About Us

About US

Get Away to Your Perfect Getaway with Barefoot Cowboy

Most Caribbean vacations are limited. With Barefoot Cowboy, the only limitation is your imagination.


Our crew lets you customize virtually every aspect of your vacation, so you can kick off your shoes and unwind—your way.


Get Away to Your Perfect Getaway with Barefoot Cowboy

Most Caribbean vacations are limited. With Barefoot Cowboy, the only limitation is your imagination.


Our crew lets you customize virtually every aspect of your vacation, so you can kick off your shoes and unwind—your way.


layered photos of two men and a woman n a boat and overhead view of the boat
Group photo of Roy Pat, Natalie, and Madeline near the ocean

We Bring Your Dream

Caribbean Escape to Life

Most Caribbean vacations are limited. With Barefoot Cowboy, the only limitation is your imagination.


Our crew lets you customize virtually every aspect of your vacation, so you can kick off your shoes and unwind—your way.


We Bring Your Dream

Caribbean Escape to Life

At Barefoot Cowboy, we understand that cruises can be disappointing when it feels like your trip was made for someone else. After how stressful this year has been, you deserve a chance to get away and unwind—without worrying about sticking to a strict itinerary.


Barefoot Cowboy allows you to design every aspect of your trip, including food and drinks, destinations, activities, and the schedule. Our catamaran can comfortably accommodate you and up to 9 guests.


Unlike other charters, Barefoot Cowboy is operated by its owners. That means the same people who help you book and plan your perfect vacation will be with you every step of the way. Whether this is your first charter adventure or your tenth, we’ll make sure your vacation is just right.


Why Go Barefoot?

Safety is a top priority.

Every member of the Barefoot Cowboy crew is vaccinated and we’re taking extra precautions to keep the boat clean, so you can unwind and feel safe at the same time

We’re there for you every step of the way. From picking you up at the dock to making sure you get where you need to go when your trip ends, we’ll ensure your vacation goes as smoothly as possible.

There’s plenty of space for me-time. Each cabin has its own private bathroom. Communal areas are open, airy, and spacious, so you can relax without feeling claustrophobic.

You’ll never be in the dark. We’ll answer any and all questions you may have. And if you’re not sure what to do for your trip, we can suggest our favorite bars, stops, and hidden gems to make your vacation spectacular.

It’s your trip and yours alone. The trip is designed to accommodate your specific needs, including your party’s food preferences, allergies, activity level, sleep schedule, and much more.

We’re flexible. Because we’re owner-operated, you don’t have to wait days or more if you want to change your plans. We can make adjustments right away if something comes up or you want to explore something new.

Meet the S/Y Barefoot Cowboy, Your Home Away from Home

2015 Leopard 58

Nothing compares to cruising the sea aboard the Leopard 58. Barefoot Cowboy has a spacious, split-level floor plan. On the main deck you will find two cabins opening to a forward cockpit. Three cabins below, all with private en-suite baths. All cabins are air-conditioned.


Inside you will discover a well appointed galley. Meals can be enjoyed inside with wrap around seating for 10. The yacht also comes complete with a 46” flat screen TV/DVD player, onboard WiFi, Apple TV, CD stereo with MP3 connection.

Venture up to the enormous fly bridge and captain from the helm station with a 360-degree vantage point. The fly bridge includes stylish lounge seating with an electric grill, wet bar and refrigerator. This is the place to gather and enjoy cocktails with friends. The fly bridge is also wired for sound. Feel free to dance!


The best place for al fresco dining is on our aft deck. Barefoot Cowboy has a beautiful teak table for 10 and a view of the islands you will never forget.


Barefoot Cowboy is the perfect escape for large groups up to 10 guest.


Boat Features:

  • 2021 15’ AB tender with 50 hp Yamaha out board engine

  • 2-Standup Paddle Boards

  • Sub-Wing

  • Towable Tube aka Big Mable

  • 2-Person Inflatable Kayak

  • Snorkeling Gear

  • Floating Mats

  • Go-Pro Camera


  • Insta 360 Camera

  • Fishing Gear

  • Floating Dock

  • Swimming Platform

  • Underwater Lights

  • Games

  • Over 300 Movies

  • Deep Sea Fishing (By rendezvous)

  • Scuba Diving ( By rendezvous)

Meet Your Crew

Roy Pat headshot

Roy Pat Rucker

Captain

100 Ton Master with Sailing Endorsement

STCW Certified

Advanced and Rescue Diver

Captain Roy Pat Rucker has helped dozens of clients experience unforgettable dream vacations since 2013. He has spent over 4 years sailing around the Virgin Islands and is a certified advanced diver. He’s a Texas-born-and-raised cowboy who worked on ranches and rodeoed in his youth.

He recently retired from BP after 30 years of service, where he held many roles including mechanic, lead tech, maintenance team leader, fireteam leader, and maintenance planner working on offshore platforms in the Gulf of Mexico and the Caspian sea off the coast of Azerbaijan.

In 2017, he lost his Three Moons Charter yacht to Hurricane Maria in Puerto Rico. He was devastated at seeing the damage the island had taken and all his hard work in utter desolation. He did everything right, but in the end, he lost his dream and his crew lost their jobs.

Through the ordeal, however, he ended up getting married and realized how much he had loved his time on S/Y Three Moons. He and his wife, Natalie decided to get a catamaran together and start over.

Natalie headshot

Natalie Rucker

Chef, Boss, & Happy-Go-Lucky Lady!

STCW Certified

Natalie’s background is in the optical world, where she spent 28 years as a certified optician. She loves working with people and customizing their experience. Customer service is her forte!

Natalie will tell you she has the best job in the entire world. She gets to help make sure you eat delicious food, drink the best drinks, and have the time of your life! And as an added bonus, she can adjust your sunglasses if you sit on them.

Natalie’s favorite destination is Dinghy's on Water Island for Sunday Funday. She also loves Hull Bay for the local beach vibe. For drinks, she’s a sucker for Diet Coke & Cruzan Rum.

Pete photo

Pete

Second Mate/ Security Officer

You won’t find a better Second Mate than this handsome, well-mannered Miniature Wirehaired Dachshund. As a mature 4-year-old, Pete is dedicated to keeping the crew and all aboard the Barefoot Cowboy in good spirits. He’s laid back, enjoys chasing reflections, and acts as Captain Roy’s shadow when off-duty.


Pete also specializes in security detail. He ensures that any dropped food on deck is cleaned up ASAP.

Meet Your Crew

Roy Pat headshot

Roy Pat Rucker

Captain

100 Ton Master with Sailing Endorsement STCW Certified Advanced and Rescue Diver

Captain Roy Pat Rucker has helped dozens of clients experience unforgettable dream vacations since 2013. He has spent over 4 years sailing around the Virgin Islands and is a certified advanced diver. He’s a Texas-born-and-raised cowboy who worked on ranches and rodeoed in his youth.

He recently retired from BP after 30 years of service, where he held many roles including mechanic, lead tech, maintenance team leader, fireteam leader, and maintenance planner working on offshore platforms in the Gulf of Mexico and the Caspian sea off the coast of Azerbaijan.

In 2017, he lost his Three Moons Charter yacht to Hurricane Maria in Puerto Rico. He was devastated at seeing the damage the island had taken and all his hard work in utter desolation. He did everything right, but in the end, he lost his dream and his crew lost their jobs.

Through the ordeal, however, he ended up getting married and realized how much he had loved his time on S/Y Three Moons. He and his wife, Natalie decided to get a catamaran together and start over.

Natalie headshot

Natalie Rucker

Chef, Boss, & Happy-Go-Lucky Lady!

STCW Certified

Natalie’s background is in the optical world, where she spent 28 years as a certified optician. She loves working with people and customizing their experience. Customer service is her forte!

Natalie will tell you she has the best job in the entire world. She gets to help make sure you eat delicious food, drink the best drinks, and have the time of your life! And as an added bonus, she can adjust your sunglasses if you sit on them.

Natallie’s favorite destination is the Baths in Virgin Gorda. There is nothing more beautiful than this amazing, God made rock formation. For drinks, she’s a sucker for Diet Coke & Cruzan Rum and Margaritas!

2022 will be her first season on Barefoot Cowboy and she is thrilled.

Pete photo

Pete

Second Mate/ Security Officer

You won’t find a better Second Mate than this handsome, well-mannered Miniature Wirehair Dachshund. As a mature 4-year-old, Pete is dedicated to keeping the crew and all aboard the Barefoot Cowboy in good spirits. He’s laid back, enjoys chasing reflections, and acts as Captain Roy’s shadow when off-duty.


Pete also specializes in security detail. He ensures that any dropped food on deck is cleaned up ASAP.

Don’t Miss Out on the Vacation of a Lifetime

Life is too short to waste on overpriced cruise ships with predetermined activities, tight schedules, and crowded decks. Reach out to Barefoot Cowboy today and plan the trip you’ve always dreamed of.

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GO BAREFOOT!

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