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Life is Good hits the road with vacation packages

Life is Good Vacations will offer the opportunity to hike amid the grandeur of Bryce Canyon in Utah.Austin Adventures

It’s fitting that Life is Good, the iconic Boston-based lifestyle brand known for its optimistic slogans and outdoorsy bent, would venture into the travel sector. As the story goes, founders Bert and John Jacobs, who grew up in Needham, came up with the idea of selling T-shirts during a road trip from California to Boston in 1988, when the brothers were in their 20s.

For Life is Good Vacations, which launches this summer, the company turned to Austin Adventures, a family-run tour operator based in Billings, Mont., that specializes in small-group tours and customized adventure trips. The first branded outing is June 10, the six-day “Montana Vacation Package,” which includes rafting and hiking in Yellowstone National Park. (Adults, $2,698; single supplement, $580; children 12 or younger on “family” trips, $2,428). Other departures, seven in total, include the Canadian Rockies, Utah national parks, and Costa Rica.


So what distinguishes a Life is Good trip from Austin Adventures’ other similarly priced offerings?

“They’re not going to be significantly different because our trips always focus on positive energy and being unplugged and living in the moment,” said Kasey Austin, vice president of operations.

That said, the tour operator is altering the contents somewhat to emphasize Life is Good’s oft-promoted “Superpowers,” which include gratitude, authenticity, and courage.

For starters, groups will be smaller — 12 people maximum instead of 18 — though the guide ratio will remain at six guests to one guide.

“Smaller groups will provide a more intimate setting to allow guides to connect with guests and the guests to connect with each other,” Austin said.

Guides will receive extra training this spring from Life is Good “Chief Playmaker” and inspirational speaker Steve Gross, who runs the Life is Good Kids Foundation. (Austin Adventures will give the nonprofit foundation $100 for each Life is Good booking).


“Steve is going to work with guides to go over ways to connect with guests more closely through different activities, like ice breakers and games, whether in the van on the road or out on the trail. We were going to include only the Life is Good guides, then we thought, no, we want all our guides to be able to hear this. It will benefit everyone on all trips,” said Austin, who last year met with Gross at the company’s headquarters in the Fort Point neighborhood of South Boston. “His energy and enthusiasm about life in general got me so stoked.”

One of the ways Gross’s message will play out during Life is Good tours is when guests gather in the evening to share insights about the day.

“We’ll have laid-back times to talk and connect and reflect on the day and how we can carry optimism forward to progress and grow,” Austin said. “So these trips are a little bit more about bringing the group together, with a focus on optimism, not just on the trip but beyond it.”

But for those who might be getting worried, “We promise it won’t be singing and holding hands around the campfire,” Austin said with a laugh. “The goal is not to make people uncomfortable. No one will be forced to do anything, and there will be other ways to get people involved and to connect. It’s up to the guest.”

And the answer to the burning question?


“Of course Life is Good branded gear will be given out,” she said. “I’m not sure yet what it will be. But, yes.”

Diane Daniel can be reached at