Walk Your Laugh Off

Santa Barbara, put on your walking shoes.

Bear Cave Comedy has launched two new walking tours around town that combine great food, great locations, and great comedy. 

Haha’s and Tapas takes guests around local breweries, wineries, and eateries downtown, while Funny in the Funk is a chance to walk through the lively old urban wine trail. In April 2026, a guest wrote of Bearman: “She completely changed my opinion of Santa Barbara. Well done!” 

Get the history of The Granada Theatre while noshing on waffles from Goodland Waffles & Melts, or walk through El Presidio de Santa Bárbara while tipsy from a glass or two from Grassini Wines. 

Don’t just expect food and drink, either. These walking experiences put a spin on the traditional tour — combining popular sites with live entertainment. Fans love how experiential and immersive the two-hour tours can be — guests are encouraged to get up close and personal to some iconic spots, like walking to the tippy-top of the Santa Barbara County Courthouse Clock Tower. “We really want them to feel part of Santa Barbara,” says Samantha Bearman, owner and founder of Bear Cave Comedy. So, while you’re getting exposed to all the wonderful flavors and terroir of the region through food and drink, you’re also exposed to landmark buildings, art, and history — all while laughing. 

Each host is a comedian, drag queen, or drag king who puts wonderfully unique and hilarious spins on the typical tourist hotspots in town. “[Comedians] are getting a chance to directly connect with someone who can become a future fan,” says Bearman, a Santa Barbara native. Plus, “you’re making that person-to-person connection while getting in your steps.” 

These walking tours are the latest expansion from Samantha Bearman’s Bear Cave Comedy, an organization she started in the pandemic as a response to so much closure and uncertainty. Bearman, a behavioral wellness and alcohol and drug rehab specialist, had been side hustling as a standup comedian for years before 2020. When the world shut down and her job in healthcare left her furloughed, she opted to go all in on comedy. 

In the beginning, it looked like a series of virtual shows called “Comedians in the Kitchen,” where a chef and comedian taught groups to cook using simple tools and staple ingredients — in about an hour. She brought the series to universities such as Standard and San Diego State, but she craved even more. 

“The more flexible you are, the greater the chance for longevity,” she told me recently. That’s true of any business, but especially one in the entertainment industry, where Bearman herself often felt unseen and underrepresented. “When I [went] to shows, I never saw myself represented,” she says. A response to the overwhelming misogyny that many female comedians face in an industry dominated by men, Bear Cave Comedy didn’t wait for approval or funding — finding buy-ins from local businesses, thinking of new ways to reinvent the business, and exposing more people to local comedians — always anchored in the goal of getting underrepresented voices heard. 

Her company is creating more opportunities for those underrepresented — with tours offered every day of the week, sometimes multiple times a day, comedians are enjoying increased exposure while working on their craft. In a sea of gig workers in a challenging economy, this is no easy feat — Bear Cave Comedy is doing it beautifully. 

The team at Deep Sea Conway Family Wines on Santa Barbara Harbor were the first business to come onboard, and they became a catalyst for the business. Now she’s worked as far south as Ventura and north as Lompoc on trivia nights, comedy shows, stand-up sessions, and more. Her group regularly puts on “Comedy Is a Lucky Mic Trivia Club” at Uptown Lounge, hosts trivia “(for people who suck at trivia)” at Buddy’s Wine Bar in Ventura, and “Bingo for Baddies and Dance Party” with DJ Haley of the Hayfield on Thursdays at Seven Bar. They even developed a comedy camp, aptly named Bear Club Comedy Camp, in partnership with Santa Barbara Parks and Recreation, that promotes confidence and comedy in children ages 9 to 13.

“I feel like I’ve fallen back in love with Santa Barbara,” says Bearman. “I love being a tourist in your own city.” 

Everyone is welcome on tours, which are wheelchair accessible and dog friendly. Nonalcoholic options are provided at every spot. Tours typically last two hours, and groups range in size between two to 12 people. To learn more, or book a tour, visit bearcavecomedy.com.