The 2 Best Historical Tours in Annapolis
Annapolis’s charm isn’t just in its scenic harbor or colonial architecture—its history runs deep, woven into every brick and bay. The city’s fascinating past includes being the site where the Treaty of Paris was signed and where George Washington resigned his commission as general. These stories are best experienced firsthand, and luckily, you can do so with tours that blend walking, history, and local flavor. Whether you want a quick walk through iconic sites or a more leisurely taste of Annapolis’s culinary history, there’s a tour that will suit your style.
What makes Annapolis stand out is its preserved architecture, storied landmarks, and the Naval Academy’s daily pageantry. These tours are designed to bring alive these details with expert guides and a focus on authentic experiences. Ready to step into the past? Keep reading to find your perfect historical adventure.
Quick Overview
Our list highlights two standout options for exploring Annapolis’s history: a guided walking tour that covers landmarks like the Maryland State House and Naval Academy, and a food-focused tour combining historic insights with tastings from notable local eateries. Both tours offer engaging stories, excellent reviews, and a chance to see the city from different angles. For more details on each, visit the respective tour pages: Annapolis Historic Walking Tour at Harbor and Naval Academy and Historic Annapolis Food Tour.
If you want an in-depth introduction to Annapolis’s most iconic sites, this 2-hour walking tour is a perfect choice. Priced at $235 for a group of up to 10 people, it offers personalized attention from an experienced guide. The tour hits the highlights: from the picture-perfect Ego Alley to the Majestic Maryland State House, the oldest state capital still in legislative use since 1772.
What sets this tour apart is its focus on key moments in American history. You’ll stand where General Washington resigned his commission and learn about the Treaty of Paris that ended the Revolutionary War. The Naval Academy’s imposing architecture and the Crypt of John Paul Jones are included, giving you a sense of the city’s maritime importance. The Hammond-Harwood House offers a glimpse into Annapolis’s colonial heyday.
Guests consistently praise the guide’s depth of knowledge—one reviewer called Michael “an excellent guide” who was accommodating even in bad weather. The tour’s value lies in its rich storytelling and access to sites that define Annapolis. A great pick for history lovers wanting a compact, well-rounded experience.
Bottom Line: A highly rated, engaging tour that covers the core of Annapolis’s history and architecture, perfect for those who want a detailed, personal introduction.
2. Historic Annapolis Food Tour
For about $80 per person, this food tour offers a lively way to explore Annapolis’s past and present. Spanning roughly 3.5 hours, it combines historic site visits with tastings at downtown restaurants, some with notable histories of their own—like a tavern once frequented by Washington, Jefferson, and Franklin.
What makes this tour stand out is the blend of culinary delights and storytelling. You’ll visit landmarks like the Hammond-Harwood House and learn interesting facts about Annapolis’s colonial days while enjoying dishes from local eateries. This approach appeals to travelers who want to experience the city through taste and tales, rather than merely walking through historic sites.
Guests highlight how well the guide, Carolyn, connects stories with the food: “The four food stops were excellent,” one reviewer notes, “and Carolyn’s knowledge about Annapolis and its history made it special.” It’s a relaxed, interactive way to discover the city’s lesser-known stories while satisfying your appetite.
Bottom Line: An engaging, flavorful way to see Annapolis, ideal for those who prefer a leisurely pace and enjoy combining history with local cuisine.
How to Choose
Deciding between these tours depends on your interests and schedule. If you prefer a compact, comprehensive look at the city’s key landmarks and history, the Annapolis Historic Walking Tour offers a detailed narrative in just a couple of hours. It’s suited for travelers who want to maximize their time and get a solid grounding in Annapolis’s significance.
If your goal is to combine history with good food and social fun, the Historic Annapolis Food Tour provides a relaxed, flavorful experience that also reveals some of the city’s lesser-known stories. Ideal if you want a more casual, immersive taste of local culture.
Consider your budget, time availability, and whether you prefer a walking-focused experience or a mix of bites and stories. Booking early is recommended, especially during peak seasons, to secure spots on these popular tours.
Final Thoughts
Both tours offer authentic insights into Annapolis’s past, whether through a focused walk of historic landmarks or a food-filled exploration. The walking tour is best for history buffs craving a detailed narrative, while the food tour suits those wanting a leisurely, tasty adventure with cultural flavor.
For travelers looking for a quick, in-depth overview, the Annapolis Historic Walking Tour delivers a compact dose of history and architecture. Meanwhile, the Historic Annapolis Food Tour is perfect for those who enjoy learning about a city through its food and stories behind the eateries.
No matter which option you choose, booking early ensures you won’t miss out on these memorable experiences. Annapolis’s blend of history, architecture, and local flavors makes for a rewarding visit—so get ready to walk, taste, and learn about this charming Chesapeake Bay town.