FREE! Annapolis Walking Tour

Verified 5-Star Reviews on TripAdvisor  

  • I stopped posting reviews after 2018 because they all say it’s a great tour and I don’t need to keep patting myself on the back.
Reviewed by M1Calico
Jan 11, 2018

 
One of the BEST tours I’ve taken in any city, by any tour guide … and I’ve toured many. Steve knows Annapolis from the history to stories of locals and the issues of the city. He weaves these stories throughout the walk in a way that is amusing and insightful, making the 2+ hours of the tour fly by and leaving one wishing the tour would not end and that he would tell just one more story (even on an icy 30 degree winter day). I got his book “Water Views”, on Amazon, (my brother in law won the book in his contest) and I enjoyed reading his essays. He writes from his heart and his experience, just as he speaks. This is a must-do if you are in Annapolis for even just a day. I will contact him again for a tour on my next visit.

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Reviewed by 789staceys
Jul 13, 2019

 
This is really like a “backstage” tour of Annapolis! The morning my husband and I went, everyone else cancelled so we essentially got a private tour and are so thankful for Steve for not bailing (despite how hot it was!) If you’re looking for a verbatim tour of history with names and dates you’ll never remember and don’t actually care about- go pay $$ somewhere else. Steve will show you around, point out all the places/landmarks in Annapolis, walks you around the town and streets and gives you the inside scoop about all the places (where to get the best food, night life, etc.) he also has an impressive personal resume deep seeded in the politics, history and culture of the area and has so many interesting stories you would never hear from anyone else.
 
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Reviewed by MrandMrsT24
Jun 15, 2019

 
My wife found Steve online and took a chance that he might be available for a tour and we are thrilled that he was! We walked from the waterfront to the entrance of the Naval Academy and through the historic district in a whirlwind that covered nearly three hours. We got history and “in the know” detail of the various goings on in Annapolis. And while we were sitting listening to the tale of one particular building a tour bus rolled by – made us smile. They were getting blah blah blah and we were getting background and dirt. Well worth your time and by the way…Steve does not charge for this experience – tips only. As generous as Steve is with his time, please be generous in return.
 
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Reviewed by Colleen C
Jun 9, 2019

 
We came down to Annapolis for a long weekend and lucky we saw Steve’s tour. We had a great time learned the backstory of Annapolis from a well-rounded native. His tour is a must do, after the tour he points you in the direction of many other things to do and great places to eat.
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Reviewed by jackmartha

Sep 8, 2017

 
If you only have a few hours to learn the past and present history of this beautiful city Steve Carr’s Walking Tour should be your only choice.The time passed by much too quickly and left us wishing for more.Once your tour is completed you will know how to further enjoy your stay in the area and what not to miss and more importantly what to miss.
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Reviewed by tcal2296
Aug 8, 2017

 
Our guide, Steve, made Annapolis come alive before our eyes. My boyfriend felt like we were attending the theater. The man is a consummate performer and his love for his hometown was very compelling. Free! Annapolis Walking Tour is the best deal in town.
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Reviewed by TobeyTyler
Aug 3, 2017

 
We have done walking tours all over the world and I would have to say that the Free! Annapolis Walking Tour was the best one my wife and I have ever taken. Usually these free walking tours are led by a nice young person who refers to a script. The Annapolis tour was guided by a retired guy who has lived in Annapolis for over sixty years. He had some really funny and interesting stories. And he had a contest at the end where he gave away one of his books. We were blown away by the whole experience.
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Reviewed by Ron K
Aug 2, 2017

 
I am a native Annapolitan and on a recent whim decided to act like a tourist and check out Free! Annapolis Walking Tour. Oh Boy! I am really glad I did. There is a quote from one of my favorite bands that comes to mind, “Once in a while you get shown the light in the strangest of places when you look at it right” and my guide, Steve Carr, shined a light on Annapolis like no other. Not only are his stories incredibly amusing but very insightful and I am proud to say I was the winner. So not only is Steve a tour guide but he has published five books including a book called “Water Views” about the Chesapeake Bay. It is a beautiful coffee table book with photos of the Bay and because I was the first person who correctly answered his end of tour trivia question (make it more difficult Steve!) I walked away with a signed copy of his book. I love the concept of this tour and highly recommend it to all!
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Reviewed by John R
Jul 21, 2017

 
The Free! Annapolis Walking Tour was the best tour I have ever taken. I have lived here for a few years, but decided to try this FREE tour out with some co-workers who were visiting from out of town and our guide, Steve Carr, knew EVERYTHING about the old city and he was incredibly entertaining. We especially liked the many different places he took us that most tourists never see. And his stories were both informative and hilarious. You can’t beat the price, and the walk was easy and by far the best thing we did during their stay in Annapolis. If you do one thing while visiting Annapolis, do the FREE! Annapolis Walking Tour. You will definitely be glad you did.
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Reviewed by ANAfromSF
Jul 15, 2017

 
This was one of the best walking tours we have ever taken. Our guide, Steve, has lived in Annapolis all his life and he had the stories to prove it. He took us to all the Colonial attractions but he didn’t pile on a lot of boring historical facts. What we got instead, were often funny tales about a town that Steve clearly knows quite well, but also loves dearly. The FREE! Annapolis Walking Tour is a unique experience that you do not want to miss if you are visiting Annapolis. And, you can’t beat the price.
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Reviewed by svetlanadaleo
Jul 14, 2017

 
Annapolis Walking Tour was the best deal in town. We learned about the history. But our guide Steve told us some really funny stories that we would have probably never heard before. It was an incredible experience!
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wendywein wrote a review Aug 2020
7 contributions2 helpful votes
 
 
Steve was quite knowledgeable, & as we were the only two on the tour, geared it to our interests. His stories and discussion of Annapolis architectural sites and historical preservation policies was outstanding. He explained the transition from a slave state within the union during the Civil War and segregation in the 1950s to the situation today.
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Reviewed by Bob W
Apr 3, 2019

 
Steve, our tour guide, is very smart, very funny, and very opinionated. He is also very knowledgeable about the history, the politics, and the social scene in Annapolis. All five of the adults in our group enjoyed the tour, and we learned (and laughed) a lot.
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Reviewed by 5562_0520
Mar 27, 2019

 
Great tour . Very knowledgeable about the area . Tour is for adults only as Steve’s language can be “colorful ” at times. Good stories about local politics . We had a great time . Thanks Steve !
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Reviewed by Ken J
Mar 23, 2019

 
Great tour by a unique, knowledgeable, fun native Annapolitan who really brings this town to life. Loved his stories.
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Reviewed by hikingtheglobe
Mar 12, 2019

 
My friend and I thoroughly enjoyed Steve’s insight into Annapolis. He has his own entertaining way of combining Annapolis’ history, the workings of the town’s government and the town’s social climate. Being native to Annapolis, and having been a member of its inner workings, Steve has a handle on it all – the good and the not so. He also is great at directing visitors to their interests whether dining, sightseeing, entertainment, etc. all peppered with Steve’s unique interpretation. This was well spent time in this charming, historic, first capital of the USA.
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Reviewed by Stephen M
Apr 22, 2019

 
A fantastic tour. Takes a little over 2 hours and well worth your time. You will learn things about Annapolis and its people that you will not learn anywhere else. In a short time, we learned about some of the architecture, the history, the politics and the issues facing Annapolis – both historical and at the present. Highly recommend Steve’s tour.
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Reviewed by expres981
Dec 8, 2018

 
My husband and I enjoyed our time with Steve. He gave us personal attention with behind the scene info about Annapolis. Steve’s tour is not for the faint of heart yet very entertaining and informative!
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Reviewed by Neil C
Dec 8, 2018

 
Steve’s tour provides a great introduction to Annapolis in a fun, unscripted manner. He has a great personality and a lot of insider knowledge of Annapolis and its history. He really worked with us to develop a game plan for the rest of our visit. Highly recommend.
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Reviewed by markfern84
Nov 11, 2018

 
Hi Steve Thanks You Steve!!! You are a TOP GUN at what you do (Kudos)!!! Really enjoyed the tour & Your Personality as a World Class Story Teller! It was the Highlight of my Trip to Annapolis! With Respect & Appreciation!!!
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Reviewed by Trail29768613528
Nov 4, 2018

 
Steve is friendly local guide born and raised in Annapolis. He knows stories related to times he was growing up as well as times when he was running political campaigns. Absolutely would do it again! This walking tour was just right! It helped our family to appreciate beautiful Annapolis even more.
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Reviewed by Bill L
Sep 26, 2018

 
Steve’s stories of his unique personal local history is not to be missed. His connection to local political leaders and life long residence provides insights you will not get from the costumed actors from competing tours. if you want to informed of local places and history this tour is not to be missed. Added recommendations on the best places to enjoy locally is a bonus.
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Reviewed by Steve R
Aug 18, 2018

 
This walking tour is a great start to anyone visiting Annapolis for the first time. The tour takes two hours plus. Steve knows more about the City and happenings than the run of the mill tour guides. Make sure you email or call for a set day and time. Steve highlights the buildings and historic sights you surely will want to return too. Don’t forget to ask for some restaurant recommendations.
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Reviewed by Laurie S
Aug 10, 2018

 
Steve was fantastic!! This was a perfect start to a getaway weekend for my wife and I. Steve was engaging, extremely knowledgeable and best of all he made the tour fun. Would recommend this to anyone looking to visit Annapolis. Gave great advice for things to do while we are here.
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Reviewed by TheChief37
Jul 11, 2018

 
Steve Carr is an engaging guide. Born and raised in Annapolis, Steve knows his town. Great sense of humor and good advise for good places to eat and drink!
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Reviewed by Pat H
Jul 3, 2018

 
Our tour with Steve was amazing. His story and the history of Annapolis are intertwined and fascinating. We were in Annapolis for an extended Father’s Day weekend with our two teenage boys in tow. Although the boys gave the impression that they were too hot to take much interest, they accidentally revealed over dinner that they had been listening more carefully than they let on and had not only enjoyed the tour but had learned a lot. Time with Steve is time well spent!
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Reviewed by Catherine S
Jun 27, 2018

 
Steve was absolutely great! He took the time to tell fascinating stories that most other guides would never have known or even shared. We also loved learning some of the lesser known facts about the area. Having a background in politics, Steve knew many of the inside why’s and how’s of this areas unique growth and ultimate development. Take this tour! You will greatly appreciate where you are the next day. Also he made great recommendations of things to see and do on our own.
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Reviewed by jillaltman72
Jun 18, 2018

 
Stephen gave our family a tour on a hot summer day. Keeping 2 teenagers interested enough that they weren’t complaining says a lot. After our walk we couldn’t decide if we found Annapolis or Stephen himself more interesting. Great way to see the town!
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Reviewed by VincentC680
May 12, 2018

 
My wife and I are so happy to have taken Steve’s tour to begin our visit to Annapolis. His inside information and suggestions on how to visit this area are invaluable. Everything that was said by other reviewers is right on. His tour is a must when visiting Annapolis.
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Reviewed by richlazor22
Apr 30, 2018

 
If you are spending a few days in Annapolis; you must absolutely do a walking tour with Steve. First off; the weather at the start of the tour was iffy to say the least with rain ending right before scheduled start of tour. Steve was there right on time. Great local knowledge with plenty of Steve’s personal stories from his time in Annapolis so you don’t get just the random tourist facts. Steve spent more than the scheduled 2 hours with us and it was all enjoyable. Great recommendations on what to see at Naval Academy; what sights were must sees an where to eat and drink while in town. All in all – time and money well spent. Thanks much Steve wife and i enjoyed it all.
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Reviewed by Patrick C
Apr 15, 2018

 
Steve hosts a very knowledgeable and entertaining walking tour of Annapolis, he is an Annapolis native, he attended the Naval Academy and was involved in local government. Steve is a fountain of local information! If you have 2 days in Annapolis I would recommend taking the tour the first day and then visiting the places that interest you in more detail the second day. We really appreciated Steve’s insights to Annapolis from the monuments to the historical sights to the restaurants and bars.
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Reviewed by intikab h
Apr 10, 2018

 
My family and I arrived in Annapolis from a week-long vacation in Jamestown and Yorktown. We were tired and I didn’t have any energy to or time to plan a day of history, sightseeing, and discovering the city. That is when I did a search of free tours and found Steve. I called him to see if he had a tour and he was accommodating and put aside his his writing and took us on an informative and entertaining tour. Steve even gave my teenager son a free copy of one of his books.
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Reviewed by Sardo4
Apr 8, 2018

 
We took Steve Carr’s walking tour on Easter weekend. It was the highlight of our visit. Steve’s stories are fun and informative. Highly recommended!!
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Reviewed by crazybubna
Jan 27, 2018

 
If you are in Annapolis for a day or longer, this tour is highly recommended. Steve has a lot of knowledge about the city and worked in public office here too so he has the inside dirt about everything in and around the city. We had an awesome time
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Reviewed by Marcia B
Jan 15, 2018

 
This was the highlight of our Annapolis trip. Steve was so interesting and informative…much more than just dates and names…he KNOWS the city and it’s goods and bads. It was so cold when we did this last week (I’m from SC) but the time flew by and Steve gave us a nice break to warm up at a local bookstore. I would HIGHLY recommend this tour!!
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Reviewed by windsurfer_2003
Dec 10, 2017

 
My sister and brother-in-law were up from Wilmington, NC, and we thought they would enjoy seeing Annapolis and booked the tour. We live in Alexandria, VA and visit Annapolis two or three times a year. We should have done this tour long ago. Steve is a native of Annapolis and really can get you underneath the tourist veneer. He has great recommendations for dining and, having been part of city government for years, he is knowledgeable of recent history and current issues in Annapolis. It adds to the tour that he is acquainted with some of the residents in homes along the tour. Steve pointed out three Georgian homes for architectural comparison. Among other things, we learned about St John’s College, the Naval Academy, the Maryland State House. We also got to see a Tiffany window. We will get more out of our future visits, thanks to Steve.
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Reviewed by Eddie T
Nov 5, 2017

 
My family and I had a blast on this free walking tour with Steve. Steve is enthusiastic, knowledgeable, and provides a unique perspective on Annapolis. I’ve lived in Annapolis area for 20+ years and was surprised by how much I learned. What makes his walking tour unique is his background of working for the city for many years, attending the Naval Academy, and living in the area for dozens of years. Steve is a story teller and he’s able to share his experience of living and working in Annapolis through his fascinating narratives. You won’t be bored with event dates and dry history. He is extremely personable, funny, energetic. At the end of tour, there was a fun trivia question and as a prize, he gave us an interesting illustrated book about Annapolis that he wrote. All four of us enjoyed the tour and thought it was amazing! We highly recommend it to tourists and locals; families, couples, and solo; and to anyone who is interested in Annapolis!
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Reviewed by rarussel
Oct 24, 2017

 
My wife and I were lucky enough to be the only 2 on the tour with Steve on a bright sunny autumn day. His life experiences and family connection to many of the historic sites we toured, made for a very unique and enjoyable tour of Annapolis. His honest slant on the history and politics of the area and his amiable delivery holds your attention throughout. We highly recommend Steve’s tour.
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Reviewed by iworktovaca
Oct 16, 2017

 
My husband and I did Steve’s walking tour while we were visiting college friends in the area. It was our first time in Annapolis and we enjoyed hearing and seeing the city from a long time locals perspective. He gave us one of his books at the end of the tour, which will be a nice memory of our trip.
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Reviewed by BobMtSnow
Oct 14, 2017

 
We thoroughly enjoyed our walking tour. Steve is funny and very informative about the behind the scenes history of Annapolis and the Naval Academy. An added bonus was restaurant recommendations. Thanks Steve!
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Reviewed by Starviagera
Sep 14, 2017
 
 
Free walking tours always have interesting guides. We had a very informative tour and would recommend it. People are always concerned about how much of a tip to give. We checked out what the regular tours cost and go from there.
 
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Reviewed by Federico E Cura 
Aug 6, 2020
Arlington, Virginia1 
 
No better way to visit Annapolis (historic district) than from the perspective of someone who knows it well, knows the locals, and who lives there. Steve knows the businesses there and has intimate knowledge of the people and the history. He has the ability to make otherwise dry material come alive in a fascinating way. Great tips on restaurants too!
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