BAREFOOT COWBOY is a Leopard 58 built for lively Caribbean charters, offering generous split-level living and plenty of space for groups to spread out. Two main-deck queen cabins open directly to the forward cockpit for easy access, while 3 additional cabins below provide added privacy. The enormous flybridge is a standout, with panoramic 360° views, helm-side lounge seating, a wet bar, refrigerator, electric grill, and sound throughout for relaxed afternoons or sunset cocktails.
Accommodating up to 10 guests, BAREFOOT COWBOY offers 4 queen cabins and 1 twin cabin that can convert to a king upon request. Each air-conditioned cabin includes a private ensuite head and shower. A teak dining table for 10 sets the scene for memorable alfresco meals, while Wi-Fi, Apple TV, a 46” Samsung LED TV, Bose surround sound, and a Bluetooth-enabled Fusion entertainment system keep the onboard experience comfortable and connected. Spacious, social, and ready for fun, BAREFOOT COWBOY brings the energy.
Photo Gallery
Videos/VR
Yacht Video
Watersports & Toys
Dinghy
Fishing Gear2 Casting rods
Fishing Permit #BVI Permit in Process
Floating Mats
Kayaks - 2 Man
Snorkel Gear
Stand-up Paddle Boards
Tube
Water Skis Kids
Other Toys
9 Person Dinghy With 50HP 1 Subwing 1 2-Person Kayak 2 Stand Up Paddle Boards 1 Kids Water Ski Towable Tube 2 Floating Mats Snorkel Gear Fishing Gear Underwater Camera 2 Floating Chairs Megachill Foam Noodles Dinghy Boarding Ladder Beach Games
Scuba Diving
Scuba Availability
Rendezvous Not Included
Amenities
BBQ
Board Games
Books
CDs/Music
Deck Shower
Dine In
DVDs/Movies
Generator
Guest SmokesSugar Scoops only
Hair Dryers
1
Hammock
Ice Maker
iPod/MP3 Hookups
Onboard InternetStarlink
Salon Stereo/Music
Salon TV/DVD
Videos
Other Entertainment
Eisenglass Weather Protection
Parents must bring life jackets for kids
Green Initiatives
Drinking Water Tested for Purity
Yes
Re-usable Water Bottles
Yes
Yacht Crew
2 Total Crew
About the Crew
Captain Roy Pat Rucker, Chef Natalie Rucker, and First Mate Pete bring a fun, welcoming, and deeply personal spirit to every charter aboard BAREFOOT COWBOY. Roy’s years of Virgin Islands sailing and technical experience pair with Natalie’s warm hospitality and guest-focused service, while Pete keeps morale high and ensures no snack goes unattended.
Click each crew profile to learn more about their background, experience, and personal story.
Meet the Crew
Roy Rucker
Captain
Nationality: American
Languages: English
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Natalie Rucker
Chef/First Mate
Nationality: American
Languages: English
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Pete
Onboard Friendly Dog
Nationality: Miniature Wirehaired Dachshund
Languages: Woof Woof
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Yacht Menu
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Culinary Experience
Freshly prepared cuisine featuring relaxed breakfasts, flavorful midday favorites, plated dinners, sweet finishes, and cocktails crafted for life aboard. Sample menu selections are listed below and ma...
Sample Menus
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Dinner
Main Course Features
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Dinner
Hors d’Oeuvres Aboard
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Dinner
Hors d’Oeuvres Aboard
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Lunch
Midday Favorites
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Sweets
Sweet Finishes
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Dinner
Main Course Features
Guest Reviews
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April 2025
Fantastic. I noted to Capt. Roy Pat and Natalie about halfway through the trip that I thought we were lucky and so grateful to have gotten THEM as our crew. As we progressed through the trip and saw the other boats and people with their crew out at restaurants, I knew we had won the lottery! Capt. Roy Pat, Natalie and Jenna were wonderful, totally our speed, and we really enjoyed getting to know them and hear their stories!!
Everything from ID’ing fish to answering questions about the various areas we visited to recipe questions…. There was nothing they didn’t know! We truly enjoyed getting to know them and we trusted everything they had to say, from restaurant options down to changing course because of the rough seas and winds.
We wanted for nothing all week. Emily and I felt a tad strange not helping with cleaning up… and it felt a little weird to be catered to when we are all used to doing everything on our own. That isn’t necessarily a negative!! Ha! Just took some getting used to!!!
At no time did we feel like we were not in good hands.
WE LOVED NATALIE’S FOOD. I think we would have done ALL meals on the boat had that been an option. I loved her food so much, that I looked through her cookbook and took pics of recipes!!! We told her we ate a LOT, and she nailed it!!
We did not want to leave and we are already trying to figure out when we could come back! Doing this trip with family was amazing. The kids get along so well. No one ever got bored. No snippy bickering. We truly got to relax and decompress from work, school, and sports. It was the perfect vacation!!!
Our most memorable highlight was the “Highs and Lows” discussion at the end of the day with everyone. What a special way to cement the memories made that day and hear what everyone else thought about their day!! We are grateful to Capt. Roy Pat and Natalie for introducing us to that little end-of-day discussion idea!!! Of course, the food, snorkeling, diving, laughs, island hopping, sunburns, sleeping in the beanbags, reading in the shade, fun conversations, etc…. Soooo many things made the highlight reel in our minds!!
Natalie
April 2025
We had a fabulous vacation sailing through the BVI's on Barefoot Cowboy! Many thanks to you for linking us up with Captain Roy Pat & Natalie. We appreciate all the information and communication you provided us with leading up to our trip. We would absolutely give the 9 items you listed a 10 out of 10. Roy Pat, Natalie & Jenna were so kind, helpful, knowledgeable and professional throughout the entire trip. They knew we were an active group and did a great job of finding fun spots for us to snorkel & explore. The meals they prepared were delicious and always crowd pleasers! Highlights for us were definitely seeing all the awesome sea life on our snorkeling adventures, exploring The Baths on Virgin Gorda, and just spending quality time together as a family. Thanks again for helping us organize an unforgettable vacation!
Take care,
Emily & Justin
April 2025
We just returned from a glorious 7 days aboard the Barefoot Cowboy, and we're already dreaming about when we can return. To say we were spoiled would be an understatement!
Captain Roy Pat was phenomenal-navigating us to all the best spots throughout the Virgin Islands with such expertise - every day felt like a new adventure. Chef Natalie absolutely blew us away with every single meal. You could truly taste the heart and soul she put into her cooking. My personal favorites? The perfectly cooked filet mignon for dinner and the fresh, flavorful chicken avocado salad for lunch-both were out of this world!
And Pete... what can I say? He's the sweetest little pirate out there and totally stole our hearts.
This was our first trip to the Virgin Islands, and we couldn't have asked for a better introduction. We loved every stop-Willy T's, Cooper Island, everything about Jost Van Dyke, and the beauty of St. John. Every day brought something new and unforgettable.
We're already counting down the days until we can return for more sailing, more sunshine, and more amazing memories!
Lori
March 2025
We loved the front trampolines and all the extras on the yacht! The paddle boards and the mega chill were a huge hit. There was nothing we missed. They had everything!! One tiny down side was the bathroom sizes but you can live with it for a week or two in paradise. We loved the crew!! The yacht pup was the cutest extra!
This was an absolute trip of a lifetime for us!! We loved every single second of our time on the boat and on the islands!!
Mandie
June 2024
We sailed with Roy Pat, Natalie and pirate Pete June 2024. It was without a doubt the most amazing vacation. Words can't describe the hospitality that was received and the friendships that were made. I highly recommend sailing with Barefoot Cowboy, simply the best!!
Kathy
January 2025
This was the best family vacation we ever had! Roy and Natalie were incredible hosts! From accommodations to the food to the fun! Highly recommend.
Clare
January 2023
Beautiful boat with an outstanding crew! They know all of the best spots to visit around the VI, and all of the tips and tricks to make sure you get the most out of your vacation. It’s like having your own local guides as your hosts. Can’t wait to go back. This is a trip that you won’t soon forget!
December 2022
It’s was all we dreamed it would be…Food was delicious and beautifully served…The staff exceptional, will go every chance we get!!!
December 2023
To say this is a once in a lifetime vacation sounds cliche but its just amazing. The crew, the food, the islands. Everything is top notch. Can’t wait to set sail again. This is so much more than a “cruise” could ever offer.
December 2022
This catamaran and the crew are first class. The crew is very attentive and accommodating. We can’t wait to sail again with Captain Roy Pat and Chef Natalie!
Base Port • Yacht Haven Grande (YHG) – St. Thomas, USVI • Additional pick-up/drop-off available at American Yacht Harbor (AYH), St. Thomas • BVI ports available on request (Contact us for details)
Yacht Status & Operations • Based in St. Thomas, USVI
• STT-Foreign Based Unlimited • USVI pick-up/drop-off preferred • BVI pick-ups/drop-offs accepted with advance approval
Customs Fees & Cruising Permits • Included
Rates & Terms Minimum charter nights • 5-night minimum • Shorter charters considered on request
Short-Term Charter Rate Calculations • 6 nights = weekly rate ÷ 7 × 6 • 5 nights or less = weekly rate ÷ 6 × number of nights
Sleep Aboard Option Enjoy a relaxed evening onboard before your charter begins. • Now available for free • Boarding available after 4:00 PM • Includes snacks, welcome cocktails & continental breakfast • Dinner ashore at guest expense • Excludes Christmas & New Year’s weeks
Dining Options – The number of meals listed are based on a 7 night charter Full-Board Plan- Great for guests who want a fully onboard culinary experience • 7 breakfasts, 7 lunches & 7 dinners onboard • Standard plan included in your charter rate
Half-Board Plan – Ideal for guests who enjoy dining ashore • 7 breakfasts, 4 lunches & 3 dinners onboard • 3 lunches & 4 dinners ashore (guest expense) • $150 per person discount
Local Fare Meal Plan – A taste of Caribbean cuisine • 7 breakfasts, 5 lunches & 6 dinners onboard • 2 lunches & 1 dinner ashore (guest expense) • $75 per person discount
Holiday Rates 2026 / 2027 Season Holiday season pricing is full-board only, 7 nights
Christmas Week • $40,000 | 2–10 guests • Must end on or before December 26
New Year’s Week • $43,000 | 2–10 guests • May not start prior to December 27
Important Notes • Charter waiver required in addition to standard contract • Please inquire for BVI port availability due to annual limit
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