BAREFOOT COWBOY






































- Amenities Details
- 7-Night Rates
- Availability
- Specifications
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.
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2 Stand Up Paddle Boards
1 Bote 2 Person Inflatable Kayak
2 Bote Floating Chairs
Megachill
Noodles
Underwater Camera
Snorkeling Gear
Tubes
1 Subwing
2 Fishing Rods
Onshore Games.
Dinghy Boarding Ladder
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Offered via rendezvous only
- 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: $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: $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: $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
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 2025 / 2026 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
Summer Base Port:USVI / BVI
Summer Operating Area:Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)
Winter Base Port:USVI / BVI
Winter Operating Area: Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)
Location Details:
Check Charter Availability by Month
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Specifications
Locations
YHG | AYH STT
Amenities
Water Sports
Other Toys
2 Stand Up Paddle Boards
1 Bote 2 Person Inflatable Kayak
2 Bote Floating Chairs
Megachill
Noodles
Underwater Camera
Snorkeling Gear
Tubes
1 Subwing
2 Fishing Rods
Onshore Games.
Dinghy Boarding Ladder
- Year Built 2015
- Length 58 ft.
- Designer Leopard
- Cabins 5
- Maximum Guests 10
- Starting From $26,367
*2 Guests, 5 Nights with Half-Board Meal Package
Got a Question? We’ve Got Answers.
Meet our Crew
Natalie Rucker
Desserts
DAY BREAK
- DAY BREAKAll 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
Crew Interview
Get to know this crew better with a hosted interview!
Guest Testimonials
April 2025
Fantastic. I noted to Capt. Roy Pat and Natalie about halfway through the trip that I thought we were lucky and so grateful to have gotten THEM as our crew. As we progressed through the trip and saw the other boats and people with their crew out at restaurants, I knew we had won the lottery! Capt. Roy Pat, Natalie and Jenna were wonderful, totally our speed, and we really enjoyed getting to know them and hear their stories!!
Everything from ID’ing fish to answering questions about the various areas we visited to recipe questions…. There was nothing they didn’t know! We truly enjoyed getting to know them and we trusted everything they had to say, from restaurant options down to changing course because of the rough seas and winds.
We wanted for nothing all week. Emily and I felt a tad strange not helping with cleaning up… and it felt a little weird to be catered to when we are all used to doing everything on our own. That isn’t necessarily a negative!! Ha! Just took some getting used to!!!
At no time did we feel like we were not in good hands.
WE LOVED NATALIE’S FOOD. I think we would have done ALL meals on the boat had that been an option. I loved her food so much, that I looked through her cookbook and took pics of recipes!!! We told her we ate a LOT, and she nailed it!!
We did not want to leave and we are already trying to figure out when we could come back! Doing this trip with family was amazing. The kids get along so well. No one ever got bored. No snippy bickering. We truly got to relax and decompress from work, school, and sports. It was the perfect vacation!!!
Our most memorable highlight was the “Highs and Lows” discussion at the end of the day with everyone. What a special way to cement the memories made that day and hear what everyone else thought about their day!! We are grateful to Capt. Roy Pat and Natalie for introducing us to that little end-of-day discussion idea!!! Of course, the food, snorkeling, diving, laughs, island hopping, sunburns, sleeping in the beanbags, reading in the shade, fun conversations, etc…. Soooo many things made the highlight reel in our minds!!
Natalie
April 2025
We had a fabulous vacation sailing through the BVI's on Barefoot Cowboy! Many thanks to you for linking us up with Captain Roy Pat & Natalie. We appreciate all the information and communication you provided us with leading up to our trip. We would absolutely give the 9 items you listed a 10 out of 10. Roy Pat, Natalie & Jenna were so kind, helpful, knowledgeable and professional throughout the entire trip. They knew we were an active group and did a great job of finding fun spots for us to snorkel & explore. The meals they prepared were delicious and always crowd pleasers! Highlights for us were definitely seeing all the awesome sea life on our snorkeling adventures, exploring The Baths on Virgin Gorda, and just spending quality time together as a family. Thanks again for helping us organize an unforgettable vacation!
Take care,
Emily & Justin
April 2025
We just returned from a glorious 7 days aboard the Barefoot Cowboy, and we're already dreaming about when we can return. To say we were spoiled would be an understatement!
Captain Roy Pat was phenomenal-navigating us to all the best spots throughout the Virgin Islands with such expertise - every day felt like a new adventure. Chef Natalie absolutely blew us away with every single meal. You could truly taste the heart and soul she put into her cooking. My personal favorites? The perfectly cooked filet mignon for dinner and the fresh, flavorful chicken avocado salad for lunch-both were out of this world!
And Pete... what can I say? He's the sweetest little pirate out there and totally stole our hearts.
This was our first trip to the Virgin Islands, and we couldn't have asked for a better introduction. We loved every stop-Willy T's, Cooper Island, everything about Jost Van Dyke, and the beauty of St. John. Every day brought something new and unforgettable.
We're already counting down the days until we can return for more sailing, more sunshine, and more amazing memories!
Lori
March 2025
We loved the front trampolines and all the extras on the yacht! The paddle boards and the mega chill were a huge hit. There was nothing we missed. They had everything!! One tiny down side was the bathroom sizes but you can live with it for a week or two in paradise. We loved the crew!! The yacht pup was the cutest extra!
This was an absolute trip of a lifetime for us!! We loved every single second of our time on the boat and on the islands!!
Mandie
June 2024
We sailed with Roy Pat, Natalie and pirate Pete June 2024. It was without a doubt the most amazing vacation. Words can't describe the hospitality that was received and the friendships that were made. I highly recommend sailing with Barefoot Cowboy, simply the best!!
Kathy
January 2025
This was the best family vacation we ever had! Roy and Natalie were incredible hosts! From accommodations to the food to the fun! Highly recommend.
Clare
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!