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Barefoot Cowboy

St Thomas USVI
58.00 Ft
10 pax
5 cabins
2 crew
5.0, 10 reviews
Cpt. Rucker Meet the crew
5.0, 10 reviews
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Barefoot Cowboy
Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)
58.00 Ft 10 pax 5 cabins 2 crew
Location:
Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)
Charter date:
Number of guests:
{{guestsCount}} pax
Weekly Charter Rate: $ 33,000
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APA: $ {{ yachtExtendedPricing.apa.amount.toLocaleString('en-US') }}
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All amounts are indicative. Final cost depends on yacht availability, signed contract, actual expenses and applicable tax law. VAT/Tax is based on embarkation port and itinerary. APA is an advance deposit, reconciled against actual costs at the end of the charter.
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Barefoot Cowboy

St Thomas USVI
58.00 Ft
10 pax
5 cabins
2 crew
5.0, 10 reviews
Cpt. Rucker Meet the crew
5.0, 10 reviews

What this yacht offers

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.

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ACCOMMODATION

1x Twin Cabins
Air conditioning
Grill on board
10
5x Shower
5x Toilets

Deck plan

Deck plan

ENTERTAINMENT

Audio System
Board games
WiFi

WATER ACTIVITIES

SUP board
Snorkling
Fishing gear

Other toys

9 Person Dinghy With 50HP
1 Subwing
1 2-Person Kayak
2 Stand Up Paddle Boards
1 Kids Water Ski
Towable Tube
2 Floating Mats
Snorkel Gear
Fishing Gear
Underwater Camera
2 Floating Chairs
Megachill
Foam Noodles
Dinghy Boarding Ladder
Beach Games
information

Delight served on deck

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

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Your starting place

Yacht Haven Grand
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10 reviews

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!!<br /> <br /> 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.<br /> <br /> 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!!!<br /> <br /> At no time did we feel like we were not in good hands.<br /> <br /> 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!!<br /> <br /> 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!!!<br /> <br /> 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!!<br /> 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!<br /> Take care,<br /> 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!<br /> <br /> 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! <br /> <br /> And Pete... what can I say? He's the sweetest little pirate out there and totally stole our hearts. <br /> <br /> 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. <br /> <br /> We're already counting down the days until we can return for more sailing, more sunshine, and more amazing memories!<br /> 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!<br /> <br /> 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!!<br /> <br /> 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!!<br /> 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.<br /> <br /> 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 reviews
See all

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!!<br /> <br /> 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.<br /> <br /> 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!!!<br /> <br /> At no time did we feel like we were not in good hands.<br /> <br /> 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!!<br /> <br /> 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!!!<br /> <br /> 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!!<br /> 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!<br /> Take care,<br /> 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!<br /> <br /> 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! <br /> <br /> And Pete... what can I say? He's the sweetest little pirate out there and totally stole our hearts. <br /> <br /> 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. <br /> <br /> We're already counting down the days until we can return for more sailing, more sunshine, and more amazing memories!<br /> 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!<br /> <br /> 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!!<br /> <br /> 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!!<br /> 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.<br /> <br /> Clare

Meet your crew

1 / 3

Meet your crew

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.

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Your starting place

Yacht Haven Grand
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{{tooltipText ?? 'Select the number of guests and your charter dates'}}

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+ expenses
$ {{ yachtPricing.toLocaleString('en-US') }}
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