1 If By Land Walking Tours

Ira was so knowledgeable and entertaining. He knows the city inside and out and had funny snippets interspersed with his narrative.

The tour with Ira was great! He was very informative and had interesting content. It was also nice to have a small group and the headphones were really nice to have with all the road noise and other tour groups that were close by.

Ira was a great tour guide. Very knowledgeable and had interesting stories to share about the city. Customized it to our needs and interests. Highly recommend.

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.

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.

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

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!

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!

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!

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!

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.

Great tour. Informative, entertaining, and interesting. I feel like we got to know Boston really well in a short amount of time. Great tour.

Ira is a great guide with good knowledge of the city. Shared a lot of interesting facts with our group. Highly recommended

Ira was a pleasure. He was very knowledgeable about so much and he emphasized on all the beautiful architectural history Boston had to offer. Which my wife and I loved. Random people who weren't apart of our tour party told us how great his tour is and they were right. I recommend this to anyone and everyone who wants a tour of the beauty and history that Boston has to offer.. I'm originally from Boston and | learned a lot! Thanks again Ira!

Ira was everything you want in a guide: extremely knowledgable, flexible, punctual, responsive, and able to read his audience.

Excellent in detail walking tour that covered all the important sites not to miss in a small group. We enjoyed the architecture intro and neighborhood stories

We loved our walking tour of Boston! Ira was friendly and communicated well before, during and after our tour. We walked at a comfortable pace and covered varied areas. We talked about history, food, real estate, architecture and culture! Ira was very knowledgeable about all. He used an iPad to shore pictures to enhance what we were experiencing first hand. He even helped us find a restaurant for our evening meal. The use of ear pieces made hearing his commentary clear and easy! I highly recommend this tour.

We booked this tour last minute, and am so glad we did! It's a tour that encompasses the city of Boston's history, as opposed to the more common history of the American Revolution. Ira walked us through gardens, parks, and numerous neighborhoods. It was a perfect first day in Boston and gave our family a great introduction to the city. The tour ended near the North End where we had some wonderful Italian food. There is a lot of walking and hills involved, so be prepared. Highly recommend!

We had a great experience with Ira. It was a long and well-planned walk, and Ira kept on telling us all those stories of the buildings on the way.

Ira was a great guide through many interesting areas of Boston. He is very knowledgeable about important historical events, architecture, and current events. I liked that he used headsets as opposed to and obnoxious speaker like many other tour guides you will see in the city. He is also good at giving tips for other things you’d like to see or eat, or help with navigating the subway. I would highly recommend this experience to learn about Boston!

Ira lived in the city for many years and is very knowledgeable about the history of the city. He is very flexible on the schedule and put in a 110% percent even though it was 92 degree out. He uses bluetooth earpieces so everyone (including my 12 and 14 years old) can be fully absorbed in his story telling. I also appreciate the historical photos and maps that he brought along with his iPad. His various restaurant and itinerary recommendations made our Boston experience more enjoyable. I'd recommend his tour to any of my friends visiting Boston.

Ira was so knowledgeable and professional. He arrived to the meeting spot early and was waiting for us. He blends technology (headphones to make hearing him much easier in a loud city environment, and an iPad for photos) and old fashioned know how in a seamless manner. He didn’t walk too fast or too slow, just kept us going at an appropriate pace and took pictures of us for our families. It was a great blend of historical Boston and modern history of the city. We rate it a 10/10. The headphones came in clutch because my father in law wears hearing aids due to extensive hearing loss and he had no trouble hearing Ira thanks to the headphones setup. Don’t hesitate, just send it! Enjoy your vacation in Boston with Ira and rest assured you’re in excellent hands.

Ira is very entertaining and knowledgeable. He knows a lot of things about the city and seems to know half of the population in the area. Very passionate and dedicated guide. Our family of 4 is very glad to have him as our guide.

First class tour. Guide very knowledgeable about Boston and a good storyteller. Also lots of ‘off the script’ interesting info. And only few people on the tour compared with other tours we saw.

I had a fantastic morning on Ira’s walking tour! He was incredibly knowledgeable and passionate about Boston’s history, making the experience both informative and enjoyable. Ira’s storytelling brought the city to life, and he made sure everyone felt included and engaged throughout the tour. I highly recommend it to anyone looking to explore Boston on foot!

Great tour-I’ve done lots of these and this was one of my favorites. Learned a ton and was a good pace. Stopped at fun places and learned of a few I had never heard of before

It’s is an amazing tour guide! His live for Boston and its history is truly astounding. There wasn’t a question he couldn’t answer. The research and care he took to ensure we had a unique experience was impressive. You will not have this kind of experience learning about Boston with a regular tour company. Ira had shared many details that only a true Bostonian with a passion for it’s history could share. Definitely not a scripted tour and no costume required. Worth every penny and then some. Thank you, Ira, for a truly amazing afternoon we won’t soon forget.

Ira is personable, informative, fun, and gives a balanced tour that has something for everyone. I liked his tour so much that I booked it a second time! You won't be disappointed if you book a tour with him.

Had a great walking tour with Ira! Very informative and great way to get introduced to the city. He also had great recommendations for places to eat and drink, several of which we tried. Highly recommend!!

Ira was great! The headphones were awesome and very smart. We had no trouble hearing his historical (and sometimes hysterical 😂) anecdotes and stories. Highly Recommend this tour!!

I couldn’t recommend enough! All the stories and unique places made the best memories. The host had the most attentive and positive energy. Glad I booked this tour as my first activity upon arrival. 10/10.

Wonderful tour. perfectly paced. good historical photos on the iPad that's eye opening. Ira is super thoughtful to make anyone comfortable. highly recommend.

We had a great time with Ira - got 6k steps and covered a lot of ground. Glad we had a reasonable size group of 6-8 and not the 30+ that other groups had. The ear pieces to hear helped a lot so we could always hear Ira without him needing to yell or compete with other tour groups.

My husband and I loved our tour with Ira! It covered many of the quirky history facts around Boston. The tour was even more special since we walked through the finish line of the Boston Marathon during race weekend. Ira was very professional. Highly recommend!

Ira is one of the best story tellers l've had the pleasure to encounter. He was very funny, very informative. He included so many great anecdotes and little tidbits in the tour and his use of the iPad with all the wonderful old photos really made the tour extra special. My family really enjoyed him and the tour—he made us feel welcome and added some personal touches that felt above and beyond. We highly recommend him—it was the best walking tour we've had!

Ira was an amazing guide! He kept the tour very interesting and provided great tips throughout the city! Great time. I can’t believe we covered so much in such a short amount of time.

Ira was a really fun tour guide. We wanted an informative yet fun tour of Boston and Ira ticked all the boxes! We felt comfortable asking questions and he tailored the tour to our interests. Ira knows a wealth of knowledge about Boston and his passion really came through on the tour. Highly recommend for anyone visiting Boston!

Ira was a wealth of knowledge and also incredibly entertaining to listen to! Additionally, I really enjoyed the remote microphone system he used, I could hear him 100% of the tour even though I was not right next to him. This way I could take pictures and catch up to the group at my own pace. Great tour, highly recommend!

Absolutely wonderful tour! Ira was very personable and kind. His knowledge of Boston's history was like no other and the anecdotes he shared along the way were a nice touch. We also appreciated how communicative Ira was. He kept us in the know prior to the tour regarding the meeting time and forecasted weather, which allowed us to plan accordingly. Thanks again, Ira!

I would book this tour again! Ira is so knowledgeable, witty and a really great story teller! It was so helpful to have his iPad to reference images from past to present (and inside locations if you chose to not go in). I'd recommend this tour for all ages - a really great experience!

This is a definite MUST DO! Ira is a wonderful tour guide and showed us fantastic sights and great stories. He was easy to follow and had a microphone and earbud system that made it even easier to ensure we could hear everything clearly despite when the city noises got loud. We learned history, saw beautiful places, and had so much fun. He is a brilliant guide with no gimmicks. I am so happy we found him. Stop searching for anything else and book this tour when you visit Boston! You'll be glad you did!

I had an amazing tour around Boston! The guide was fantastic—he was great at storytelling and made the experience even more enjoyable. As someone whose first language isn’t English, I really appreciated how he explained every detail clearly, which helped me and my friend a lot. I would highly recommend taking this tour—it will make your trip so much more enjoyable!

Ira's passion popped out of his eyes as he talked about Boston , his depth of knowledge and friendliness is next level. He was even kind enough to send me recos after so I have an exceptional experience

Ira was an amazing historian. He was so knowledgeable and personable and made the tour enjoyable for all. Would recommend this tour for anyone visiting boston

One of best city tours I ever had,very knowledgeable guide,he gave us comprehensive historical and architectural perspective. thank you.