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BAREFOOT COWBOY

$32,000 - $36,000 / WEEK
BAREFOOT COWBOY - 2
BAREFOOT COWBOY is a Leopard 58 built for big-group Caribbean fun and split-level space. Two main-deck Queen cabins open to the forward cockpit—ideal for easy access—while three cabins sit below for added privacy. Sleeping up to 10, she offers 5 air-conditioned cabins: 4 Queens plus 1 Twin (converts to a King), each with a private ensuite head and shower. Standout feature: the enormous flybridge with 360° views, helm lounge seating, wet bar, fridge, and electric grill—plus sound wiring for cocktails and a little dancing. Gather aft around the teak table for 10 for unforgettable al fresco meals. WiFi + Apple TV keep you connected—if you want to be. Bring your people—BAREFOOT COWBOY brings the vibe.
https://youtube.com/watch?v=zePVpVU0__8%3Fsi%3DlGetrjizVxT1H8v8
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Barefoot Cowboy Yacht Charter

Set sail on Barefoot Cowboy, a magnificent Leopard 58 catamaran that offers the perfect balance of luxury, adventure, and relaxation. Designed for comfort and style, this yacht boasts a spacious split-level floor plan, ensuring ample room for guests to unwind while taking in breathtaking ocean views. Whether you’re indulging in gourmet meals, soaking up the sun on the flybridge, or enjoying a sunset cocktail with friends, Barefoot Cowboy promises an unforgettable charter experience.

Unmatched Comfort & Accommodations

Accommodating up to 10 guests, Barefoot Cowboy features four queen cabins and a versatile twin cabin that can be converted into a king upon request. Each cabin is fully air-conditioned and equipped with a private en-suite bath, ensuring ultimate comfort and privacy. Thoughtfully designed interiors include a well-appointed galley, wrap-around seating for communal dining, and stylish furnishings that create a welcoming atmosphere for guests.

Elevated Onboard Experience

The yacht’s expansive flybridge is the perfect spot to enjoy 360-degree panoramic views while cruising through stunning island destinations. This space is designed for entertainment, featuring lounge seating, an electric grill, a wet bar, and a refrigerator to keep refreshments at hand. The flybridge is also wired for sound, making it the ideal place for music, dancing, and socializing under the stars. The aft deck provides another prime location for al fresco dining, complete with a beautifully crafted teak table for 10, offering an unbeatable backdrop of turquoise waters and island landscapes.

Advanced Technology & Upgrades

Barefoot Cowboy is outfitted with top-of-the-line electronics, including a RayMarine chart plotter, depth and wind monitoring systems, autopilot, and VHF radio. The main salon is equipped with a 46” Samsung LED TV, Bose surround sound, Apple TV, WiFi, and a Fusion entertainment system with Bluetooth connectivity, ensuring seamless entertainment throughout the journey.

Recent refits in 2023 and 2024 have enhanced the yacht’s amenities, including a newly installed water maker, solar panels, a powerful generator, and an upgraded air conditioning system. Additional upgrades include a new flybridge fridge, ice maker, and enhanced enclosures, ensuring a luxurious and seamless onboard experience.

Secure Your Exclusive Getaway

Why wait to embark on the adventure of a lifetime? Barefoot Cowboy offers a one-of-a-kind luxury yacht charter experience designed to create lasting memories. Book your dream escape today and cruise the open seas in unparalleled style and comfort!

4 Queens and 1 Twin. The twin cabin converts to a King upon request.

Electronics: RayMarine chart plotter, depth, wind and auto-pilot VHF Solon electronics include. 46" Samsung LED TV, Bose Surround sound system, Fusion entertainment system with blue tooth and wifi.

2023/2024 Refit:
2023-
Electric grill on the flybridge replaced.
All window blinds in state rooms replaced.
Flybridge enclosure replaced.
VHF radio replaced.
Ice Maker installed.
Fridge on the flybridge replaced.
6- 210 ah Lifeline AGM house batteries replaced..
Northern Lights 20kw generator replaced.
2024-
Water Maker replaced with Sea Recovery Aqua Matic.
Installed 6- 310w Solar Panels,Charge Controllers, GX Touch 70, Cerbo Gx and 500A/50mV Smartshunt.
New Generator
New AC unit/chilled water system

Free Sleepaboard! Details
BUILT/REFIT
YEAR
2015
YACHT
LENGTH
58 Ft
NUMBER OF
CABINS
5
NUMBER OF
GUESTS
10
TOTAL
CREW
2
CHARGES
FROM
$32,000
Accommodations
Cabins: 5
Queen: 4
Single Cabins: 1
Showers: 5
Electric Heads: 5
Engine Details
2, 110hp Yanmar engins, 1 22kw Norhtern Lights Generator
Fuel Consumption: -
Cruising Speed: 10
Max Speed: 20US Gall/Hr
Details
Type: Cat
Beam: 27 Feet
Draft: 5.7 Feet
Pax: 10
YearBuilt: 2015
Builder: Leopard
Engines: 2, 110hp Yanmar engins, 1 22kw Norhtern Lights Generator
JetSkis: No
Flag: US
SatTv: No
RegNum: VI7840TC
Jacuzzi: No
A/C: Full
Locations
Winter Area: Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)
Summer Area: Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)
Pick Up Locations
Pref. Pick-up: -
Other Pick-up: -


Amenities
Salon Tv/VCR: Yes
Salon Stereo: Yes
Sat Tv: Parents must bring life jackets for kids.
Camcorder: No
Books: Yes
Board Games: Yes
Deck Shower: Yes
Water Maker: Yes
Special Diets: Yes
Kosher: No
BBQ: Yes
Minimum Age: Any Age
Inverter: -
Voltages: 220/120v
Water Maker: Yes
Ice Maker: Yes
Sailing Instructions: No
Internet Access: Onboard WIFI
Hairdryers: Yes
Guests Smokes: Sugar Scoops only
Crew Smokes: No
Pets Aboard: Yes
Hammock: Yes
Water Sports
Dinghy size: AB
Dinghy hp: 50
Water Skis Adult: No
Water Skis Kids: Yes
Jet Skis: No
Kneeboard: No
Windsurfer: No
Snorkel Gear: Yes
Tube: Yes
Scurfer: No
Wake Board: No
Kayaks 1 Pax: No
Kayaks (2 Pax): 1
Floating Mats: 2
Swim Platform: -
Boarding Ladder (Loc/Type): -
Sailing Dinghy: No
Beach Games: -
Fishing Gear: Yes
Gear Type: 2 Casting
Rods: 2
Captain
Roy Pat Rucker
Nation: USA
Born: 1965
License: 100T
Chef / First Mate
Natalie Rucker
Nation: USA
Captain 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’s favorite destination is Dinghy’s on Water Island for Sunday Fundays and live music. She also loves Hull Bay for is quiet local vibe. For drinks, she’s a sucker for Diet Coke & Cruzan Rum and Margaritas!


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.

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

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!

10% will be discounted from the standard charter rate for charters started and completed between 11/18/23 and 12/17/23 – including Thanksgiving charters. The charter must be booked after 10/03/23, have a minimum of 5 nights and cannot be in conjunction with any other specials for the discount to apply.

Christmas charters are offered in the Virgin Islands at the STANDARD seasonal rate. Availability restrictions apply. The charter must be booked and completed before 1/07/2024. This special cannot be combined with other offers.

Rates are Inclusive
Season 2 PAX 3 PAX 4 PAX 5 PAX 6 PAX 7 PAX 8 PAX 9 PAX 10 PAX 11 PAX 12 PAX
Winter 2025 to 2026 $32,000 $32,500 $33,000 $33,500 $34,000 $34,500 $35,000 $35,500 $36,000
Summer 2026 $32,000 $32,500 $33,000 $33,500 $34,000 $34,500 $35,000 $35,500 $36,000
Winter 2026 to 2027 $32,000 $32,500 $33,000 $33,500 $34,000 $34,500 $35,000 $35,500 $36,000
Summer 2027 $32,000 $32,500 $33,000 $33,500 $34,000 $34,500 $35,000 $35,500 $36,000

Unless otherwise specified-Caribbean Standard All-Inclusive Charters include the following:

  • Standard check-in/check-out of 12pm
  • Light daily housekeeping
  • Breakfast, lunch, canapés/afternoon tea, dinner and snacks
  • Standard ship’s bar: vodka, gin, rum, whiskey, tequila, triple sec, mixers, local beers, table wine and water/coffee/tea and soft drinks
  • Stereo with MP3/iPhone connection with indoor/outdoor speakers; 3G/4G Wi-Fi access point
  • Snorkeling equipment, fishing gear, kayaks, dingy tender with outboard motors
  • Water toys such as floating islands, and air mattresses
  • Separate bathroom and living quarters for crew
  • Reputable and licensed crew who have local knowledge of waters and are able to adjust menus based on guest’s preferences and dietary restrictions
  • Operating expenses including: use of air conditioning, fuel, water, sailing permits/taxes, local taxes and crew wages

What Is Not Included in Standard All-Inclusive Charters:

  • Gratuity for crew. Gratuity is at guest discretion and is typically between 15-20%
  • Meals and beverages at restaurants and bars
  • Rendezvous diving, ASA sailing certification courses and any other offshore excursions
  • Premium wines and spirits
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 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

X

Available

X

Booked

X

Hold

X

Unavailable

  • : Cat
  • : 27 Feet
  • : 5.7 Feet
  • : 10
  • : 2015
  • : Leopard
  • : 10
  • : 20
  • : 2, 110hp Yanmar engins, 1 22kw Norhtern Lights Generator
  • : Yes
  • : No
  • : Yacht offers Rendezvous Diving only
  • : Roy Pat Rucker
  • : US
  • : No
  • : VI7840TC
Accommodations
Cabins: 5
Queen: 4
Single Cabins: 1
Showers: 5
Wash Basins: 5
Heads: -
Electric Heads: 5
Engine Details
2, 110hp Yanmar engins, 1 22kw Norhtern Lights Generator
Fuel Consumption: -
Cruising Speed: 10
Max Speed: 20US Gall/Hr
Details
Refit: -
Helipad: No
Jacuzzi: No
A/C: Full
Locations
Winter Area: Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)
Summer Area: Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)
Pick Up Locations
Pref. Pick-up: -
Other Pick-up: -


Amenities
Salon Tv/VCR: Yes
Salon Stereo: Yes
Sat Tv: Parents must bring life jackets for kids.
# of Videos: -
# DVDs/Movies: Yes
# CD's: Yes
Camcorder: No
Books: Yes
Board Games: Yes
Sun Awning: -
Deck Shower: Yes
Bimini: -
Water Maker: Yes
Special Diets: Yes
Kosher: No
BBQ: Yes
# Dine In: 10
Minimum Age: Any Age
Generator: 1 22kw Norhtern Lights Generat
Inverter: -
Voltages: 220/120v
Water Maker: Yes
Water Cap: -
Ice Maker: Yes
Sailing Instructions: No
Internet Access: Onboard WIFI
Gay Charters: Inq
Nude: Inq
Hairdryers: Yes
# Port Hatches: -
Guests Smokes: Sugar Scoops only
Crew Smokes: No
Pets Aboard: Yes
Pet Type: Very calm and friendly small dog, Pete
Guest Pets: No
Children Ok: Yes
Hammock: Yes
Windscoops: -
Water Sports
Dinghy size: AB
Dinghy hp: 50
Dinghy # pax: 9
Water Skis Adult: No
Water Skis Kids: Yes
Jet Skis: No
Wave Runners: No
Kneeboard: No
Windsurfer: No
Snorkel Gear: Yes
Tube: Yes
Scurfer: No
Wake Board: No
Kayaks 1 Pax: No
Kayaks (2 Pax): 1
Floating Mats: 2
Swim Platform: -
Boarding Ladder (Loc/Type): -
Sailing Dinghy: No
Beach Games: -
Fishing Gear: Yes
Gear Type: 2 Casting
Rods: 2
Captain
Roy Pat Rucker
Nation: USA
Born: 1965
License: 100T
Chef / First Mate
Natalie Rucker
Nation: USA
Captain 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’s favorite destination is Dinghy’s on Water Island for Sunday Fundays and live music. She also loves Hull Bay for is quiet local vibe. For drinks, she’s a sucker for Diet Coke & Cruzan Rum and Margaritas!


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.

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

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!
Rates are Inclusive
Season 2 PAX 3 PAX 4 PAX 5 PAX 6 PAX 7 PAX 8 PAX 9 PAX 10 PAX
Winter 2025 to 2026 $32,000 $32,500 $33,000 $33,500 $34,000 $34,500 $35,000 $35,500 $36,000
Summer 2026 $32,000 $32,500 $33,000 $33,500 $34,000 $34,500 $35,000 $35,500 $36,000
Winter 2026 to 2027 $32,000 $32,500 $33,000 $33,500 $34,000 $34,500 $35,000 $35,500 $36,000
Summer 2027 $32,000 $32,500 $33,000 $33,500 $34,000 $34,500 $35,000 $35,500 $36,000

Unless otherwise specified-Caribbean Standard All-Inclusive Charters include the following:

  • Standard check-in/check-out of 12pm
  • Light daily housekeeping
  • Breakfast, lunch, canapés/afternoon tea, dinner and snacks
  • Standard ship’s bar: vodka, gin, rum, whiskey, tequila, triple sec, mixers, local beers, table wine and water/coffee/tea and soft drinks
  • Stereo with MP3/iPhone connection with indoor/outdoor speakers; 3G/4G Wi-Fi access point
  • Snorkeling equipment, fishing gear, kayaks, dingy tender with outboard motors
  • Water toys such as floating islands, and air mattresses
  • Separate bathroom and living quarters for crew
  • Reputable and licensed crew who have local knowledge of waters and are able to adjust menus based on guest’s preferences and dietary restrictions
  • Operating expenses including: use of air conditioning, fuel, water, sailing permits/taxes, local taxes and crew wages

What Is Not Included in Standard All-Inclusive Charters:

  • Gratuity for crew. Gratuity is at guest discretion and is typically between 15-20%
  • Meals and beverages at restaurants and bars
  • Rendezvous diving, ASA sailing certification courses and any other offshore excursions
  • Premium wines and spirits
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 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
CONTACT US