As most Door County residents prepare for the long haul of winter, Nick Steingart is packing his bags and eyeing up the space in the back of his white 1998 Volvo wagon parked in the mud behind his small shack of an apartment in Ephraim.

When the calendar flips to November, he’ll hit the road for his seventh winter season at Vail Resorts in Colorado, and he won’t be alone.

A gaggle of fellow Door County workers will meet him there, while others will head to warmer climes in Florida, South Carolina, or Texas. They’re part of a tourism industry sub-culture, the vagabonds who piece together a living by bouncing from one locale to the next, guided by the seasons.

“I’ve never been in Door County in the winter,” Steingart says, “and I’ve never been in Vail in the summer.”

The New Berlin native was still guided by the rigid path that goes college, career, wife, then kids when he was introduced to Door County by a friend.

“I was going to school and working as a landscaper in Oshkosh, making about $8 an hour, when Matt Joswick invited me to visit him at Camp David in Fish Creek,” Steingart remembers. Camp David is a concert barn with summer housing on County F outside Fish Creek. His eyes grow wide as he recalls the impression the visit made on him.

Nick Steingart

“I’m meeting these people who are sailing during the day, and making $100 a night waiting tables,” he says, the awe still alive in his voice seven years later. “I’m like, ‘what the heck am I doing in Oshkosh?’”

His notions of what he wanted to do with his life were beginning to change, and the visit to Door County hammered it home.

“I came to the point where I thought, life is short, and I want to cram as much fun into it as possible,” he says.

He finished his degree in environmental geography and began spending his summers working, sailing, and playing music in Door County with his band, The Nicks. When winter comes, he heads to Vail to work as a ski instructor.

Mike Termini fell into a similar routine. The 30-year-old grew up in Door County, spending his high school years cooking in the frenetic kitchen at Al Johnson’s Swedish Restaurant in Sister Bay.

He was 21 when he decided to follow some friends down to Florida to work for the winter. He wanted a change of scenery, the beach, and the income that’s hard to find in Door County restaurants when winter arrives.

He hooked up with the Door County connection in Fort Meyers Beach, where dozens of the peninsula’s servers head for the winter, and where the reputation of the Midwest worker precedes them.

“The connection with friends is big, but once the manager hears you’re from Door County, you’re pretty much in,” Termini says.

For those who head south, timing is everything. There is a strong pull to pack up as soon as the final Fall Fest bloody Mary is emptied, but that can be costly. Like Door County, the window to make money in Florida is short. Business picks up over Thanksgiving, then flatlines until the holidays. Heading down too early can be costly.

“You have rent going out, maybe a security deposit, and you just spent the money to get down there,” Termini says. “Then you’re not making real consistent money for a couple months.”

He compared November and December in Fort Meyers to the late spring season in Door County, where hopeful workers and business owners see dollar signs in May, only to be teased by Memorial Day and on the edge of broke until July 4th weekend.

“You have to be fully staffed for the holidays down there, just like Memorial Day here, but then there’s not enough work to go around for a few weeks,” he says. But the hours aren’t easy to find in Door County in November and December if you stay, so Termini learned to diversify.

“If you have enough connections, you can cobble together enough hours to make money in Door County through the holidays,” Termini says. Besides cooking, serving, and bartending, Termini has worked with a mason hauling rocks, for a tree-trimming service, and even house-sitting to keep money coming in. It’s a “career” familiar to many on the peninsula, where a business owner might moonlight as a server for her friend’s restaurant, or a bartender will supplement his income by roofing during the day.

“You have to be a kind of jack-of-all trades,” says Steingart, as he rattles off an endless list of the odd jobs he’s had over the years. He’s been fortunate to have the same job waiting for him each winter when he goes to Colorado. The season in Vail is a little longer and more consistent than in Fort Meyers, which means he can take off when November arrives and count on paychecks coming in steadily within a couple weeks.

This year, Termini will stick it out through the winter in Door County. In 2007 he earned his Realtors license, figuring he could couple that with work as a server to make a year ‘round living on the peninsula.

“When you’re younger, it’s kind of exciting, the uncertainty,” he says. “But as you get older that’s kind of the problem. It starts taking its toll. You get sick of packing up your life every six months, paying double rent, and living that sort of a vagabond lifestyle.”

The crash of the real estate market put a hitch in his plans, so he still makes his living from bartending and serving, while also working in real estate for Coldwell Banker in Fish Creek. He’s not sure that this is how to make it work, but he loves Door County, and like so many, he’s trying to be creative enough to put it together here.

Steingart, meanwhile, prepares to make the transition again. At 33, without a wife or kids, he still looks forward to the change. Every six months, he says, brings rejuvenation.

“There’s a really good feeling when I leave Door County in the fall,” he says. “When the leaves fall off it is time for me to leave (no pun intended), and when the snow melts it’s time to come back. Just when you start to get rattled, you get to do something new.”

Last year he spent 106 days on the slopes skiing or teaching kids to ski, he spent another 70 sailing, and played 80 gigs. It’s a stat sheet that makes his more traditionally employed friends jealous.

“‘You’re so lucky!’ they say when I see them,” Steingart says. “I am lucky, but I don’t know if this is how to do it either.”

He’s not looking forward to leaving his girlfriend for the winter – she recently found a job that will take her through the winter in Door County – or his friends.

“Everybody sacrifices something,” he says. “For me it’s stability. To be perfectly honest, I have plenty of days where I say to myself, ‘What am I doing?’” But sticking around in either place all year really isn’t much of a discussion. “How am I going to make money up here in the winter?”

Like so many who stumbled into life in Door County, his roots never grow too deep.

“Part of me feels I should be doing something else, part of me thinks I’m doing exactly what I should be,” Steingart says uncertainly. Then he leans forward, the doubt gone. “I do know that I’m supposed to be playing music.”

Something solid in the uncertain world of piecing together a living in Door County.