Year Built

2015

Length

58 ft.

Designer

Leopard

Cabins

5

Guests

10

Rates From

$28,700


Experience the ultimate sea escape aboard the Leopard 58, Barefoot Cowboy. This luxurious yacht features a spacious, split-level floor plan designed for comfort and style.

On the main deck, two cabins open directly to a forward cockpit, while three additional cabins below offer private en-suite baths. All cabins are fully air-conditioned, ensuring a restful retreat. Inside, the well-appointed galley invites you to enjoy meals at the indoor dining area, complete with wrap-around seating for up to 10 guests.

Entertainment options abound with a 46” flat-screen TV/DVD player, onboard WiFi, Apple TV, and a CD stereo with MP3 connection.

Head up to the expansive flybridge, where you’ll find the helm station with a 360-degree view. Relax in stylish lounge seating, enjoy the electric grill, wet bar, and refrigerator, and gather with friends for cocktails as music plays through the sound system. It’s the perfect spot for dancing under the stars.

For al fresco dining, the aft deck boasts a stunning teak table that seats 10, providing an unforgettable view of the islands.

With accommodations for up to 10 guests, Barefoot Cowboy is your perfect escape for large groups seeking adventure, relaxation, and unforgettable memories at sea.

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.

DIVING: Offered via rendezvous only

TURN AROUND TIME: We prefer 48 hours in between charter drop off and pick ups, but feel free to inquire for 24. We will do our best to accommodate.

CRUISING GROUNDS: British Virgin Islands & U.S. Virgin Islands.

 
 

Booking Options & Availability

 

FULL-BOARD

Includes 7 breakfasts, 7 lunches and 7 dinners, happy hour canapes, standard ships bar and snacks. Meals ashore are additional.

2@$29,000 | 3@$29,500 | 4@$30,000 | 5@$30,500 | 6@$31,000 | 7@$31,500 | 8@$32,000 | 9@$32,500 | 10@$33,000

LOCAL FARE

Includes 7 breakfasts, 5 lunches and 6 dinners, happy hour canapes, standard ships bar and snacks. Meals ashore are additional.

2@$28,850 | 3@$29,275 | 4@$29,700 | 5@$30,125 | 6@$30,550 | 7@$30,975 | 8@$31,400 | 9@$31,825 | 10@$32,250

HALF-BOARD

Includes 7 breakfasts, 4 lunches and 3 dinners, happy hour canapes, standard ships bar and snacks. Meals ashore are additional.

2@$28,700 | 3@$29,050 | 4@$29,400 | 5@$29,750 | 6@$30,100 | 7@$30,450 | 8@$30,800 | 9@$31,150 | 10@$31,500

 

CHRISTMAS

7 night minimum
Full-board option only
Guests: 1-10 @ $40,000
Must end on or before 12/27
Please contact us for more information.

NEW YEARS

7 night minimum
Full-board option only
Guests: 1-10 @ $43,000
May not start prior to 12/28
Please contact us for more information.

SLEEP ABOARD

Sleep aboard the night before charter dates. Available for FREE! Includes boarding after 4pm, snacks, welcome cocktails & continental breakfast. Dinner ashore is additional. Select option upon booking. EXCLUDES: Christmas and New Year's weeks.

 

*To book a charter we have a 5-night minimum, but feel free to inquire for less.

 

Let’s Get Underway!

Does this yacht meet all of your requirements? Great! Let’s make your dream vacation a reality!

Our charter concierge is standing by ready to assist and answer any questions you may have so feel free to start a Live Chat (in the bottom right corner), submit an Inquiry Form or Call Us today!

Meet Your Crew

Capt. 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 has many favorite destination.  She loves jumping off Willy T at Norman Island with the guests.  She also loves being the tour guide through The Baths on Virgin Gorda.  Her number one goal is that the guest have the best experience and vacation while on Barefoot Cowboy.

 

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.

Crew Interview

Get to know this crew better with a hosted interview!

Please note, the third crewmate in this video, Madelline, is no longer onboard.

 

Dining With Chef Natalie

  • 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

  • SPECIALITY 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


Previous Guest Testimonials

  • 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

  • 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 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

    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!

  • November 2022

    Thank you so much for a fun trip! Captain Doyle and Chef Maya were amazing. The food was to DIE for! The activities, games, toys, and atmosphere were spectacular and something I’ll never forget. I will forever be grateful that this was our crew. You are both wonderful people and I will cherish our time together. I hope we get to meet again. Cheers to you.

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