In a city steeped in history, Jimbo Williamson, aka The Tie-Dye Tour Guide, stands out as one of Boston’s most colorful characters—literally and figuratively. A longtime tour guide turned entrepreneur, Jimbo has reimagined what it means to explore the city by combining Boston’s revolutionary past with modern cannabis culture. Through his Cannoli & Cannabis Tour, he offers a laid-back, educational, and entertaining experience that celebrates freedom, flavor, and the spirit of the city.
An Interview with Boston’s Tye Dye Tour Guide
How did the idea for The Tie-Dye Tour Guide and your Cannoli & Cannabis Tour come about? What inspired you to blend Boston history, culture, and cannabis into one experience?
I have worked as a tour guide for almost two decades, and initially, it was for other people. I did duck tours, segway tours, and a few other food tours. Eventually, I came up with my first idea, the Pizza, Beer, and Paul Revere Tour! I brought that idea to my current boss at the time, and he said no to it, because it wasn’t “on brand”. So I decided to start on my own… a month before Covid hit.
I paused for a year, then lined up with Airbnb; they let you host experiences for free (although they take a good chunk on the back end), but get you in front of thousands of eyes. That first year was a proof of concept, “Is this gonna work?”….and it totally did! Enough so that I asked myself aloud if I could do another tour of things I love, could I possibly do weed and cannoli!? That has also totally worked!
After that, I opened my own website and branded myself the Tye Dyed Tour Guide. It’s been five years now that I’ve been on my own, and it’s been the best five years of my life! And I owe it all to my guests, because otherwise it’s just me walking around, getting stoned alone and talking to myself…and they frown on that downtown.
Since launching, how has the tour evolved or grown in popularity? Have you noticed a shift in the types of people joining your tours over time?
I have seen steady incremental growth in popularity over five years. I’ve always said it’s like getting the ball rolling: in this instance, I had to first invent the ball, then find the hill. I’m now pushing that ball up the hill, and I can see the top! Once I hit the top of the hill and get it to crest it, it’ll keep rolling on its own! People seem to really love this tour.
My current goal is to get it in front of as many eyes as possible, and articles like this are huge in helping me reach my goal! I get all types, too! Grandmas and gangsters alike!
What’s your favorite part of working with the public and educating them about both cannabis and Boston’s colorful, historic side?
I take my job as a tour guide pretty seriously, despite having a really fun tour. I work as an ambassador to our city and its history. These folks are spending two hours with a wicked local, and more often than not, I’m the only actual interaction with a Bostonian they get – aside from standing in line at Dunkies and listening to Union workers use funny accents to order a coffee and a French crullah!
I take pride in showing them really deep history, but doing it in a way that isn’t boring. I say my goal is to make it like we’re hanging out and smoking with an old friend, in a new city!
In your opinion, what makes Boston such a special or unique city for combining tourism and cannabis culture?
The history of our city is tangible. You can touch the old State House built in 1713, see the balcony where the Declaration of Independence was first read to the streets of Boston (back then the quickest way to get information out was to yell it real loud from a balcony, we didn’t have Twitter…we don’t now either, but you get it), all while standing at the memorial for the lives lost in the Boston Massacre. To be able to do that after having just smoked a joint really hammers home what a bastion of freedom Massachusetts has always been.
You’ve probably met a lot of interesting people on your tours — do any fun or unforgettable stories stand out?
I have had well over 10,000 guests join me over my tenure as a tour guide, but one of my favorites was last year. I went on NPR’s Jim and Margery at the Boston Public Library to promote my tours, and a few weeks later, I had a very interesting two groups. I had a lovely couple from Atlanta, two African American lesbian doctors, as well as 5 grandmas from Brookline. It was such a trip crankin’ a doobie with this group! The older ladies and younger ladies were all laughing and passing joints. It was one of those moments where…these two groups may never have interacted, never mind hung out and cranked a J together!
How do you balance keeping the experience fun and laid-back while also promoting responsible cannabis use and breaking down stigmas for visitors who might be new to the scene?
I take a path with cannabis on this tour where I try to focus more on the fun part than the deeper legislative history of the plant and our city. I mention we were one of the first to go recreational, but I purposely keep it light.
We do smoke outside in a park, which is technically illegal…and I remind them that I fully believe we have to take our moments to be civilly disobedient when we are faced with silly laws, especially about this plant.
What’s next for The Tie-Dye Tour Guide? Any plans to expand into other neighborhoods, introduce new tour themes, or collaborate with other local businesses or creators?
I’m really excited for this next year! So far, I’ve bootstrapped everything myself, from building the tour and route, to selling it to customers through my own website and finding other third-party retailers to do so as well, to learning how to shoot/edit/produce my social media videos I make for each tour.
This summer, I hired a marketing consultant and a new web guy. We built a new site with much better SEO and developed a whole marketing plan, including shooting social media commercials, actually advertising, and measuring Google Analytics. This next season stands to be my best one yet!
I’m focusing on these two tours for now, and continuing to build the relationships inside the best neighborhood in Boston, Little Italy, aka the Old North End. If you’re ever there, I’ll be easy to find….since I’m the most colorful character in town!!
