1 If By Land Walking Tours

Ira is a very talented and compelling guide who takes you to places of interest and helps you learn more about what was there before and the intricacies of what is there now. He encourages more thought and exploration of buildings and landmarks beyond the surface level and does it with grace and humor. I got a look into a city I’ve known a lot about for decades and learned a lot of new stuff that I am grateful for. Despite the fact that we did it on a hot day, the full length of the tour (maybe it was longer than normal because I kept picking his brain about things) it flew by. He takes good care of you and is able to shift the focus to/from subjects flawlessly. It’s a very unique way to see the finer details of Boston’s neighborhood while learning more about its history beyond what you may get from a typical tour. And he has good recommendations for places to eat and things to do outside the tour route. Thank you!

This walking tour is-a-must! Ira is enthusiastic, prepared and thoughtful. His variety of knowledge around architecture, history and current events makes every statement within the tour feel like you could easily win Boston Jeopardy.

Ira was amazing!! Very knowledgeable about every part of the city. Highly recommend doing this tour. Good for small group or large.

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!

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.