Private Tour
Annapolis Historic Walking Tour: Harbor and Colonial Downtown
Overview
Available languages
2 hours
Mobile ticket
IMPORTANT UPDATE (3/11/26): The Naval Academy is not currently letting visitors on the Yard for security reasons. Tours currently will focus on the Harbor and colonial downtown.
Take a pleasant walking tour through the beautiful historic center of Annapolis, including the picturesque harbor. We'll see the Georgian mansions, the iconic Maryland State House, and much more as you learn the fascinating story of the town.
We'll see where the Treaty of Paris was signed (bringing to a conclusion the Revolutionary War) and where General Washington resigned as general, thus becoming the "greatest man in the world" and the "American Cincinnatus. " We'll explore the campuses of two institutes of learning that have shaped American culture. We'll walk along the city dock, harbor, and see the view to the Chesapeake Bay and wider world.
I'll also share personal and family stories along the way, to add a personal dimension to the tour. I welcome all questions and special interests for our tour!
Additional Info
Wheelchair accessible
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Transportation options are wheelchair accessible
Suitable for all physical fitness levels
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What To Expect
Ego Alley
See the waterfront of Annapolis, the Harbor, Severn River, and the Chesapeake Bay, and hear the story of Annapolis's beginning.
U.S. Naval Academy
Experience the beauty and dignity of the United States Naval Academy, a 4-year university that trains future officers of the U. S. Navy and Marine Corps. IMPORTANT: visitors over 18 years old must show a REAL ID or US Passport to pass through security at the Academy.
What‘s Included
No tickets are required for the stops on our tour.
Tour guide is happy to take photographs of your group at scenic locations.
To pass through Naval Academy security checkpoint, do not bring backpacks or large bags. Purses OK.
No food, drinks, or desserts are included in the fee. But happy to pause at cafés along the way.
Options
Annapolis Historic Walking Tour: Harbor and Colonial Downtown
Reviews
41 reviews
Total reviews and rating from Viator & Tripadvisor
Lovely walking tour...
Lois B,Apr 14, 2026
- Review from Viator
5.00Lovely walking tour through Annapolis with Michael. We stopped by the gate to the Naval Academy, the Maryland State House, and St John’s College, to name a few places, and admired Georgian and Federalist architecture in the city. Discovered Old Fox Books with a wonderful coffee shop along the way. Everyone in our group said they would take the same tour again.
Great intro to Annapolis
143luckyc,Feb 28, 2026
- Review from Tripadvisor
5.00Michael was a great guide, and the tour was a perfect way to start our day in Annapolis. Michael provided a good backdrop for us to use as we explored Annapolis the rest of the day on our own. He was proactive in his communication prior to the tour and provided some great recommendations for us to explore on our own after the tour.
Best Day!
Sabrina B,Feb 15, 2026
- Review from Viator
5.00Michael, our tour guide, was such a joy! He led us on a fascinating adventure through Annapolis’s deep historical story. As we strolled through the Naval Academy campus, Maryland State House, St. John’s College, and Main Street, Michael shared fascinating stories about Annapolis’s interesting history, its brilliant founders, and the Navy’s amazing past. His tour was a fantastic way to get to know this amazing town.
Smart and nice!
Mark A,Nov 12, 2025
- Review from Viator
5.00The tour is flexible, a decent amount of walking, and is inside and outside. Michael was very well versed and willing to spend more or less time at different locations.
An Amazing Town with Amazing History
Jeffrey A,Nov 10, 2025
- Review from Viator
5.00Unfortunately we did not bring Real IDs or our passports even though it was clearly communicated that we should have, just wanted to put that here to let others know. However, even though we couldn't tour the Navel Academy, Michael still gave us a great overview from a distance. Since my wife and I are history buffs in general, Michael pivoted his tour to focus more on the overall history of Annapolis and other areas of interest. As we were talking he took note of the fact that we admire Washington and took us to the location where the Treaty of Paris was signed and also the written speech Washington gave when he resigned as General. Overall it was a really interesting tour and Michael did an amazing job.
Michael was very...
Mark S,Nov 3, 2025
- Review from Viator
5.00Michael was very knowledgeable and even tracked down a couple of requests we had. He was one of the best guides we have ever encountered!
Annapolis Tour by Michael
Q7841VKjamesw,Oct 27, 2025
- Review from Tripadvisor
5.00My wife and I booked a private walking tour with Michael and it was the highlight of our Annapolis trip. The glowing reviews are spot on! His tour of the Naval Academy and historic downtown was a perfect blend of history, quirky facts, and fun. Michael is an exceptional guide, and we highly recommend him to anyone visiting Annapolis for the first time.
Annapolis is a beautiful,...
Robin B,Oct 26, 2025
- Review from Viator
5.00Annapolis is a beautiful, quaint city with a rich history. Our guide, Michael, was so gracious and knowledgeable. We learned about the history of so many wonderful landmarks in Annapolis and had an impressive view of the Naval Academy on Homecoming game day. Highly recommend!!
Walking Annapolis with Michael
William R,Sep 17, 2025
- Review from Viator
5.00Circumstances beyond our control prevented us from touring the Naval Academy but Michael shifted easily to a wonderful tour of the charming city, covering history, architecture, culture, famous homes and people. Great pace, great information!
Family gathering in Annapolis
JEFFEREY Y,Aug 31, 2025
- Review from Viator
5.00Michael was a great tour guide. Very knowledgeable, and adjusted the tour to events ( midshipmen Parade, etc) and to our specific requests
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