Let’s be honest, we’ve all had that daydream. You know the one. You’re sitting under fluorescent office lights, staring at a spreadsheet that refuses to balance, and you think, “I should just quit everything, move to an island, and drive a boat.” Or maybe just eat pie for a living.

Most of us snap out of it, grab another lukewarm coffee, and go back to the grind. But not Kim Stamps.

Kim is the kind of person who actually did the thing. She took a look at a future filled with pantyhose and cubicles, said “hard pass,” and built a life in Key West that revolves around storytelling, history, and—perhaps most importantly—rum and pie.

I recently caught up with Kim on the Fun in Key West podcast (we’ve known each other for about a decade, which is like a century in Key West years) to talk about her wild ride from finance major to tour guide extraordinaire. If you’ve ever wondered what it takes to pivot your life completely or just want the inside scoop on the best walking tours in the Conch Republic, grab a drink. You’re going to want to hear this.

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The Finance Major Who Refused the Cubicle

If you met Kim today, breezing down Duval Street in flip-flops with a group of happy tourists trailing behind her, you’d never guess her background. She actually holds a finance degree.

Yeah, numbers. Stocks. The whole nine yards.

“I decided not to go into that world,” Kim told me, laughing about the bullet she dodged. “I didn’t want to work in a cubicle 90 hours a week.”

Can you blame her? Instead of settling for the corporate ladder, a friend tipped her off about a school in San Francisco. And no, it wasn’t business school. It was Tour Guide School.

(Side note: Did you know Tour Guide School was a thing? Because I didn’t, and now I’m wondering if I can enroll just for fun.)

“It’s actually the International Tour Management Institute,” Kim explained. “It’s prestigious. They taught us how to conduct tours anywhere in the world to places we’d never been.”

They trained her to research, adapt, and lead groups through the unknown without breaking a sweat. And she didn’t just stay local. Kim spent years as an “adventure tour guide,” driving small groups across the entire country—hitting every state except five, plus parts of Canada.

This was the old-school days, folks. We’re talking pre-GPS. Pre-smartphone addiction. “We were off-grid basically,” she says. “I had to do a crash course every morning on where we were going. I had a cell phone, but it only worked in the city.”

Imagine navigating a van full of tourists across the Rockies with nothing but a paper map and your wits. That’s the kind of grit you can’t learn in an MBA program.

Building “Up The Keys” (and Surviving the Storms)

After years of living out of a suitcase on the road, Kim settled in Key West about 18 years ago. By 2016, she was ready to launch her own baby: Up The Keys.

It was a brilliant concept—eco-tours focusing on wildlife, conservation, and that “road trip with friends” vibe that she had perfected during her cross-country guiding days. It was her passion project. But here’s the thing about owning a business in paradise: Mother Nature doesn’t care about your business plan.

In 2017, Hurricane Irma hit.

If you weren’t here, it’s hard to explain the devastation. Irma didn’t just knock over a few patio chairs; it completely annihilated Kim’s touring grounds up the Keys. “There was really no way to change locations,” she recalls. “All of the Keys were ruined.”

Most people would have packed it in. Kim? She pivoted to volunteering (she actually called it Voluntouring because she brought groups along), helping the community rebuild, and slowly pieced the business back together. She hit record months. Things were looking great.

Then came 2020. The pandemic. The world shut down, and the wheels on the tour van stopped rolling.

But here’s a little secret about Kim: she doesn’t stay down. When the world started creeping back open, people were terrified of enclosed spaces. Nobody wanted to sit in a van with strangers breathing the same air. So, she ditched the wheels.

“I started doing walking tours because people didn’t want to get in the van,” she says. And just like that, a new chapter started. She eventually sold the Up The Keys van tour business to a lovely Canadian couple (who are crushing it, by the way) and went all-in on foot traffic.

Walking on the Dark Side: iWitness True Crime

Now, let’s talk about what she’s doing today, because it is juicy.

Key West has a million ghost tours. You can’t throw a rock without hitting a trolley claiming to know where Robert the Doll’s spirit is hanging out. And those are fun, don’t get me wrong. But Kim wanted to do something different. Something real.

Enter the iWitness True Crime Tour.

“We’re basically bringing crime alive in the streets of Key West,” Kim says. “It’s not just listening to stories about the past. It’s expect the unexpected.”

I took this tour recently, and let me tell you—it’s not what you think. You’re not hunting for ectoplasm. You’re diving into the gritty, scandalous, and sometimes bizarre history of crime on the island. We’re talking about real headlines from the Key West Citizen and the Miami Herald.

“Unfortunately, there’s a significant amount of crime in Paradise,” Kim admits. “It’s not a lot of violent crime, fortunately. But we dig deep.”

They cover the bad cops of yesteryear (don’t worry, we love our current officers), the scandalous cover-ups, and the stories that usually get swept under the rug because everyone wants Key West to look like rainbows and butterflies.

The best part? The reactions. Kim told me about a guest recently who spent half the tour hiding behind her husband. “I’m like, job well done, Kim,” she laughed. “It’s not because it’s a scary tour, necessarily. It’s just… you don’t know what to expect. There are surprises along the way.”

(I’m not going to spoil the surprises, but let’s just say things happen during the tour that might make you question who is part of the show and who isn’t.)

Right now, the tour runs at 8:00 PM—perfect for that eerie nighttime vibe. It’s about 90 minutes, covers roughly nine blocks, and ends conveniently close to Duval Street, so you can go grab a stiff drink immediately after. Because trust me, after hearing some of these stories, you might need one.

[Book your spot on the iWitness True Crime Tour here]

Tart Tales: The Sweetest History Lesson

If murder and mayhem aren’t your vibe (or if you just really, really like dessert), Kim has another trick up her sleeve: Tart Tales.

This is the tour I recommend to everyone who claims they “don’t like history tours.” Why? Because there is pie.

“Key Lime Pie has history,” Kim explains. “It dates all the way back to the 1800s here in Key West. The limes go back even further, to the 1400s.”

On this tour, Kim or her business partner Yvonne take you on a culinary stroll to sample the goods. They hit up three different spots—sometimes restaurants, sometimes pie shops, sometimes bars. And they don’t skimp.

“We’ve asked our pie shops to give us half slices, and they’re awfully generous,” Kim warns. “Be prepared to eat some pie.”

But it’s not just a sugar coma waiting to happen. They carry iPads loaded with historical photos to show you what the Seaport used to look like while you’re standing in the exact same spot today. You learn about the culture, the architecture, and yes, the controversy over who actually invented the pie.

(Kim’s dream guest for the tour? Aunt Sally, the woman credited with the recipe. “It would be really nice if she would come in and talk to us,” Kim jokes. “We could transport her in time.”)

And because this is Key West, the tour ends with a rum cocktail. Obviously.

“Everything is good with Key Lime Pie and rum,” Kim says. And honestly, I have never heard a truer statement in my life.

[Book your spot on the Tart Tales Tour here]

The “Local” Perspective

One thing I love about Kim’s approach is that she isn’t just reciting a script. In fact, there is no script.

“It’s not a script,” she emphasizes. “We don’t have to stay on the script in order to conduct this tour. Everyone is a little bit different because we know the information.”

That means if you ask a question, the tour might veer off in a fascinating new direction. If a local walks by and shouts hello, that becomes part of the experience. It feels less like a lecture and more like you’re walking around town with a really smart friend who knows all the skeletons in the closet (literally and figuratively).

She’s also a goldmine for local recommendations. I asked her the dreaded question that every local hates: Where should I eat?

Her answers were solid:

• For Happy Hour: The Boathouse. “Beat the Boathouse,” she says. Good for dinner, legendary for happy hour.
• For Fine Dining: Cafe Sole. Specifically for the Hogfish dinner.
• For a Foodie Adventure: Little Pearl. She calls it “a party on your tongue.”

See? This is why you take a tour with a local. You get the pie, the crime, and the dinner reservations sorted out in one go.

There’s Always Time for Lime and Crime

Kim’s journey from a finance major to a tour guide icon is a masterclass in just going for it.

“I looked at a picture of Monument Valley with a tour group… and I said, ‘I wanna be that guy,'” Kim told me, remembering the moment she decided to change her life. “If you find something that you really feel strongly that you want to do, you can do it. You just have to go for it. Run to it.”

Whether you’re a local who has never explored your own backyard or a visitor looking for something deeper than a T-shirt shop, Kim’s tours offer a slice of the real Key West. It’s gritty, it’s sweet, and it’s a hell of a lot of fun.

As Kim likes to say: “There’s always time for Lime and Crime.”

She’s currently working on getting her tours onto the cruise ship excursions (pro tip: book early if you’re cruising in!), and she’s even crafting a daytime version of the crime tour for those who are afraid of the dark.

So, next time you’re on the island, skip the tourist traps. Go walk the streets with the woman who knows where the bodies are buried—and where the best meringue is hidden.

Ready to walk it off? Book your Tart Tales or iWitness True Crime tour right here.