Tours/Annapolis/Annapolis Historic Walking Tour: Harbor and Colonial Downtown
Viator · Private tour

Annapolis Historic Walking Tour: Harbor and Colonial Downtown

5.0(46)Annapolis1 hour
VIATOR5.0(26)TRIPADVISOR5.0(20)

Description

Take a pleasant walking tour through the beautiful historic center of Annapolis, including the picturesque harbor and US Naval Academy. 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!

Tour Options

Annapolis Historic Walking Tour: Harbor and Colonial Downtown

Itinerary

10 min

See the waterfront of Annapolis, the Harbor, Severn River, and the Chesapeake Bay, and hear the story of Annapolis's beginning.

20 min

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.

15 min

Admire the neoclassical architecture, maritime-themed stained glass, and Crypt of John Paul Jones at the Naval Academy Chapel, built in 1908.

20 min

Admire the facade and learn the story of one of Annapolis's most beautiful homes, dating back to the "Golden Age" of late colonial Annapolis.

10 min

Visit the third-oldest institute of higher learning in the United States, dating back to 1696: St. John's College. Learn about its unique Great Books liberal education, its colonial architecture, and the annual "Annapolis Cup"!

30 min

Experience the oldest state capital in continuous legislative use, dating back to 1772! Learn why Annapolis is the first peace-time capital of the United States, and see the room where George Washington famously resigned his commission as Commander-in-Chief of the Continental Army.

Highlights

No tickets are required for the stops on our tour.
Tour guide is happy to take photographs of your group at scenic locations.

What's included

Included
No tickets are required for the stops on our tour.
Tour guide is happy to take photographs of your group at scenic locations.
Not included
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.

Traveller Ratings

5.0
46 reviews
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46
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2
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Important Information

  • 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

Reviews(46)

L
lktowens
July 11, 2026
Great Historic Annapolis Tour

Absolutely fantastic & informative tour. Highly recommend!

B
Barbara_L
July 11, 2026
Annapolis Tour

Our tour guide, Michael, was extremely knowledgeable and answered all our questions. The private tour for our group of 4 adults was worth the money.

S
Sheila A
June 12, 2026
Great trip! Excellent tour guide

⭐⭐⭐⭐⭐ Had a great time touring Annapolis with Michael! He was friendly, knowledgeable, and made the history of the city really interesting without it ever feeling like a lecture. You can tell he loves what he does and genuinely enjoys sharing Annapolis with visitors. We learned a lot, saw some great spots we would have missed on our own, and had a lot of fun along the way. If you're visiting Annapolis, I highly recommend taking a tour with Michael. It was time well spent!

S
scottlX1470XY
June 3, 2026
A Perfect Gift for the Dad in Your Life

Michael is an excellent tour guide. He’s knowledgeable and explains things very well. I got this walking tour as a present for my dad, and he LOVED it. We all had a great time. My dad uses a wheelchair, and he had no problem getting around. This tour was worth every penny, and I’d definitely book again with Michael in the future.

R
R6691BDmollym
April 26, 2026
Excellent

Michael was easy to work with especially when weather could have changed the experience.

L
Lois_B
April 14, 2026
Lovely walking tour...

Lovely 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.

1
143luckyc
February 28, 2026
Great intro to Annapolis

Michael 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.

S
Sabrina_B
February 15, 2026
Best Day!

Michael, 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.

M
Mark_A
November 12, 2025
Smart and nice!

The 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.

J
Jeffrey_A
November 10, 2025
An Amazing Town with Amazing History

Unfortunately 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.

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