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Boston Historical Photo Tour: See the City Then and Now
5.0
93 Ratings
Boston
We will be walking all around the great city of Boston. Along the way, as you look at the city that stands today, I will show you historical photos of the exact spots you are standing on. Be prepared to experience Boston the way you never could imagine.
We will be walking all around the great city of Boston. Along the way, as you look at the city that stands today, I will show you historical photos of the exact spots you are standing on. Be prepared to experience Boston the way you never could imagine.
Duration:
2 hours, 30 minutes
Cancellation:
24 hours
Highlights
- 1 If by Land Walking Tours - Meeting spot
- 1 If by Land Walking Tours - Meeting spot

What's Included
- Headsets to hear the guide clearly
- Driver/guide
- Headsets to hear the guide clearly
- Driver/guide
What's Not Included
- Drinks
- Food and drinks
- Gratuities
- Drinks
- Food and drinks
- Gratuities
Additional Information
- Children must be accompanied by an adult
- Children must be accompanied by an adult
Location
Back Bay
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
5.0
(93 Ratings)
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232yeimig
Sep 28, 2025
Best Tour in Boston! - Ira was an absolutely amazing tour guide in Boston! From start to finish, he brought incredible energy and shared an impressive amount of knowledge tailored specifically to us. Knowing we were considering moving to the city, he customized the tour, offering insights on neighborhoods, real estate, food spots, and local stories that made the experience personal and unforgettable.
He even went above and beyond—taking photos of us at landmarks, giving us free chocolate outside the Lindt store (the staff came out just for us because Ira is so well-known), and sending us home with a take-home poster as a souvenir. Every moment was fun, informative, and thoughtful.
If you want a tour that’s lively, educational, and full of insider tips, Ira is your guy. Highly recommend!
Review provided by Tripadvisor
Julianb836
Sep 24, 2025
Ira is amazing - Ira was incredibly knowledgeable. This was one of the best most engaging walking tours I’ve taken in a while. Headsets made hearing him super easy no matter where we were.
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O1284muelisaz
Sep 5, 2025
walk through Boston's history and the city it is today - I had a great experience. Ira walked me through Boston's history and its historic neighborhoods. He showed then and now pictures which helped me get a better understanding of historic events and places. Along the way Ira told interesting fun facts. Through his comments I developed a whole new view on the Boston's architecture. Also, he gave me ideas on how to spend the rest of my stay and tips on how to get around in the city.
Review provided by Tripadvisor
Tracir534
Aug 26, 2025
Awesome Tour and Affordably Priced - Ira was awesome, super knowledge. The tour was incredible value for a low price and I'd recommend anyone new to Boston do this early on to get recommendations for things to do for the rest of their stay
Review provided by Tripadvisor
Tracysb5692wk
Aug 26, 2025
Excellent Tour! - Ira was a great tour guide and extremely knowledgeable. Our tour was a small group of 3 people which made navigating the city very easy. I would definitely recommend this tour to anyone looking to get to know Boston!
Review provided by Tripadvisor
Sealodgeg9
Aug 25, 2025
The best Boston Tour Guide! - Ira is a superb guide…no need to look for anyone else. We have done many guided tours and his was the best experience. Thank you, Ira!
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Lindalw3502px
Aug 25, 2025
Amazing tour with great storyteller! - Take this tour! Ira is a great tourguide and instead of taking the standard freedom trail, he takes you through other neighborhoods of Boston. You get a great view of the town with lots of information on current and historic Boston. Using ipad to show how the past looked like, really nice. He uses headset, which works great even for small group. In transit, you can still folllow his valuable info. Ira ensures that you also get great (group) pictures of Boston highlights. And remember: when you see a beautiful building, always look up!
Review provided by Tripadvisor
Kristink933
Aug 25, 2025
Family tour of Boston with Ira was great! - Our family, new to Boston, went on a great tour with Ira! He was flexible about our logistics, met us right where he said, and the group had a great time. Ira is extremely knowledgeable and fun and everyone, kid to adult, enjoyed themselves. Highly recommend, its a great way to see the top hits of Boston and get a lay of the land in a few hours!
Review provided by Tripadvisor
Wanderer320396
Aug 25, 2025
Must Do In Boston!!! - Ira was a great guide that was not the typical "kitschy" costumed Freedom Trail tours all over the city. Not to knock those we've but been there..done that, and we thought something different was in store for our family. Ira is a historian, and is so knowledgeable about the history, customs, architecture, and art of Boston. It was a perfect amount of info and the walk around was perfectly paced. He also gave us many recommendations of what we could do while in Boston! Thank you Ira! We highly recommend this tour.
Review provided by Tripadvisor
G4159rtkevinj
Aug 25, 2025
Great tour. This is the best way to start your visit to Boston. - Great tour. Informative, entertaining, and interesting. I feel like we got to know Boston really well in a short amount of time. Great tour.
Review provided by Tripadvisor