VIRGIN ISLANDS CHARTER YACHTS:
1-800-596-0594
BAREFOOT COWBOY
BAREFOOT COWBOY
| Length: | 58 ft |
|---|---|
| Builder: | Leopard |
| Year Built: | 2015 |
| Refit: | 2023 |
| Max Guests: | 10 |
| Cabins: | 5 |
| # Crew: | 2 |
| Max Speed: | 20 |
| Cruising: | 10 |
| Beam: | 27 ft |
| Draft: | 5.7 ft |
| Base Port: | St Thomas USVI |
Accomodations:
| 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. | |
| Queens: | 4 |
|---|---|
| Twin Cabins: | 1 |
Charter Yacht BAREFOOT COWBOY : 2015 58 ft Leopard Catamaran
Scuba Diving
| Scuba: | Rendezvous Not Included |
|---|
Water Toys
| Other Toys: | |
|---|---|
| 9 Person Dinghy With 50HP | |
Entertainment
| Internet: | Starlink |
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| Other: | |
| Eisenglass Weather Protection Parents must bring life jackets for kids | |
Amenities | |
| AC: | Full |
| AC Night: | yes |
| AC Surcharge: | no |
| Hair Dryer: | Yes |
| Special Diets: | Yes |
| Kosher Diets: | No |
| Nude Charters: | Inq |
| Guest Smoke: | Sugar Scoops only |
| Crew Smokes: | No |
| Guest Pet: | No |
| Children?: | Yes |
| Min Age: | Swim Safe |
- Booked
- On Hold
- Available
- Unavailable
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Crew Profile
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.
Sample Menu
Freshly prepared cuisine featuring relaxed breakfasts, flavorful midday favorites, plated dinners, sweet finishes, and cocktails crafted for life aboard. Sample menu selections are listed below and may vary based on guest preferences, provisioning, and chef creativity.
DAY BREAK
All served with a fresh fruit platter, coffee & breakfast cocktails of choice
Fresh Blueberry Pancakes with a Side of Bacon and/or Sausage and Eggs Made to Order
Classic Eggs Benedict with a Side of Roasted Potatoes
Biscuit Charcuterie Board
Cheesy Spinach and Bacon Quiche with a Side of Crispy Hashbrowns
French Toast Topped with Fresh Strawberries and Whipped Cream, Side of Bacon and/or Sausage and Eggs Made to Order
Build Your Own Breakfast Tacos with Choices of Eggs, Potatoes, Cheese, Green Chilies, Bacon & Sausage
Homemade Banana Bread
MIDDAY
Garlic Steak Bites Served with Assorted Cheeses, Avocado & Toasted Baguette Slices
Local Mahi Mahi Tacos with Slaw, Pineapple Mango Salsa & Sriracha Mayo
Yellowfin Tuna Poke Bowls Served Over Sushi Rice Topped with Yum Yum Sauce & Avocado Slices
Cheeseburgers in Paradise with Your Choice of Toppings Served with Pasta Salad
Chicken, Steak, or Cheese Quesadillas Drizzled with a Spicy Sour Cream Sauce
HORS D’OEUVRES
Garlic & Herb Cream Cheese Crostinis Topped with Prosciutto, Arugula & Pepper Jelly
Prosciutto Wrapped Melon with Balsamic Glaze
Charcuterie Board
Dip Trio Consisting of Guacamole, Queso & Salsa Served with Tortilla Chips
Baked Brie with Raspberry Jalapeño Jam and Assorted Crackers
MAIN
Grilled Snapper, Creamy Mushroom Risotto & Bacon Wrapped Asparagus
Cheese Tortellini Topped with Homemade Spinach Alfredo Sauce & Blackened Chicken
Caribbean Lobster, Filet Mignon, Whipped Potatoes & Roasted Green Beans
Lasagna Puttanesca with Cheesy Garlic Bread and Garden Salad
Lime in Duh Coconut Mahi Mahi with Mango Salsa and Coconut Lime Rice
DESSERT
Southern Key Lime Pie
Crème Brûlée
Lemon Bars
Tiramisu
The Most Amazing Chocolate Cake
Carrot Cake with Cream Cheese Icing
Chocolate Mousse
Grandma’s Blackberry Apple Crumble
SHIP'S BAR
Tito’s | Grey Goose | Deep Eddy Lemon
Tanqueray | Bombay Sapphire
Milagro Blanco | Repasado
Bulleit Bourbon | Crown Royal
Cruzan Dark | Cruzan Light | Cruzan Coconut | Cruzan Passion Fruit | Cruzan Mango | Cruzan Tropical Fruit
Cointreau | Grand Marnier | Aperol
Coke | Diet Coke | Ginger Beer | Club Soda | Ting | Pink Ting | Orange Juice | Pineapple Juice
Passion Fruit Juice | Cranberry Juice | Bloody Mary Mix | Cream of Coconut
SPECIALTY COCKTAILS
Painkiller with Cruzan Dark Rum, Pineapple Juice, Orange Juice, Cream of Coconut
Rum Punch with Cruzan Light Rum, Orange Juice, Pineapple Juice & Grenadine
Margarita with Milagro, Cointreau & Freshly Squeezed Lime Juice (Additions: Watermelon, Coconut, Spicy)
Cosmopolitan with Tito’s, Cointreau & Cranberry Juice
Moscow Mule with Tito’s, Ginger Beer & Freshly Squeezed Lime Juice
Rates
| SEASON: |
|---|
| Additional Rates & Notes |
| Winter 2026 to 2027 |
| Summer 2027 |
| Winter 2027 to 2028 |
Preferred Pickup: Yacht Haven Grand
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
• 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
Rate Terms:
InclusiveAll rates are for the entire yacht and are subject to change without notice prior to actual reservation.
An additional premium maybe applied for Holiday Periods such as Christmas and New Year.