The Tye Dyed Tour Guide’s Boston Pizza & Weed Outings

“Take in some sights, check out some history, find a nice place on the harbor to … hang out, and then grab ourselves a cannoli from my favorite hidden-gem bakery.”

We don’t employ this cliche often, but really, Jimbo Williamson isn’t your typical tour guide. Especially in Boston, where many of the working pros in that biz wear bronze-buckle shoes and lace jabots.

As for Jimbo’s getup, he’s known as the Tye Dyed Tourguide (yes, spelled like that), so you figure it out. We asked about the origins of his walking persona and his current ongoing offerings, which we attest are as appropriate for locals as they are for out-of-towners.

Tell us a little bit about the Tye Dyed Tourguide. What are some of the experiences you have led in the past?

Well, I’m Jimbo and I’m the Tye Dyed Tourguide. I’m proud to call myself one of the best tour guides in Boston. I’ve worked for a decade for other tour groups—I’ve had nearly 10,000 [tourists] join me over the years, from other pizza tours to Segway tours—and decided over COVID to start my own little tour. I made an internal pact to stay as true to myself as I could, and to only give tours about things I myself love. I promised I’d make this as fun for me as it is for my guests.

As much as people come on my tour for the chance to eat pizza and drink beer, or smoke weed and eat pastries, I have found that people come because they don’t want some old, stodgy dude in tights giving them the brick-by-brick tour of the city. They want a young, goofy local to crack some jokes, bust some balls, and show them the real Boston as only a ball-busting, goofy local can do.

All jokes aside, I take my role as an ambassador to this city really seriously. Oftentimes I’m one of the few people that folks who travel here get to have a real interaction with. It’s usually a couple minutes with a waiter here and there, maybe chatting up the concierge. We get to shoot the shit and walk around for two hours. It’s such a unique scenario where I can be the one to help set the tone for their trip, and show them we’re not all a bunch of massholes.

It seems like tours in general are a great safe pandemic activity. Is that how it’s generally seen? And what safety measures do you have in place? 

Walking tours are a great pandemic activity, in that we’re spending time outdoors and unencumbered by masks (as directed by the state mandates), though we do still wear masks while walking to grab ourselves a beer and a slice of pizza. That said, it’s nice to be able to be outside with your friends and family for a guided activity, as either a tourist or a local.

So, first, you told us about your Boston pizza tour. While I know it may be like putting the cart before the horse, please tell us about the inspiration for the pizza tour before we get to the weed part.

I run the Pizza, Beer, and Paul Revere Tour in the North End. I worked for another amazing pizza tour for a few years, and literally one day had the idea for mine—the rhyme just hit me. I offered the idea to my boss at the time, and he politely shot it down. So, I decided to start off on my own … in 2020. But really, the inspiration comes as a part of my drive to show people the locals’ perspective on our city, to drop the schtick that some guides have and give these folks the experience of walking around with an old friend, which, of course, is the best way to see any city.

I’m bringing people to a pizza spot I’ve been going to since I was a kid with my dad that I used to travel a hour each way to come get. We grab a beer at my favorite little bar in the city, nestled among a strip of tourist traps. We get to see the parts of Boston that date back to pre-Revolutionary times. You forget about that history, sometimes, but people from say, Iowa, are absolutely floored when they’re standing in front of Paul Revere’s house which was built in the 1680s.

What are some of your favorite stops on the pizza tour, and what have your clients really been enjoying? 

While I love the bar and pizza shops we go into, and they’re the top billing, my tour is really about the nooks and crannies that the North End has to offer and others tours ignore. Copp’s Hill Burying Ground has my favorite bullet-riddled tombstone. Yes, I have enough tombstones I like that I can call one my favorite, and no, I don’t think that’s weird at all. There’s a back alley bakery you’d walk right by, and of course Polcari’s Coffee. The owner, Bobby, is such a classic North End guy: kind, gregarious, talkative, and interested in every person I bring through the door. People love walking in that store, it’s like walking into the past, and people really enjoy that moment of connecting with all those lives lived in this old little neighborhood. It’s really true that once in a while, you get shown the light in the strangest of places if you look at it right!

How many slices can a person possibly eat in an afternoon? What’s the current record? We may have an editor or two who wants to challenge it. 

We provide two slices of pizza, per person, on the pizza tour, though we used to do three slices. At my busiest, I was eating nine slices of pizza a day, six days a week—in the hot sun. I’ll gladly accept a challenger who can eat upwards of 50 slices of pizza a week.

Now, what’s the BoSTONER Tour all about? Besides being a clever pun of sorts? 

I ran the [Pizza, Beer, and Paul Revere Tour] for a year after starting out on my own, and have always wanted to do a cannabis-themed tour. When I went all in on the idea of being the Tye Dyed Tourguide, I decided to take that name and really run with it, to make it a brand. Seemed a great opportunity to tie the room together, and offer Boston’s only walking canna tour.

So, we meet up at a dispensary, they can purchase whatever it is they so desire, and afterwards we go for a walk. Take in some sights, check out some history, find a nice place on the harbor to … hang out, and then grab ourselves a cannoli from my favorite hidden-gem bakery. I wanted to provide a safe, smart, fulfilling opportunity for our friends who come to Boston from places where a tour like this just isn’t possible.

What do people need to bring with them for one of these adventures? 

People need only bring comfy shoes, a sense of humor, and their appetite.

What are people most interested in? Besides getting high of course. 

Flat out, people want to hang with a Bostonian, and to see how and where we live. They want to hear some funny accents, see us bust the balls of fans from opposing sports teams, and grab a beer at a divey bar. You’d be surprised at how few are familiar with the rich history that lives on every street in this city … the looks on their faces when I tell them we’re standing in an alleyway that has been there since the middle 1700s is priceless. People want to feel like a local, not a tourist, and on my tour they walk away with a sense that they saw a real slice of life here and can move confidently through our city like they’ve been here before.

What would you have said 10 years ago if we looked into your future and told you that you were going to be working in the cannabis tourism industry in Boston?

If you told me that people would be paying me to hang out and smoke weed with them and show them the city, I would have laughed and told you to roll another. That said, I’m really proud that I could set a goal and reach it. I just never for a second as a young smoker thought I’d be a professional in the cannaworld, but I’m glad to be one of the fuzzy faces of this burgeoning new industry.

And I do owe a bit of thank you to a dear friend, Elmo. He was an ardent proponent of cannabis, and after his untimely passing I decided to try to carry on his torch through this tour, and also another canna biz that I’m certain he would have loved,

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