- Amenities Details
- 7-Night Rates
- Availability
- Specifications
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.
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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
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Rendezvous Not Included
- 2 Guests: $32,000
- 3 Guests: $32,500
- 4 Guests: $33,000
- 5 Guests: $33,500
- 6 Guests: $34,000
- 7 Guests: $34,500
- 8 Guests: $35,000
- 9 Guests: $35,500
- 10 Guests: $36,000
- 2 Guests: $33,000
- 3 Guests: $33,500
- 4 Guests: $34,000
- 5 Guests: $34,500
- 6 Guests: $35,000
- 7 Guests: $35,500
- 8 Guests: $36,000
- 9 Guests: $36,500
- 10 Guests: $37,000
- 2 Guests: $33,000
- 3 Guests: $33,500
- 4 Guests: $34,000
- 5 Guests: $34,500
- 6 Guests: $35,000
- 7 Guests: $35,500
- 8 Guests: $36,000
- 9 Guests: $36,500
- 10 Guests: $37,000
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• 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
Check Charter Availability by Month
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Yacht layout
Specifications
Amenities
Water Sports
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
- Year Built 2015
- Length 58 ft.
- Designer Leopard
- Cabins 5
- Maximum Guests 10
- Starting From $27,200
*2 Guests, 5 Nights with Half-Board Meal Package
Got a Question? We’ve Got Answers.
Meet our Crew
Captain Roy Rucker
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.
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.
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.
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.
Chef Natalie Rucker
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.
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.
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.
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.
3rd Mate Pete
Pete is a handsome, well-mannered Miniature Wirehaired Dachshund and a much-loved member of the crew aboard BAREFOOT COWBOY. At five years old, he takes his duties seriously, especially when it comes to keeping everyone onboard smiling.
Laid-back and affectionate, Pete enjoys riding in the dinghy, taking long walks on the beach, swimming, chasing reflections, and fitting in plenty of naps between activities. When off duty, he can often be found close beside Captain Roy.
Pete has already made more than 200 friends during his first year of service and is especially popular with dockhands, who frequently stop by to say hello and bring him treats.
He also takes his role as Security Officer very seriously. Any food dropped on deck is inspected and removed immediately, helping keep BAREFOOT COWBOY clean, secure, and snack-free at all times.
Onboard Dining
Guest Testimonials
