BVISAIL
“You Make the Memories, We’ll Make the Arrangements”
BAREFOOT COWBOY

Caribbean Virgin Islands (US/BVI) · Caribbean Virgin Islands (BVI) · Caribbean Virgin Islands (US)

BAREFOOT COWBOY

Catamaran 58 feet 10 Guests 5 Cabins 2 Crew Built 2015

From

$33,000 / week

Request This Yacht

Length

58 feet

Guests

10

Cabins

5

Crew

2

Built / Refit

2015 / 2023

Type

Catamaran

Cruising Speed

10 knots

Max Speed

20 knots

Beam

27

Draft

5.7

Overview

Charter BAREFOOT COWBOY

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.

Pricing & Seasons

Charter Rates by Season

Additional Rates & Notes

Low Season

Jun 26, 2026 - Oct 26, 2030

From Inquire / week

Inclusive Charter · Caribbean Terms

Cruising Grounds: Caribbean Virgin Islands (US/BVI)

Winter 2026 to 2027

High Season

Nov 1, 2026 - Apr 30, 2027

From $33,000 / week

Inclusive Charter · Caribbean Terms

Cruising Grounds: Caribbean Virgin Islands (BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (US/BVI)

Summer 2027

Low Season

May 1, 2027 - Oct 31, 2027

From $33,000 / week

Inclusive Charter · Caribbean Terms

Cruising Grounds: Caribbean Virgin Islands (BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (US/BVI)

Winter 2027 to 2028

High Season

Nov 1, 2027 - Apr 30, 2028

From $33,000 / week

Inclusive Charter · Caribbean Terms

Cruising Grounds: Caribbean Virgin Islands (BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (US/BVI)

Summer 2028

Low Season

May 1, 2028 - Oct 31, 2028

From $33,000 / week

Inclusive Charter · Caribbean Terms

Cruising Grounds: Caribbean Virgin Islands (BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (US/BVI)

Rate 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

Accommodation

5 Cabins, 10 Guests

4 Queen Cabins
1 Twin Cabins
5 Showers

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.

Specifications

Technical Details

Builder Leopard
Year Built 2015
Last Refit 2023
Length Overall 58 feet
Beam 27
Draft 5.7
Cruising Speed 10 knots
Maximum Speed 20 knots
Fuel Consumption 1
Watermaker yes
Air Conditioning Full
Flag US

2, 110hp Yanmar engins, 1 22kw Norhtern Lights Generator

Crew

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.

Roy Rucker

Roy Rucker

Captain

American · English

Captain Roy Rucker
Captain Roy Pat Rucker has been helping guests enjoy unforgettable charter vacations since 2013. A Texas-born-and-raised cowboy, he grew up working on ranches and participating in rodeos before building a life centered around the sea.

Roy has spent more than four years sailing throughout the Virgin Islands and is also a certified advanced diver. Before fully embracing charter life, he spent 30 years with BP, working in a variety of technical and leadership roles including mechanic, lead technician, maintenance team leader, fireteam leader, and maintenance planner. His career took him aboard offshore platforms in the Gulf of Mexico and the Caspian Sea off the coast of Azerbaijan.

In 2017, Roy lost his charter yacht, THREE MOONS, during Hurricane Maria in Puerto Rico. The loss was devastating, but it also reminded him how deeply he loved life on the water and sharing it with others.

Determined to begin again, Roy and his wife, Natalie, purchased a catamaran together and returned to chartering. Today, he brings technical knowledge, calm leadership, and genuine enthusiasm to every trip, helping guests experience the beauty, adventure, and relaxed rhythm of the Virgin Islands.

 

 

Natalie Rucker

Natalie Rucker

Chef/First Mate

American · English

Chef Natalie Rucker
Chef Natalie Rucker spent 29 years working as a certified optician, where she developed a strong talent for customer service and creating personalized experiences. That same thoughtful, people-focused approach now shapes the way she cares for guests onboard.

Natalie loves helping guests eat well, enjoy great drinks, and make the most of every moment on charter. Her warm personality and natural hospitality create an easygoing atmosphere where guests feel comfortable, welcomed, and well looked after.

She enjoys tailoring the experience to each group, from meals and cocktails to favorite island stops and relaxed afternoons on the water. And, as an added bonus, she can even adjust your sunglasses if you happen to sit on them.

Some of Natalie’s favorite local spots include Dinghy’s on Water Island for Sunday Fundays and live music, and Hull Bay for its quiet, local feel. Her drink of choice is Diet Coke with Cruzan Rum, though she is always happy to enjoy a good margarita as well.

 

 

Pete

Pete

3rd Mate- Friendly Pup

Miniature Wirehaired Dachshund · Woof Woof

3rd Mate Pete
Pete is a handsome, well-mannered Miniature Wirehaired Dachshund and a much-loved member of the crew aboard BAREFOOT COWBOY. At five years old, he takes his duties seriously, especially when it comes to keeping everyone onboard smiling.

Laid-back and affectionate, Pete enjoys riding in the dinghy, taking long walks on the beach, swimming, chasing reflections, and fitting in plenty of naps between activities. When off duty, he can often be found close beside Captain Roy.

Pete has already made more than 200 friends during his first year of service and is especially popular with dockhands, who frequently stop by to say hello and bring him treats.

He also takes his role as Security Officer very seriously. Any food dropped on deck is inspected and removed immediately, helping keep BAREFOOT COWBOY clean, secure, and snack-free at all times.

Watersports & Toys

Play On & Off the Water

Dinghy Fishing Gear Fishing Permit # Floating Mats Kayaks (2 Man) Snorkel Gear Stand-up Paddle Boards Tube Water Skis Kids

Onboard 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
 

Cuisine

Menu & Dining

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

Dinner

Dinner

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

Dinner

Dinner

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

Dinner

Dinner

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

Lunch

Lunch

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

Sweets

Sweets

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

Dinner

Dinner

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

Amenities

Everything Onboard

BBQ
Board Games
Books
CDs
Deck Shower
Dining
DVDs
Generator
Smoking Allowed
Hair Dryer
Hammock
Ice Maker
iPod/MP3
Internet/WiFi
Salon Stereo
VCR/DVD
Video

Charter Preferences

Kosher: No Special Diets: Yes Gay Charters: Inq Nude Charters: Inq Crew Smoke: No

Availability

Check Open Dates

October 2026
Available On Hold Booked
1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31

Availability is updated in real time — contact us to confirm exact dates for your travel window.

Guest Reviews

10 Guest 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!!

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

Showing 6 of 10 reviews

Planning Help

Why Charter With Us

Based on her specifications and charter profile, BAREFOOT COWBOY is well suited for groups of up to 10 guests seeking a comfortable crewed charter in Caribbean Virgin Islands (US/BVI). The combination of 5 cabins, 58 feet of living space, and a proven charter layout makes her a practical choice for families and groups who value both comfort and privacy.

Before recommending any yacht, our charter brokers review availability, charter rates, seasonal demand, crew feedback, onboard amenities, and destination suitability. If BAREFOOT COWBOY isn't the perfect fit, we'll recommend comparable yachts to ensure you book the best option for your travel dates and preferences.

How do I check if this yacht is available?

Availability changes daily. Submit your preferred travel dates and our charter specialists will confirm availability and provide the latest pricing. If this yacht is unavailable, we'll recommend similar alternatives.

Is the displayed price final?

The weekly charter rate is a starting price. Final pricing depends on your travel dates, destination, season, applicable taxes, and additional expenses such as APA, fuel, dockage, and gratuities where applicable.

What is included in a yacht charter?

Most yacht charters include the yacht, professional crew (if crewed), onboard accommodations, standard water toys, and insurance. Additional expenses vary depending on the yacht and itinerary.

Can I customize my itinerary?

Yes. Every yacht charter itinerary is customized around your preferred destinations, travel dates, weather conditions, and interests.

How far in advance should I book?

Luxury yachts are often reserved several months in advance, especially during peak seasons. Early booking provides the best selection and pricing.

Do I need sailing experience?

No. Most luxury yacht charters include an experienced captain and professional crew who handle navigation and daily operations.

Can you recommend similar yachts?

Absolutely. If this yacht isn't the perfect match, our charter experts can recommend similar yachts based on your budget, group size, destination, and preferred amenities.

Which destinations can this yacht visit?

Cruising areas depend on the yacht's seasonal location. Our charter team will recommend the best itinerary based on your travel dates.

Can I book this yacht online?

Availability and pricing change frequently, so we recommend submitting an inquiry. A charter specialist will prepare a personalized proposal.

Why should I book through BVI Sail?

Our charter specialists compare hundreds of verified yachts, provide independent recommendations, and help you choose the best option for your vacation without additional booking fees.

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From $33,000 / week

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