How to Get Paid to Live Where Others Vacation: Tips & Tricks from a Traveling Chef

For most people, paradise is a vacation. A few fleeting days in the mountains, soaking in a spring, hiking into the quiet, or unwinding at a yoga retreat before heading back to the noise. But what if you could stay? What if you could live there—and actually get paid to do it?

That’s the question I asked myself years ago, somewhere between a yoga center in California and a farm in Hawaii. I’d been traveling, cooking, and offering my hands wherever they were needed. First through WWOOF—working in exchange for food and shelter—and eventually through paid roles where I was brought in for my skill set: chef, healer, organizer, problem-solver.

I’ve cooked in some of the most beautiful, remote corners of the world—not for luxury, but for community. For people on retreat. For those seeking something deeper. And I’ve learned this: there are hundreds of places—right now—looking for people like us. People who can cook, clean, fix, teach, nurture, and hold it all together behind the scenes.

These are some of the tips and tools I’ve used to turn my dream into a sustainable lifestyle.

1. Start with the Right Mindset

If you’re just starting out, you might think the only way to travel is by paying for it. But if you have a skill—cooking, massage, gardening, carpentry, hosting, teaching yoga, or even just being reliable—you can often exchange that for a place to live, a paycheck, and a lifestyle shift that most people never experience.

This isn’t about escaping the world—it’s about stepping into a better version of it.

2. WWOOF & Work-Trade Gigs (Great for Starting Out)

When I was younger and had fewer connections, WWOOF (Worldwide Opportunities on Organic Farms) was my gateway. You volunteer on organic farms around the world, and in return, you get room, board, and often some of the best conversations of your life.

It’s not always glamorous, but it’s real. I’ve pulled weeds in the Hawaiian sun, milked goats in Northern California, and harvested kale at dawn in Oregon—all in exchange for a bed, good food, and a deeper connection to the land.

WWOOF is ideal for beginners, but over time, I realized something: I had real skills. I could cook for 100 people on a tight budget, manage inventory, lead a team, and hold space during stressful events. I didn’t just want to trade—I wanted to build a lifestyle. That’s when I shifted to paid gigs.

3. CoolWorks.com: The Game-Changer

This site changed the game for me.

CoolWorks.com is a job board for seasonal and lifestyle-based work. Think retreat centers, hot spring resorts, national parks, ski lodges, remote restaurants, and glamping destinations. Many of the listings include housing—some even cover meals or travel. You can search by:

• Location (U.S. or international)

• Season (summer, winter, year-round)

• Job type (kitchen, housekeeping, maintenance, guest services)

• Housing provided (yes, please)

• Pet-friendly or not

• LGBT-friendly or “outdoor culture” workplaces

I’ve found everything from yoga retreat centers in the desert to eco-lodges in Alaska on this site. If you’re someone who can show up, do your job well, and live respectfully in shared housing, this is a goldmine.

4. Craigslist (Yes, Still Relevant)

It’s old-school, but still useful—especially for more off-grid or private gigs. I’ve found wild opportunities here: being a private chef on a hemp farm, caretaking someone’s property while they traveled for six months, and helping build out a food trailer in exchange for a place to stay and a chunk of ownership.

Pro tip: search using keywords like:

• “Caretaker”

• “Private chef”

• “Housing included”

• “Retreat center”

• “Off-grid”

• “Live-in”

You might have to dig. But buried under the scams and spam are true gems.

5. Indeed & Niche Job Boards

Indeed.com can also work if you search smart. Look for listings that mention “housing provided” or “relocation included.” High-end restaurants and resorts often offer apartments or shared housing for chefs and hospitality staff—especially in remote places like Jackson Hole, Big Sur, or Nantucket.

I’ve even negotiated airfare as part of my package when I was broke but excited about a gig. If they want you, they’ll often help you get there. Always ask. The worst they can say is no.

There are also niche sites for specific industries—like GoodFoodJobs.com for culinary and farm-to-table work, or Escape the City for more alternative professional paths.

6. How to Land the Gig: Connection Over Resume

Once you find a listing, don’t just apply cold. Take the time to research the organization. Read guest reviews, staff testimonials, blogs, even their mission statements. Find out what they care about.

Then send a short, thoughtful message introducing yourself. Let them know why you’re interested in their place specifically. Include your skills, your experience, and what you’re looking for. It doesn’t have to be long—just real.

A warm, intentional message goes much further than a generic application.

7. Life Once You're There

Once you land the gig, the real adventure begins. You’ll be living in places most people only dream of—soaking in hot springs at midnight, hiking alpine trails after your shift, dancing barefoot under the stars, or taking a yoga class before breakfast service.

It’s not always easy. You’ll share space. Sometimes there’s no Wi-Fi. Sometimes there’s too much community, or not enough. But if you’re wired for it, it’s magic.

And the best part? You’re not just passing through. You’re part of something. You're home—at least for now.

8. From Hustle to Lifestyle

Eventually, this becomes more than seasonal work. It becomes your lifestyle. You’ll build a reputation. You’ll have people reach out to you for gigs. You’ll start to string seasons together—spring in California, summer in Oregon, winter in the Southwest. You’ll build savings, find partners, and live in ways most people never even consider.

You might even land long-term roles with benefits, housing, and a cabin in the woods. It’s out there. I’ve lived it.

Final Thoughts

Getting paid to live where others vacation isn’t a fantasy—it’s a choice. One that takes curiosity, courage, and a bit of navigation. But once you say yes, the road opens.

Until then, I hope these tips help.

See you out there.