highlights include stories about a jilted bride haunting a landmark, and why colonial residents once picnicked in cemeteries. It’s a lighter, storytelling-driven experience that relies on well-documented events rather than scares, making it suitable for families or those curious about the city’s darker side.
What makes this tour stand out is the atmospheric storytelling and the focus on documented hauntings rather than ghost-hunting. It’s a good option for evening entertainment, especially if you’re interested in Annapolis’ more mysterious history.
Bottom line: If you enjoy tales of the supernatural and want an engaging, spooky evening, this ghost tour offers an entertaining way to see a different side of Annapolis’ past.
$30 per person
How to Choose the Right Tour
When selecting a tour, consider your interests, schedule, and budget. If you’re after a comprehensive understanding of Annapolis’ role in American history, the Annapolis Historic Walking Tour offers expert storytelling and access to key landmarks. For a more relaxed, taste-focused experience, the Historic Annapolis Food Tour combines food sampling with history, perfect for foodies. If you want a lively, social night, the Hidden History Pub Crawl provides quirky stories and drinks in historic taverns. Lastly, for a fun evening with a spooky twist, the Annapolis Ghost Tour is a great choice.
Think about how much time you have—most tours range from 1.5 to 3.5 hours—and whether your interest lies in architecture, food, lively taverns, or supernatural stories. Booking early is advisable, especially during peak seasons, to secure your preferred date.
Final Thoughts
Annapolis offers a surprising variety of historical tours that cater to different interests and travel styles. For a thorough, guided exploration, the Harbor and Naval Academy Tour stands out. If you’re looking to combine gastronomy and history, the Food Tour delivers both in a friendly, relaxed package. For a more spirited, social experience, the pub crawl adds a humorous twist to history, while the ghost tour offers a fun, spooky peek into Annapolis’ darker stories.
No matter which you choose, booking ahead ensures a spot in these popular experiences. Annapolis’s historic charm is waiting—so pick your tour, and get ready to step into the storybook city that played a key role in American history.
Happy exploring!