Seasonal Jobs: Why Live and Work in One Place?

Downtown Skagway, Alaska. photo.
Downtown Skagway, Alaska. photo.

More Than a Tourist: Life as a Professional Vagabond

By Kay Vandette

 Meghan O'Toole Gott, also known as Moonshine Meg, in costume at the Liar's Gold Rush Camp in Skagway, Alaska, where she had a seasonal job.
Meghan O’Toole Gott, also known as Moonshine Meg, in costume at the Liar’s Gold Rush Camp in Skagway, Alaska, where she had a seasonal job.

Picture this: Summers spent in Alaska, enjoying breathtaking mountain vistas and opportunities for endless adventure.

Imagine winters spent on tropical beaches in the Caribbean or Hawaii, palm trees rustling in the breeze and waves lapping the sand. Or maybe you would prefer to go to Colorado or Montana, to ski and frolic in the snow. Sound too good to be true?

Welcome to the exciting world of the professional seasonal worker. Being a seasonal worker can give you unique access to popular travel destinations, the chance to connect with a wide network of world travelers, forge lifelong friends, see and do things off the beaten path, and expand your world view.

A Seasonal Worker’s Life

In this article, I’ll detail my own experiences as a seasonal worker in Skagway, Alaska, and talk about the many challenges and perks that come with spending a summer or winter away from home.

I’ll go over some typical seasonal circuits and you’ll hear from professional vagabonds who make a living traveling.

After working in Skagway, Alaska for a couple of summers, the grandeur of the mountains and the adventurous spirit of the people I met was forever etched in my memory. Skagway is a small town in Southeast Alaska, about 7 hours by ferry from Juneau and 20 miles from the border of Canada.

You sometimes have to trade a view like this in Alaska for good Wi-fi.
You sometimes have to trade a view like this in Alaska for good Wi-fi.

There, I took my first dip in the ocean, hiked up a mountain, and drove a Jeep in the wilds of the Yukon.

I spent my most memorable summer working at a Gold Rush Camp called Liarsville as a Madame.

They called me Luscious Lulu. I had no Gold Rush know-how, but I spent my days putting on 3-4 shows a day, teaching tourists how to pan for gold, and inviting people to take a step back in time for a few short hours and learn the history of Skagway.

It was a job like no other. But don’t worry, if dressing up in costume and performing isn’t to your taste. There are tons of jobs available for seasonal employees.

 Website Job Listings

You can look on websites like Cool works ( or Seasonal employment ( to find multiple job listings. The work might range from tour guide to a bus driver, bartender, mountain guide, ski instructor, or barista.

The Liarsville Gang are all seasonal workers, in Skagway, Alaska. Lisa Ann Gaylord photo.
The Liarsville Gang are all seasonal workers, in Skagway, Alaska. Lisa Ann Gaylord photo.

Any job in the service and hospitality industry is fair game. Seasonal workers are in demand when tourism for a particular destination hits its peak.

One of my fellow Liarsville actors, Tim Sislo, spent two years going from Alaska in the summer to Colorado for the winter. Meg Mullins, another Skagway friend, wintered in Hawaii after her summers in Skagway.

Tim is a Wisconsin native, who after working as Tumbleweed Tim in Liarsvillle, was a tour guide for the White Pass and Yukon Railroad in Skagway and a driver in Vail.

Meg has worked as a barista for White Pass and Glacial Smoothies, a local Skagway hotspot, and also performs standup comedy on her travels.

New Things to Experience

Tim says that trying new jobs and keeping busy are some of the benefits of seasonal work. Even if you have a job lined up, just living in a new town might open up new things.

In Meg’s case, it was performing standup comedy. You might find yourself playing with a local folk band, getting part-time work as a gardener, or apprenticing with a local artist.

Once you have a job lined up, what you can expect for housing? Finding work and housing in Skagway is fairly easy. A good majority of employers offer housing. The big tour companies are specially equipped with furnished housing.

Skagway's mountainous landscape in Alaska.
Skagway’s mountainous landscape in Alaska.

But looking for work in winter may be a bit more challenging. And even if you find a job, Tim says that housing is the real problem.

In Denver and Vail, where he has gone for the winter, employee housing isn’t as available, and according to Tim, you might expect to pay $600-$900 a month for an apartment.

A necessary sacrifice for the avid skier looking for five-star access to the slopes. But what about in Hawaii or the Caribbean?

Meg Mullins came from Georgia before she fell in love with Skagway. She says that you might find the opposite experience in Hawaii as opposed to Colorado. That being, cheaper housing but getting the job is trickier.

She said “Housing was surprisingly easy, though. Craigslist helped me land a room in a bungalow on the water for $500 a month. The same price I paid for a room in Skagway.” Meg did go on to explain that she worked on a smaller island, but the bigger cities and islands might have more options for work and housing.

With seasonal work, you can expect to lose a few comforts of home. My first summer in Alaska was an adjustment because I didn’t have access to the internet. A small price to pay for having my morning coffee looking at the mountains. Tim says that it’s important to make whatever space you are given your own, whether that’s a room with three other people or your own bungalow.

Keepsakes are Helpful

Packing a few keepsakes and photographs may seem like a waste of precious suitcase space, but it will help on those days when you feel the pangs of homesickness. Meg loves getting care packages from home, and it shows how much her family loves and supports her.

Downtown Skagway, Alaska. Kay Vandette photo.
Downtown Skagway, Alaska. Kay Vandette photo.

Despite the lack of a few luxuries, a life away from home, and being constantly on the go, there’s a reason college kids run away to the Land of the Midnight Sun and beyond.

I’ve even met several older retirees looking for an alternative to typical retirement options. They would drive the country in an RV and work a season.

That gives you an idea of how varied the people are. It’s not about the job, even though making a little money is nice. It’s about the scenery and the people you meet.

The scenery can be overwhelmingly beautiful. Being surrounded by forests, the ocean, and mountains my first days in Alaska made me realize how little of the world I had actually visited, and how happy I was to live in this corner of the world, even temporarily.

More than the scenery, you forge connections with people all over the world. No cliques here, just adventurous spirits not ready to settle down or still looking for, as Tim says, “They are forever home.” The easiest way to land a seasonal gig is by word of mouth.

Social Media for Job Listings

Social media can light up job openings in a new destination. Meg Mullins said it best when it came to her new circle of world traveling friends: “All of the sudden your (Facebook) news feed is flooded with African sunsets and cocktails in Bali. All at once you belong to a community…” A community of travelers fueling their wanderlust by seeking experiences out of the ordinary.

Tim recounted to me an amazing experience he had his first summer in Skagway. He and some friends got the opportunity to stay on a houseboat and go to the Southeast Alaska fair in Haines, Alaska. An experience only possible because of the leap he made to work in Skagway.

Skagway seems to have a particular hold on the seasonal employees lucky enough to find themselves there. Tim admitted that “I like moving around, (but) summer is always Skagway.”

Seasonal work isn’t for everyone. While you may get to experience things the tourists don’t or get offers for excursions at a discounted price, you are still there to work. But, if you can put up with a few inconveniences, work longer hours, and commit to a summer or winter away, it’s an experience like no other.

The coast of Alaska near Skagway. A great place to be a seasonal worker, says the author. Kay Vandette photos.
The coast of Alaska near Skagway. A great place to be a seasonal worker, says the author. Kay Vandette photos.

You get to truly learn about a place, its history, the best restaurants, bars, hikes, and shops. And more than that, the people you meet will stay with you forever. I worked two summers in Skagway, and when I went returned, the town and my fellow vagabonds welcomed me back.

I still hear the mountains calling and maybe I’ll find myself in Alaska or in another corner of the world for a new adventure next season.

Kay Vandette


Kay Vandette is a freelance travel writer and vagabond. She currently works for an online travel booking site and especially enjoys writing about her Alaskan adventures. 

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