Barefoot Cowboy Description
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 dinning is on our aft deck. Barefoot Cowboy has a beautiful teak table for 10 and a view of the islands you will never forget. She is the perfect escape for large groups up to 10 guests.
Cruising Area of Barefoot Cowboy
Accommodations
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
Specification
Water Sports
2 Stand Up Paddle Boards
1 Bote 2 Person Inflatable Kayak
2 Bote Floating Chairs
Megachill
Noodles
Underwater Camera
Snorkeling Gear
Tubes
1 Subwing
2 Fishing Rods
Onshore Games.
Dinghy Boarding Ladder
Scuba Diving 
Entertainment
Eisenglass Weather Protection
Starlink internet
Cuisine
Green Initiatives
Barefoot Cowboy Crew Profile
Captain
Chef / First Mate
Captain Roy Pat Rucker
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.
Chef Natalie Rucker
Natalie’s background is in the optical world, where she spent 29 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 Fundays and live music. She also loves Hull Bay for is quiet local vibe. For drinks, she’s a sucker for Diet Coke & Cruzan Rum and Margaritas!
First Mate/ Security Officer/ Cuddle Buddy ´Pete´
You won’t find a better First Mate than this handsome, well-mannered Miniature Wirehaired Dachshund. As a mature 5-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, riding in the dinghy, long walks on the beach, swimming, loves naps and acts as Captain Roy’s shadow when off-duty.
He has made over 200 friends in his first year of duty! He enjoys the dock hands stopping by to say hello and bring him treats.
Pete also specializes in security detail. He ensures that any dropped food on deck is cleaned up ASAP.
Barefoot Cowboy Calendar
AvailableBookedHold (can be challenged)Unavailable| May 2025 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
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| Jun 2025 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | |
| Jul 2025 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
| Aug 2025 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
| Sep 2025 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | |
| Oct 2025 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
| Nov 2025 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | |
| Dec 2025 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
| Jan 2026 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
| Feb 2026 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | |||
| Mar 2026 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
| Apr 2026 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | |
| May 2026 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
| Jun 2026 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | |
| Jul 2026 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
| Aug 2026 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
| Sep 2026 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | |
| Oct 2026 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 29 | 30 | 31 |
Barefoot Cowboy Reservations & Port Locations
| Start Date | End Date | Details (Holds can be challenged) |
|---|---|---|
| Apr 30, 2025 | May 07, 2025 | Booked: British Virgin Islands* to British Virgin Islands* |
| May 10, 2025 | May 17, 2025 | Booked: Tortola, TBD to St Thomas, USVI* |
| Jun 04, 2025 | Jun 09, 2025 | Booked: Tortola, Village Cay, BVI to Yacht Haven Grand |
| Jun 11, 2025 | Jun 16, 2025 | Booked: Tortola, Village Cay, BVI to St Thomas, USVI* |
| Jun 28, 2025 | Jul 05, 2025 | Booked: British Virgin Islands* to British Virgin Islands* |
| Jul 23, 2025 | Jul 30, 2025 | Booked: St Thomas, USVI* to St Thomas, USVI* |
| Aug 01, 2025 | Oct 31, 2025 | Unavailable: Unavailable to Unavailable |
| Nov 02, 2025 | Nov 08, 2025 | Booked: Yacht Haven Grand to Yacht Haven Grand |
| Nov 23, 2025 | Nov 29, 2025 | Booked: British Virgin Islands* to British Virgin Islands* |
| Dec 28, 2025 | Jan 03, 2026 | Booked: British Virgin Islands* to British Virgin Islands* |
| Jan 18, 2026 | Jan 25, 2026 | Booked: British Virgin Islands* to British Virgin Islands* |
| Jan 29, 2026 | Feb 05, 2026 | Booked: British Virgin Islands* to British Virgin Islands* |
| Feb 14, 2026 | Feb 21, 2026 | Booked: British Virgin Islands* to British Virgin Islands* |
| Mar 04, 2026 | Mar 12, 2026 | Booked: British Virgin Islands* to British Virgin Islands* |
| May 01, 2026 | May 09, 2026 | Unavailable: Unavailable, Crew Holiday to Unavailable, Crew Holiday |
| May 29, 2026 | Jun 06, 2026 | Booked: Yacht Haven Grand to Yacht Haven Grand |
Barefoot Cowboy Rates / week
The prices shown are for the entire yacht for a week-long (7 nights) charter. Inquire for lowest rate.Low price: $28,700
High price: $36,000
| Season | 2 Pax | 3 Pax | 4 Pax | 5 Pax | 6 Pax | 7 Pax | 8 Pax | 9 Pax | 10 Pax |
|---|---|---|---|---|---|---|---|---|---|
| 2025 Summer | $32,000 | $32,500 | $33,000 | $33,500 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 |
| 2025/26 Winter | $32,000 | $32,500 | $33,000 | $33,500 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 |
| 2026 Summer | $32,000 | $32,500 | $33,000 | $33,500 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 |
Yacht terms: All Inclusive
An all-inclusive charter covers all provisioning and running expenses. This includes a captain and crew that is fully trained and committed to your safety and enjoyment of your trip. A chef will provide the kind of exceptional, personalized meal preparation that you would expect of a five-star restaurant. The listed rate may not include all local taxes, cruising permits, premium beverages and scuba activities. Inquire for more information.
ADDITIONAL RATE DETAILS
CRUISING GROUNDS: British Virgin Islands
Pick Up/Drop Off: Tortola; inquire for other locations
Yacht: BVI-Based
Crew: Annual Work Permits
BVI Customs & Cruising Permit Fees: Included
MINIMUM NIGHTS: 5, Inquire for less.
For 6 night charters, divide weekly rate by 7 nights X 6 nights. For 5 nights or less, divide weekly rate by 6 nights X number of nights.
HALF-BOARD OPTION: Includes 7 breakfasts, 4 lunches & 3 dinners, happy hour canapes, standard ships bar and snacks. Other meals ashore at client expense.
2@$28,700 | 3@$29,050 | 4@$29,400 | 5@$29,750 | 6@$30,100 | 7@$30,450 | 8@$30,800 | 9@$31,150 | 10@$31,500
LOCAL FARE OPTION: Includes 7 breakfasts, 5 lunches & 6 dinners, happy hour canapes, standard ships bar and snacks. Other meals ashore at client expense.
2@$28,850 | 3@$29,275 | 4@$29,700 | 5@$30,125 | 6@$30,550 | 7@$30,975 | 8@$31,400 | 9@$31,825 | 10@$32,250
SLEEP ABOARD: ** Now FREE! **
Includes boarding after 4pm, snacks, welcome cocktails & continental breakfast. Dinner ashore is additional. Select option upon booking. EXCLUDES: Christmas and New Year´s weeks.
25/26 HOLIDAYS: 7 night minimum. Full board.
CHRISTMAS: $40,000 Must end on or before 12/27
NEW YEARS: $43,000 May not start prior to 12/28
Barefoot Cowboy Guest Reviews
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!
