MORE INFORMATION

Summer location
Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)

Winter location
Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)

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.

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

Price Details
Cruising Area
• Virgin Islands (USVI & BVI)

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
• 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

Inclusive

BAREFOOT COWBOY

Beam: 27

Draft: 5.7

Max Speed: 20

Total Cabins: 5

King Cabins: 0

Queen Cabins: 4

Single Cabins: 0

Double Cabins: 0

Twin Cabins: 1

Pullman Cabins: 0

Helipad: No

Jacuzzi: No

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

Entertainment:
Eisenglass Weather Protection
Starlink internet

Communication:
Parents must bring life jackets for kids.

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.