Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Discover Annapolis's historic waterfront and Naval Academy on a 2-hour private walking tour led by expert guide Michael, with highlights like the Maryland State House and Hammond-Harwood House.

This private walking tour in Annapolis, USA, offers a comprehensive 2-hour exploration of the city’s most iconic sites, all for $235 per group (up to 10 people). Led by Michael, a knowledgeable and personable guide, the tour is praised for its engaging storytelling and flexible approach, making it ideal for history buffs, families, and anyone interested in American heritage.
The tour includes no ticket fees for stops and features excellent photo opportunities along the waterfront and historic buildings. The experience is best booked at least 34 days in advance, ensuring you secure a spot with a proven guide who has received perfect reviews from a variety of visitors.
While the tour is quite rich in content, it’s designed to be accessible and flexible, with options to customize based on your interests. The tour’s overall 5-star rating reflects its strong reputation for engaging guides and compelling storytelling, especially from Michael, whose enthusiasm and local knowledge shine throughout.

If you're drawn to exploring Annapolis on foot, we've looked into these other walking experiences
The tour begins at 25 Market Space in Annapolis, a centrally located spot near public transportation options. The meeting point is convenient for those arriving by bus or walking from nearby accommodations. The tour typically lasts around 2 hours, and the guide ensures a relaxed pace, allowing ample time to enjoy each stop and take photos.
Arrival at the starting point is simple, and the tour ends back at the same location, making it easy for participants to plan their day afterward. Since there’s no need for tickets at each stop, the focus stays on the experience and storytelling.

The tour kicks off with Ego Alley, where the waterfront and Severn River meet the Chesapeake Bay. This scenic spot offers iconic views and a chance to learn about Annapolis’s foundational history. Visitors see bustling boats, historic waterfront buildings, and gain insight into the city’s maritime origins.
This stop is also ideal for capturing photos of historic boats against the water backdrop. The guide shares stories of Annapolis’s early days, setting the tone for the city’s blend of maritime charm and historical significance.

Next, the tour visits the U.S. Naval Academy, a revered institution training future Navy and Marine Corps officers. The campus’s architecture exudes dignity and tradition, with views of the water reflecting the academy’s maritime focus.
The Naval Academy Chapel is included, showcasing neoclassical architecture and beautiful maritime-themed stained glass. Visitors also see the Crypt of John Paul Jones, a pivotal figure in American naval history, and learn about the academy’s role in shaping U.S. military leaders.

The tour then moves to the Hammond-Harwood House, a prime example of late colonial architecture and one of Annapolis’s most beautiful historic homes. Built during the “Golden Age” of colonial Annapolis, its façade offers a glimpse into the city’s prosperity in the 18th century.
The guide shares stories of the house’s history and its significance, adding context to the city’s colonial past. This stop also provides excellent photo opportunities due to its well-preserved façade and charming surroundings.

One of the tour’s highlights is the Maryland State House, the oldest state capital still in legislative use since 1772. It is also notable as the first peacetime capital of the United States.
Visitors learn why this building is historically significant, including the room where George Washington resigned his commission as Commander-in-Chief. The State House’s architecture and historical role make it a must-see for those interested in early American history.

The tour includes a brief visit to St. John’s College, founded in 1696, making it the third-oldest higher education institution in the United States. The college is renowned for its Great Books liberal education and colonial architecture.
The guide shares details about the college’s notable traditions, such as the “Annapolis Cup”, and its role in American educational history. The stop provides a peaceful setting to appreciate colonial-era campus buildings.

Throughout the tour, Michael shares personal and family stories, bringing a personal touch to the historic sites. His storytelling style is praised for being clear, engaging, and adaptable to the group’s interests.
Photograph opportunities are plentiful, especially along the waterfront and at historic buildings, making it easy to capture memories of the day. The tour is also flexible, with the option to customize stops or focus on particular interests upon request.
The tour is suitable for most travelers, including those with limited mobility, as the stops are primarily walking and involve outdoor viewing. Participants are advised to avoid bringing backpacks or large bags to pass through the Naval Academy security checkpoint easily; purses are allowed.
No food or drinks are included, but the guide can suggest nearby cafés where small breaks can be enjoyed. The tour operates Monday through Saturday, from 8:00AM to 8:00PM, giving plenty of options for scheduling.
The 5-star reviews highlight the expertise and charm of guide Michael, whose knowledge and storytelling elevate the experience. Visitors appreciate how he adjusts to group interests, making each tour unique and engaging.
The value of a private, customizable experience in a city as charming as Annapolis makes this tour stand out. It’s especially suited for those who want a personal, in-depth look at the city’s history and scenic waterfront, all within a comfortable two-hour window.
This tour offers a well-rounded exploration of Annapolis’s historic waterfront and institutions, guided by a passionate local expert. The combination of beautiful water views, historic landmarks, and engaging storytelling makes it especially appealing for first-time visitors or history enthusiasts.
While the tour covers a lot in just two hours, it remains relaxed enough to enjoy each stop and take photos. The flexibility and personal approach from Michael ensure that each group’s experience feels tailored and memorable.
For anyone interested in the maritime history, colonial architecture, or early American government, this private walking tour presents a rewarding and informative way to spend a couple of hours in Annapolis.
“Michael was an excellent guide! It was cold and rainy and he was very accommodating to our postponing the walk until a later time. Highly recomme…”
Is this tour suitable for children?
Yes, the tour’s short duration and engaging storytelling make it suitable for families with children, especially given the visual appeal of waterfront and historic sites.
Are tickets required for the stops on this tour?
No, all stops are free of charge, and no tickets are needed to visit the landmarks included.
How physically demanding is the tour?
The tour involves walking but has a relaxed pace. It is accessible for most travelers, though very limited mobility might require additional planning.
Can I customize the tour?
Yes, the guide welcomes requests for customization to focus on particular interests or sites.
What should I bring?
Participants should consider bringing a camera, comfortable walking shoes, and a small bag (purses are allowed, but large backpacks are discouraged for security reasons).
What if it rains?
The tour can be postponed if weather conditions are poor, as the guide is accommodating and reviews praise the guide’s flexibility.
When is the best time to book?
Booking at least 34 days in advance is recommended to secure a spot, especially during peak travel seasons.
What is the cost of the tour?
The private group rate is $235, covering up to 10 participants.
Is parking available nearby?
The tour starts at 25 Market Space, a location near public transportation, making it accessible for travelers arriving by bus or car.
How do I contact the tour provider?
You can reach Michael at +1 410-858-4704 or via email at [email protected] for booking or questions.