For most Boston Swifties, the morning after the rainstorm that almost upstaged the Taylor Swift concert was one filled with fatigue, hoarse throats and new friendship bracelets. For Tommy Collins, it was filled with wet socks and shirts left under the seats of his trolley bus as he was preparing to head to Foxborough and do it all over again a few hours later.

No, Collins doesn’t own a Taylor Swift Tour trolley. Maybe you recognize his trolleys from seeing them in the Southie St. Patrick’s Day Parade? He owns Mobsters and Lobsters, the private event tour company that takes you through the historic sites of Boston mob tales and ends with an optional lobster dinner. But, if going to a concert or a Red Sox game is more your speed, you can rent one of the trolleys and have them take you there too. They even drive wedding parties to the ceremony and reception!


Eight years ago, Collins was driving a historical tour guide truck for a company where a woman was renting trolleys for her own up-and-coming business, Mobsters and Lobsters. Next thing you know, the Southie native with the rugged Boston accent was recruited by her to write a script, come up with a route and drive the rented trolley with an M&L banner hanging over the side.

After four years, he officially bought the trademark. Mobsters and Lobsters was officially his. The next order of business? Get his own trolley. But, just as the final touches were being made and the wheels were ready to roll, the COVID-19 pandemic came in full force, shutting down the tour industry for the unforeseeable future.

Loans and debt started to pile up and the Collinses weren’t sure if Mobsters and Lobsters would survive.

With a little help from Massachusetts native and Barstool Sports Founder Dave Portnoy, they were given another chance. The sports company was giving out loans to small businesses who put in an application. After months of not hearing back, Collins decided to send it in one more time.

As he was walking the aisles of Home Depot with his wife Tory (who happens to be the brains behind the operation), looking for yet another home improvement project to keep them busy during lockdown, they got an unknown Facetime call. They were told in the application process that if they ever got a call from a number they didn’t know, to pick it up because it would be Portnoy.

And what do you know, it was.

“Shut the fuck up,” Tory Collins said in the paint aisle.

Portnoy said he loved their logo and that they should receive some funds within 72 hours. They received $7,500 a month for almost a year and were one of 328 businesses chosen by The Barstool Fund.

Largely in part to that, Mobsters and Lobsters has grown to what it is today.

After 8 years and 409 reviews on Tripadvisor, 407 of them are “excellent,” and 2 are “very good”. Collins said the fact that there are no bad, poor or terrible reviews, especially in the tour business, is unheard of and something he prides himself in.

He also prides himself in his colleague and other driver behind the wheel of the trolley. Gary Bolles, another Southie native, went from seeing the Mobsters and Lobsters trolleys driving through the streets of Boston to being the one driving them through the streets of Boston.

Bolles joked, “I don’t know if [Tommy and Tory] could live without me, they love me so much.” Luckily, the feeling is mutual, as Collins said, “Gary is one of the best things that happened to us, finding him.”

The social media comic loves joking with his riders and working the room – or rather, the trolley.

If you are from New York, you’ve probably been told to get off the trolley if you are a Yankees fan – don’t worry, he doesn’t totally mean that. And if you ask him why he isn’t wearing the lobster costume, the 6’2”, 290-pound driver will tell you he’ll wear one if you find one that fits. Although riders dine at Venezia’s in Dorchester for their lobster dinner, Bolles said he’s been sticking to salads there recently with the goal of wearing the lobster suit in the back of his mind.

Between the two of them, their favorite part of the job by far is the people. Bolles got to meet the niece of one of the 11 robbers in the Brink’s Job in 1950 and gave her information about her own uncle that she didn’t even know. Collins has experienced customers turn into friends, like Red Sox Pitcher Kutter Crawford’s family. One of his most recent tour groups was the head coaching staff of the Pittsburgh Penguins, so naturally, Collins had to wear his Bruins jersey and rip on them the entire time. That was one of his favorite rides to date.

The new people they meet every time they step onto that trolley make the routine tour anything but monotonous. It never gets old.

“I have the best job in the world. In 8 years I’ve never gone to work saying, shit, I have to go work today,” Collins said. “It’s been an amazing ride, beyond my wildest dreams.”

If you’re looking for a fun holiday activity to do with family or friends, be sure to check out their South Shore Sights and Lights rides, where you can BYOB, enjoy a nice dinner and see the festive lights! Otherwise, their Mobsters and Lobsters tours are available for bookings year-round.

Buckle up and crack open a cold one on your way to cracking open a claw.


  1. Meaghan Collins September 17, 2023 at 10:35 am - Reply

    I’m so proud yo be your daughter! love you!

  2. Maria Cusano September 17, 2023 at 4:35 pm - Reply

    Took the trolley to and from ZBB concert at Fenway this past August! All we can say the ride wad epic!! What a blast!! Thx Mobsters & Lobsters!!

  3. Robin Hulshizer September 22, 2023 at 10:55 am - Reply

    We loved the Xmas light trolley so much last year that we are headed to it again this year, but with 10 friends from Chicago in tow! Tom and Tori Collins are so special – salt of the earth, grounded, kind and funny as heck!

  4. Victoria Collins October 10, 2023 at 4:56 pm - Reply

    Awww thank you guys! We are so grateful to get to meet such incredible people!

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