BAREFOOTCOWBOY

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.

• BBQ
• Board Games
• Books
• CDs
• Deck Shower
• Dining
• DVDs
• Generator: 1 22kw Norhtern Lights Generat
• Smoking Allowed: Sugar Scoops only
• Hair Dryer
• Hammock
• Ice Maker
• iPod/MP3
• Internet/WiFi: Starlink
• Salon Stereo
• VCR/DVD
• Video
• Dinghy: AB for 9ppl with 50hp outboard
• Fishing Gear: 2 Casting rods
• Fishing Permit #: BVI Permit in Process
• Floating Mats
• Kayaks (2 Man)
• Snorkel Gear
• Stand-up Paddle Boards
• Tube
• Water Skis Kids

Captain: Roy Rucker Crew: Natalie Rucker, Pete Captain Roy Pat Rucker, Chef Natalie Rucker, and First Mate Pete bring a fun, welcoming, and deeply personal spirit to every charter aboard BAREFOOT COWBOY. Roy’s years of Virgin Islands sailing and technical experience pair with Natalie’s warm hospitality and guest-focused service, while Pete keeps morale high and ensures no snack goes unattended. Click each crew profile to learn more about their background, experience, and personal story. Captain: Roy Rucker 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/First Mate: Natalie Rucker 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- Friendly Pup: Pete 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.

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

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

Caribbean Terms