BAREFOOT COWBOY is a Leopard 58 built for big-group Caribbean fun and split-level space. Two main-deck Queen cabins open to the forward cockpit—ideal for easy access—while three cabins sit below for added privacy. Sleeping up to 10, she offers 5 air-conditioned cabins: 4 Queens plus 1 Twin (converts to a King), each with a private ensuite head and shower. Standout feature: the enormous flybridge with 360° views, helm lounge seating, wet bar, fridge, and electric grill—plus sound wiring for cocktails and a little dancing. Gather aft around the teak table for 10 for unforgettable al fresco meals. WiFi + Apple TV keep you connected—if you want to be. Bring your people—BAREFOOT COWBOY brings the vibe.
Yacht Description
“A 58ft Leopard from 2015.”
Broker Review
Onboard visit
Barefoot Cowboy comes with a third crew member — Pirate Pete, the ship's resident terrier. Captain Roy and Chef Natalie, a warm and easygoing couple, bring a refreshingly straightforward all-American vibe: cold beers, meat-and-cheese tapas, and every kind of floating lounge chair you could want. It's a genuinely relaxed, homey charter with personal touches throughout.
Klara Jakobsen
Broker Assistant
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Captain Only: This yacht is available for captain-only charter.
Specifications
- Length overall
- 58ft / 17 m
- Beam
- 8.23m
- Draft
- 1.74m
- Builder
- Leopard
- Year built
- 2015
- Refit
- 2023
- Type
- Sailing Catamaran
- Cruising speed
- 10 knots
- Top speed
- 20 knots
- Engines
- 2, 110hp Yanmar engins, 1 22kw Norhtern Lights Generator
- Generator
- 1 22kw Norhtern Lights Generat
- Guests
- 10
- Cabins
- 5
- Crew
- 2
Charter Price
From $33,000 per week, all-inclusive.
All-Inclusive arrangement — expenses covered.
Charter days
Base price
APA
Total estimate
Note
14 days
$66,000
Included
$66,000
Discounts outside main season common
7 days
$33,000
Included
$33,000
Standard charter rate
3 days
$16,500
Included
$16,500
Estimate for a short charter
All prices generated as a guide. Availability subject to confirmation. Gratuity discretionary, typically 5%–25% of the base price.
This yacht charters on all-inclusive terms — fuel, food, drinks and standard running expenses are covered in the charter price, so no APA deposit is added.
- Total guests
- 10
- Total cabins
- 5
- Queen cabins
- 4
- Twin cabins
- 1
- Electric heads
- 5
- Showers
- 5
- Basins
- 5
- A/C
- Full
- A/C at night
- Yes
5 staterooms for 10 guests.
4
Queen cabins
1
Twin cabins
4 Queens and 1 Twin. The twin cabin converts to a King upon request.
Electronics: RayMarine chart plotter, depth, wind and auto-pilot VHF Solon electronics include. 46" Samsung LED TV, Bose Surround sound system, Fusion entertainment system with blue tooth and wifi.
2023/2024 Refit:
2023-
Electric grill on the flybridge replaced.
All window blinds in state rooms replaced.
Flybridge enclosure replaced.
VHF radio replaced.
Ice Maker installed.
Fridge on the flybridge replaced.
6- 210 ah Lifeline AGM house batteries replaced..
Northern Lights 20kw generator replaced.
2024-
Water Maker replaced with Sea Recovery Aqua Matic.
Installed 6- 310w Solar Panels,Charge Controllers, GX Touch 70, Cerbo Gx and 500A/50mV Smartshunt.
New Generator
New AC unit/chilled water system
- Captain
- Roy Pat Rucker
- Nationality
- USA
- License
- 100T
- Crew size
- 2
Roy Rucker
Captain
<p><strong>Captain Roy Rucker</strong><br>Captain Roy Pat Rucker has been helping guests enjoy unforgettable charter vacations since 2013. A Texas-born-and-raised cowboy, he grew up working on ranches and participating in rodeos before building a life centered around the sea.<br><br>Roy has spent more than four years sailing throughout the Virgin Islands and is also a certified advanced diver. Before fully embracing charter life, he spent 30 years with BP, working in a variety of technical and leadership roles including mechanic, lead technician, maintenance team leader, fireteam leader, and maintenance planner. His career took him aboard offshore platforms in the Gulf of Mexico and the Caspian Sea off the coast of Azerbaijan.<br><br>In 2017, Roy lost his charter yacht, THREE MOONS, during Hurricane Maria in Puerto Rico. The loss was devastating, but it also reminded him how deeply he loved life on the water and sharing it with others.</p><p>Determined to begin again, Roy and his wife, Natalie, purchased a catamaran together and returned to chartering. Today, he brings technical knowledge, calm leadership, and genuine enthusiasm to every trip, helping guests experience the beauty, adventure, and relaxed rhythm of the Virgin Islands.</p><p> </p><p> </p>
Natalie Rucker
Chef/First Mate
<p><strong>Chef Natalie Rucker</strong><br>Chef Natalie Rucker spent 29 years working as a certified optician, where she developed a strong talent for customer service and creating personalized experiences. That same thoughtful, people-focused approach now shapes the way she cares for guests onboard.<br><br>Natalie loves helping guests eat well, enjoy great drinks, and make the most of every moment on charter. Her warm personality and natural hospitality create an easygoing atmosphere where guests feel comfortable, welcomed, and well looked after.<br><br>She enjoys tailoring the experience to each group, from meals and cocktails to favorite island stops and relaxed afternoons on the water. And, as an added bonus, she can even adjust your sunglasses if you happen to sit on them.<br><br>Some of Natalie’s favorite local spots include Dinghy’s on Water Island for Sunday Fundays and live music, and Hull Bay for its quiet, local feel. Her drink of choice is Diet Coke with Cruzan Rum, though she is always happy to enjoy a good margarita as well.</p><p> </p><p> </p>
-
Pete
- Salon stereo
- Yes
- Salon TV
- Yes
- Multimedia
- Yes
- Nude charters
- On inquiry
- Books
- Yes
- Crew pets
- Yes
- Pet type
- Very calm and friendly small dog, Pete
- Dine-in capacity
- 10
- Watermaker
- Yes
- Ice maker
- Yes
- DVDs
- Yes
- CDs
- Yes
- Board games
- Yes
- Special diets
- Yes
- BBQ
- Yes
- Gay charters
- On inquiry
- Hairdryers
- Yes
- Smoking allowed
- Sugar Scoops only
- Children welcome
- Yes
- Min. child age
- Any Age
- Generator
- 1 22kw Norhtern Lights Generat
- Voltages
- 220/120v
- Hammock
- Yes
- Internet
- Onboard WIFI
- Dinghy size
- AB
- 2-pax kayaks
- 1
- Dinghy HP
- 50
- Floating mats
- 2
- Dinghy pax
- 9
- Water skis (kids)
- Yes
- Snorkel gear
- Yes
- Paddleboard
- 2
Onboard Entertainment
Eisenglass Weather Protection Starlink internet
Diving
Yacht offers Rendezvous Diving only
Fishing
Sustainability
Registry & Permits
- Flag
- US
- Homeport
- STT-Foreign Based Unlimited
- License
- 1
- Permit
- 1
- Insurance
- Edward William
Charter Reviews
BAREFOOT COWBOY
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
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
BAREFOOT COWBOY
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
Take care,
Emily & Justin
BAREFOOT COWBOY
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
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
BAREFOOT COWBOY
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
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
BAREFOOT COWBOY
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
Kathy
BAREFOOT COWBOY
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
Clare
BAREFOOT COWBOY
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!
BAREFOOT COWBOY
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!!!
BAREFOOT COWBOY
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.
BAREFOOT COWBOY
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!
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