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

Pref. Pick-upYHG, St Thomas
Other Pick-upRed Hook, St Thomas
Summer PortSt. Thomas, USVI
Winter PortSt. Thomas, USVI
Summer OperationsCaribbean Virgin Islands
Winter OperationsCaribbean Virgin Islands


Wash Basins5
TP in Heads-
Electric Heads5
Accommodation Details
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.


Length58 Feet
Beam27 Feet
Draft5.7 Feet
A/C NightYes
Guest SmokeSugar Scoops only
Children AllowedYes
Min Child Age5
Water MakerYes
Ice MakerYes
Internet AccessOnboard WIFI
Generator1 22kw Norhtern Lights Generat
Max Speed20
Cruising Speed10
Turnaround48 hrs preferred, Inquire for
Engines2, 110hp Yanmar engins, 1 22kw Norhtern Lights Generator

Water Sports

Dinghy (Feet)AB
Dinghy Hp50
Dinghy Pax9
Kids WaterskisYes
Snorkel GearYes
Floating Mats2
Standup Paddle2
Fishing GearYes
Gear Type2 Casting
Fishing Rods2
Other Toys
Swim plarform
Beach games-Bochie ball and Bote Corn hole (bag toss)
Boate Hang Out floating 360 w/ bar
Bote floating chairs
underwater camera
boarding ladder on dinghy
Twin beds convert to King size bed
Starlink internet

Scuba Diving Scuba Diving Symbol

ScubaYacht offers Rendezvous Diving only
Air CompressorNot Onboard


Salon Tv/DvdYes
Salon StereoYes
iPod/Device HookupsYes
Board GamesYes
Other Entertainment
Eisenglass Weather Protection


Special DietsInq

Green Initiatives

Make Purified Drinking WaterYes
Re-Usable Water BottlesYes

Barefoot Cowboy Crew Profile

Crew Number2
Crew SmokeNo
Crew PetsYes
Crew Pet TypeVery calm and friendly small dog, Pete
CaptainRoy Pat Rucker
Chef / First Mate
Chef / First MateNatalie Rucker

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

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Barefoot Cowboy Reservations & Port Locations

Start DateEnd DateDetails (Holds can be challenged)
Jul 17, 2024Jul 24, 2024Booked: St Thomas, USVI* to St Thomas, USVI*
Aug 01, 2024Oct 31, 2024Unavailable: Unavailable to Unavailable
Nov 25, 2024Dec 01, 2024Booked: St Thomas, USVI* to St Thomas, USVI*
Dec 08, 2024Dec 15, 2024Booked: St Thomas, USVI* to St Thomas, USVI*
Dec 17, 2024Dec 24, 2024Booked: Tortola, TBD to Tortola, TBD
Dec 26, 2024Jan 02, 2025Booked: Yacht Haven Grand to Yacht Haven Grand
Jan 27, 2025Feb 01, 2025Booked: Yacht Haven Grand to Yacht Haven Grand
Feb 04, 2025Feb 11, 2025Booked: St Thomas, USVI* to St Thomas, USVI*
Mar 06, 2025Mar 13, 2025Booked: Yacht Haven Grand to Yacht Haven Grand
Apr 05, 2025Apr 12, 2025Booked: Tortola, TBD to Tortola, TBD
Aug 01, 2025Oct 31, 2025Unavailable: Unavailable to Unavailable
Nov 02, 2025Nov 08, 2025Booked: 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: $31,700
(normal rate)
High price: $36,000
(normal rate)

Barefoot Cowboy Special Offer!
Discount: 10%!
Offer: Barefoot Cowboy offers a 10% discount for charters booked & completed by July 31th, 2024. Cannot be in conjunction with any other specials.
Old price: $31,700 - $36,000 / week
New price: $28,530 - $32,400 / week (Save: $3,170 - $3,600 / week)
Minimum nights: 5
Travel before: Jul/31/2024

Season2 Pax3 Pax4 Pax5 Pax6 Pax7 Pax8 Pax9 Pax10 Pax
2024 Summer$32,000$32,500$33,000$33,500$34,000$34,500$35,000$35,500$36,000
2024/25 Winter$32,000$32,500$33,000$33,500$34,000$34,500$35,000$35,500$36,000
2025 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.


LESS THAN 7 NIGHT CHARTERS: For 6 nights divide by 7N X 6N. For less than 6 nights, divide by 6N X number of nights.

BVI FEE: Customs/Immigration and Cruising permit fees included in rate. This vessel is legal to conduct charters in the BVI.

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@$31,700 | 3@$32,050 | 4@$32,400 | 5@$32,750 | 6@$33,100 | 7@$33,450 | 8@$33,800 | 9@$34,150 | 10@$34,500

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@$31,850 | 3@$32,275 | 4@$32,700 | 5@$33,125 | 6@$33,550 | 7@$33,975 | 8@$34,400 | 9@$34,825 | 10@$35,250

SLEEP ABOARD: Available for half of the daily rate. Includes boarding after 4pm, snacks, welcome cocktails & continental breakfast. Dinner ashore is additional. Select option upon booking. EXCLUDES: Christmas and New Year´s weeks.

CHRISTMAS/NEW YEARS: 7 night minimum.
CHRISTMAS 2024: *Already Booked*
NEW YEARS ´24/25: *Already Booked*

Barefoot Cowboy Guest Reviews

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!