Every good traveler knows that if you want to find the best restaurants and dispensaries, ask a local. And if you’re spending time in Boston’s North End, Jimbo Williamson is the man you’re looking for. Jimbo — aka the Tye Dyed Tour Guide — leads the boSTONER Cannabis & Cannoli walking tour, a deliciously unique two(ish)-hour experience that artfully combines history, food, and marijuana.
“My tour is like hanging out with an old friend in a new city,” Jimbo says. “I get to be my authentic self, and people see that. Plus, everyone wants to get high and do cool shit.”
The Experience
The tour begins at Apex Noire Dispensary, a Black-owned and -operated, bi-level dispensary that offers a menu packed with smokables, edibles, topicals, and more. To kick things off right, each Tye Dyed Tour Guide participant pays just $1 for any one item marked $50 or less. “Personally, I like fruity sativas for the tour, but even if you don’t partake, it’s still a ton of fun,” he says. From there, the group departs for an educational, entertaining, and enlightening walk through one of the most unique neighborhoods in the United States.
“The North End is full of so much history — history about the city of Boston and about the nation,” says Jimbo. “We don’t tear stuff down and put up a plaque here. We keep history alive.”
In addition to well-known monuments and landmarks, the tour includes stops at less-trafficked spots like a cemetery dating back to the 1650s and a 200-year-old alleyway. The group takes a breather in the shade at Copp’s Hill Terrace, a beautiful place to smoke a J. Popular with locals, this tree-laden green space overlooks Boston Harbor and offers Instagram-worthy views of the U.S.S. Constitution and Bunker Hill Monument.
On the food and beverage front, Jimbo has curated a route filled with ricotta and freshly roasted coffee. Each stop gives a sense of the neighborhood’s unique and storied heritage. “We go to places I believe in and have been going to for a very long time,” he says. For cannoli, the group files into Bova’s Bakery, the oldest Bakery in Boston, which operates 24 hours a day, seven days a week. Coffee fans and cooks on the tour especially love Polcari’s, an epicurean eden that has been selling freshly ground spices and coffee made from locally roasted beans since 1934.
Who Is the Tye Dyed Tour Guide?
Jimbo Williamson is a man of many trades, including Boston Lyric Opera truck driver, bar bouncer, reggae band tour manager, and substitute elementary school teacher. But around the North End, he’s best known as the Tye Dyed Tour Guide.
Originally from Plymouth, MA, Jimbo’s hospitality career began with a job accosting approaching tourists on the street to buy tickets for Boston Duck Tours. From there, he segued to a company that ran Segway tours, where customers voted him #1 tour guide two years in a row. When a coworker opened Boston Pizza Tours a little over a decade ago, he handpicked Jimbo to lead them.
Ever the entrepreneur, it was only a matter of time before Jimbo started a business of his own. He launched the Pizza, Beer & Paul Revere tour, a walking experience through the North End focusing on pizza and Revolutionary War history, in 2020. The idea was a hit, and the self-proclaimed hippie added the Cannabis and Cannoli tour soon after. It was official: The Tye Dyed Tour Guide was born.
Tour Details
Jimbo leads two tours a day, seven days a week. Pizza, Beer & Paul Revere takes place from noon until 2 pm, and Cannabis & Cannoli runs from 2:30 pm to 4:30 pm. Be sure to book at least 24 hours in advance.
Tours cost $60 per person and are open to guests ages 21+. In order to make sure everyone has a top-shelf time, Jimbo limits every public tour to eight people. Private tours are available for larger groups.
He’s also available for guided experiences at Boston landmarks, like attending a concert at Fenway Park, touring the Museum of Fine Art, and arranging a private tequila tasting.
Jimbo’s Favorite Spots in Boston
- Boston Common
- Arnold Arboretum
- Commonwealth Avenue Mall during the spring magnolia bloom
- Piers Park at sunset
Jimbo’s Favorite Place to Travel
- “The Redwoods are so beautiful out west, from Oregon to San Jose. There’s magic in them thar hills!”
What are your favorite spots in Boston for cannabis and cannoli? Let us know in the comments below.
