One Trip to St. Thomas Changed Everything: The Story of Barefoot Cowboy

Every unforgettable journey has a beginning, and for Barefoot Cowboy, that beginning was St. Thomas.

When guests step aboard our yacht, they're often curious about how a couple from Texas ended up living and working in the Caribbean. The answer is simple: St. Thomas completely changed the course of our lives. What started as a family vacation became a dream, then a business, and eventually the life we've always imagined.

And we can’t wait to share our story (and our adventure) with you!

The Vacation That Changed Everything

Years ago, before Barefoot Cowboy ever existed, I was living and working in Dumas, Texas. I decided to take my son on a vacation to St. Thomas, never imagining it would alter the direction of my life forever.

St. Thomas is home to the capital city of the U.S. Virgin Islands, Charlotte Amelie. It’s a gorgeous island with soft white sand, snorkeling and surfing spots for all ages, and restaurants you won’t be able to stop talking about (like Pizza Pi’s floating pizzeria).

We stayed at the Frenchman's Reef Resort, and by pure coincidence, one of my high school friends, Burt, had built a life in the Virgin Islands running day-charter excursions for cruise ship passengers. He offered to show us around, and in just one day we experienced some of the Caribbean's most iconic destinations.

We visited Foxy's on Jost Van Dyke, enjoyed drinks at the Soggy Dollar Bar, stopped by the legendary Willy T, jumped into the crystal-clear waters surrounding Norman Island, and snorkeled through sea caves that looked like something from another world.

By the end of the day, I was hooked. I knew when I went back home to my old life, I’d spend every minute dreaming of St. Thomas and the Virgin Islands. I wanted to make this place my home.

I remember telling Burt, "Keep an eye out for a boat I can live on."

Little did I know that simple conversation would become the beginning of Barefoot Cowboy.

Learning the Charter Business

Burt was the one who convinced me to get into the charter business. As he put it, “Why live on a boat in the Caribbean by yourself when you can share it with others?”

He introduced me to Randy and Shelly Tucker, owners of a monohull named Three Moons. They were preparing to retire from chartering and offered me a unique opportunity. I could bring friends down for a discounted charter, and if I purchased the boat afterward, they'd apply the charter cost toward the purchase.

I took the trip. Then I bought the boat.

At the time, I was still working offshore, so I hired an experienced crew to help operate Three Moons. But along the way, I learned everything from sailing techniques to boat maintenance, often joking that when I started, I still called every line on the boat a "rope."

Those years taught me how to captain a yacht. But more than that, they taught me how to create experiences that guests would remember forever.

When Everything Changed

After nearly five years operating Three Moons, Hurricane Maria struck the Virgin Islands in 2017.

The storm destroyed my boat and devastated the islands I had come to love. I was devastated, but like the Three Moons, I was crushed. My dream was over.

Like many people whose lives were affected by the hurricanes, I wasn't sure I'd ever return. I accepted a position overseas with British Petroleum as a maintenance supervisor, eventually working in Azerbaijan on offshore platforms.

Around that same time, life had another surprise waiting.

Natalie and I had been friends for years, going back to our school days. She hung out with my friends, and I hung out with her friends. She lived two blocks away from me. Our kids grew up together.

But it wasn’t until after I lost the Three Moons that things changed between us. We went on a few dates, and before we knew it, we were in love. My journey had always been about me. About my plans and my dreams for the future. But now, it was about Natalie.

We got married. As our new life together began, the charter business slowly faded into the background.

Until a trip back to St. Thomas changed everything, a second time.

A New Dream Arises

A close friend in the charter industry tragically passed away while preparing a boat for hurricane season. We traveled back to the Virgin Islands for his memorial service on Water Island.

Seeing old friends, walking familiar docks, and feeling the warm Caribbean breeze again reminded me of why I had fallen in love with the islands in the first place. The dream came rushing back.

Soon afterward, life presented another crossroads. BP wanted to relocate me to Houston, while Natalie had built a thriving business in Amarillo. At nearly the same moment, her company received an acquisition offer.

Instead of taking another corporate job, we chose something much bigger. We bet on ourselves.

Finding Barefoot Cowboy

We began searching for the perfect catamaran. We knew we needed a boat designed to give our guests the best experience possible on their journey.

We wanted spacious gathering areas where families could laugh together, quiet corners where someone could escape with a good book, comfortable cabins with private bathrooms, and plenty of room for everyone to spread out.

After missing out on one boat, another appeared just days later: a Leopard 58 that checked every box.

We knew immediately it was the one.

Today, that yacht is known as Barefoot Cowboy.

The name itself reflects who we are. It combines our Texas roots with the relaxed, barefoot lifestyle of the Caribbean. It was also inspired by a beloved Amarillo-owned barbecue restaurant on St. John that was destroyed during the hurricanes, a fitting tribute to both places that shaped our story.

More Than a Charter

When you look into booking a private charter in the Virgin Islands, you'll find plenty of massive, corporate fleet companies out there. But when you step onto the Barefoot Cowboy, you are stepping into a dream that Natalie and I lived, lost, and rebuilt from scratch.

We don't just hand you the keys or hire a rotating crew; we are true owner-operators. We are right there with you every single day of your trip because we remember exactly what it felt like to have our breath taken away by these waters for the very first time.

Our absolute passion is recreating that exact "aha!" magic for you. Because it's our boat and our business, we don't follow a rigid corporate schedule. If you fall in love with a certain beach and want to skip the next island to stay put, we stay put. It’s your charter; we just live in it!.

Total Peace of Mind on the Water

A lot of people are intimidated by the idea of chartering a boat because, as we love to say in the industry, "everything's broken on a boat, you just don't know it yet."

But because of my extensive background as a BP offshore maintenance supervisor, you get total peace of mind. I know exactly how this boat feels, and I handle repairs seamlessly behind the scenes. Last season, we actually pulled a transmission and replaced a seal while our guests were enjoying a taxi ride ashore, ensuring their dream vacation wasn't interrupted for a single minute.

From Natalie’s incredible plated meals and our signature Texas Panhandle-style margaritas to evening board games and our favorite tradition of sharing the day's "roses and thorns" over dessert, we treat you like family. Whether it's guiding your kids through their very first snorkeling experience or finding that perfect quiet anchorage, we tailor everything around your happiness.

The Adventure Continues

St. Thomas will always be where this journey began.

It's where a Texas vacation turned into a lifelong passion and where one incredible day sparked a dream that survived hurricanes, career changes, and thousands of miles.

Today, we have the privilege of sharing that dream with every guest who steps aboard. We can't wait to welcome you to Barefoot Cowboy, show you the islands that captured our hearts, and help you create a story you'll be telling for years to come.