Joanna, Jennifer and Kyle Wulffenstein take a break to pose while on the job. The mother-children trio have been driving busses in Skagway since 2009. Jared Martin

Traveling family from Oregon now works along side eachother giving tours in town


Unlike all the other tour guides who work during the summers for Holland America Princess Alaska-Yukon, when JoAnna Wulffenstein wants to say hi to her family, she doesn’t need to call, text or write. Instead, she keeps an eye out for two specific co-workers driving tour buses alongside her, and waves.
Despite the multitude of adventurous 20-somethings and college students known for driving tour buses in Skagway during the tourism season, the Wulffensteins – JoAnna, her younger brother, Kyle, and their mother, Jennifer – have been driving together since summer 2009.
“It’s an easy and fun job,” Kyle said. “I’ve always been outdoorsy, which was one of the things that drew me here.”
Although HAP Alaska-Yukon has siblings as employees, the Wulffensteins are the only multi-generation family working as Skagway driver guides for the company.
“I’ve gotten to know my kids better working here,” Jennifer said. “I’ll point them out to my passengers if I see my kids on my tours. I’ll say, ‘Hey guys, that’s my son and daughter. Isn’t he handsome? Isn’t she beautiful?”
Having mom around when one is sick or in need of a little love is especially nice, Jo said.
“The other day when I was doing a tour in Liarsville, I was dying because I was so hungry,” Jo said. “My mom was stopped there with her tour as well, so I hopped off the bus and said, ‘Mom, can I have some money?’” She gave me some change so I could buy myself a snack. This is one of the reasons why I love having my mom here.”
All three give tours in Skagway, and as far as Caribou Crossing Trading Post in the Yukon Territory. Jo also trains incoming drivers in the off-season, and evaluates drivers during the summer — including her mom and brother.
“I was surprised by how outgoing Kyle is when I did his audit, because usually he’s so soft-spoken,” Jo said.
The family, originally, from Turner, Oregon is used to doing adventurous things at the same time. For example, the three of them embarked on two-year missions with their church at the same time, however each one of them went alone and to different places — Jennifer stayed in the U.S., while Jo traveled to Albania, and Kyle went to Costa Rica.
But even though they have a history of choosing to do things together, if you ask Jo, she likes to joke that Kyle and Jennifer followed her to Alaska. Jo, 26, fell in love with this state when she came to work at Alyeska Resort in Girdwood as an 18-year-old. She continued to work at the resort almost every summer, until a friend suggested that Jo would make a great tour guide.
Jo said she researched Skagway, eventually making the town her new summer destination to become a tour guide for the company that is now HAP Alaska-Yukon.
“I’m very outgoing, and I never shut up,” Jo said. “I love driving. My favorite part is developing relationships with people. Sometimes, I almost cry when I’m dropping off my passengers in Fraser, [British Columbia].”
And Jo’s track record with passengers proves that she is gifted at what she does. Hanging in the HAP Alaska-Yukon’s office at First and Broadway is a painting fit for a museum: a portrait of a young woman with mocha-colored hair and twinkly eyes—the jagged Sawtooth Mountain peaks in the distance, behind her.
It’s a portrait of Jo, painted by an artist who rode one of her tours and then weeks later, sent her the work of art in the mail as a token of appreciation. This is one of only many gifts that she’s received over the summers. Jo is the most experienced driver guide, however, each Wulffenstein brings something a little different to the tourism trade.
“I think I excel at just being welcoming and at ease with people,” Jennifer said. “I’ll find ways to make it fun with candy or little games and things like that.” Although Jennifer and Kyle aren’t sure of their plans for next summer, both of them said they expect to continue traveling and having new experiences. Kyle said he would love to continue to work in Alaska, and Jennifer would love to travel to the east coast.
JoAnna on the other hand, definitely plans on returning to Skagway next year, as she’s been doing for almost half a decade.
She said it’s her family that, in many ways, has contributed to her success here. After all, Jo said she was given her mother’s free-spiritedness, her father’s outgoing personality, and of course, a touch of the adventurous independence that can only be the trait of a Wulffenstein.