$33,000 - $37,000 / WEEK
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BUILT/REFIT
YEAR
2023
Yacht
Length
58.00 Ft
NUMBER OF
CABINS
5
NUMBER OF
GUESTS
10
TOTAL
CREW
2
CHARGES
FROM
$33,000
Layout
BAREFOOT COWBOY
58 Feet
Cat
#Pax
10
Beam
27
Draft
5.7
Built
2015
Make
Leopard
Refit
2023
#Cabins
5
Cabin Configuration
4Queen(s), 1Twin(s)
Showers
5
Tubs
0
Wash Basins
5
Heads
0
Elec. Heads
5
Helipad
No
Jacuzzi
No
Gym
No
A/C
Full
Pref. Pick-up
Yacht Haven Grand
Other Pick-up
Turn-around
C. Permit
1
License
1
Engines/Generators
2, 110hp Yanmar engins, 1 22kw Norhtern Lights Generator
Range
Fuel Consumption
Cruising Speed
10
Max Speed
20
Accommodations
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.
Locations
Summer Ports
St Thomas USVI
Summer Operations
Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)
Location Details
N/A
Winter Ports
St Thomas USVI
Winter Operations
Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)
MCA Compliance
N/A
Amenities
Salon Tv
No
Salon Stereo
No
SAT Tv
-
iPod/Device Hookups
-
Sun Awning
No
Hammock
No
Windscoops
No
Deck Shower
No
Bimini
No
Nude Charters
Inq
Hairdryers
Yes
#Port Hatches
No
Crew Smokes
No
Guest Smokes
Sugar Scoops only
Pets Aboard
No
Pet Type
-
Guest Pets
No
Elevators
No
Wheel Chair Access
No
Water Maker
yes
Water Capacity
-
Ice Maker
-
Stabilizers
No
Sailing Instructions
-
Internet Access
-
Green Initiatives
Make purified drinking water?
Yes
Re-usable water bottles
Yes
Other Green Initiatives
-
Children Details
Children Allowed
Yes
Minimum Child Age
Swim Safe
Diet Details
Special Diets
Yes
Kosher
No
BBQ
No
#Dine-In
No
Power Details
Generator
-
Fuel
-
Inverter
No
Voltages
-
Dinghy Details
Dinghy
No
Dinghy Hp
-
Dinghy Pax
-
Water Sports
Water Skis Adult
No
Water Skis Kids
No
Jet Skis
No
Wave Runners
No
KneeBoard
No
Windsurfer
No
Snorkel Gear
No
Tube
No
Scurfer
No
WakeBoard
No
Kayaks (1 Pax)
No
Kayaks (2 Pax)
No
Floating Mats
No
Swim Platform
No
Boarding Ladder (Loc/Type)
No
Sailing Dinghy
-
Beach Games
No
SU Paddle Board
No
Fishing Gear
No
Gear Type
-
Rods
-
Deep Sea Fish
No
Under Water Camera
No
Under Water Video
No
Fish Permit
BVI Permit in Process
Sea Bob
No
Sea Scooter
No
Kite Boarding
No
Kite Boarding Details
-
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
Other Amenities
Eisenglass Weather Protection
Parents must bring life jackets for kids
Communications
-
Total Crew Members
2
Crew Name
Natalie Rucker
Crew Title
Chef/First Mate
Crew Nationality
American
Captain Name
Roy Rucker
Captain Nationality
American
Captain Language
English
Captain Born
-
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.
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
Start Date : Jul 12, 2026
End Date : Oct 31, 2026
Details : Unavailable: Unavailable to Unavailable
Start Date : Nov 08, 2026
End Date : Nov 14, 2026
Details : Booked: St Thomas, USVI to St Thomas, USVI
Start Date : Nov 22, 2026
End Date : Nov 28, 2026
Details : Booked: Yacht Haven Grand to Yacht Haven Grand
Start Date : Dec 27, 2026
End Date : Jan 03, 2027
Details : Booked: Yacht Haven Grand to Yacht Haven Grand
Start Date : Jan 06, 2027
End Date : Jan 11, 2027
Details : Booked: St Thomas USVI to St Thomas USVI
Start Date : Jan 18, 2027
End Date : Jan 26, 2027
Details : Booked: St Thomas, USVI to St Thomas, USVI
Start Date : Jan 30, 2027
End Date : Feb 06, 2027
Details : Booked: St Thomas, USVI to St Thomas, USVI
Start Date : Mar 06, 2027
End Date : Mar 13, 2027
Details : Booked: St Thomas, USVI to St Thomas, USVI
Start Date : Apr 11, 2027
End Date : Apr 18, 2027
Details : Booked: St Thomas, USVI to St Thomas, USVI
Start Date : Apr 24, 2027
End Date : May 01, 2027
Details : Unavailable: St Thomas USVI to St Thomas USVI
Start Date : May 22, 2027
End Date : May 29, 2027
Details : Booked: Unavailable to Unavailable
Start Date : Mar 04, 2028
End Date : Mar 11, 2028
Details : Booked: St Thomas, USVI to St Thomas, USVI
High Rate: 37000 USD per week
MCA Compliant:
Low Rate: 33000 USD per week
Seasonal/Individual Rates
Season:
Additional Rates & Notes
Currency:
USD
Terms:
(Caribbean Terms) Inclusive
Winter 2026 to 2027
USD
(Caribbean Terms) Inclusive
$33,000
$33,500
$34,000
$34,500
$35,000
$35,500
$36,000
$36,500
$37,000
Summer 2027
USD
(Caribbean Terms) Inclusive
$33,000
$33,500
$34,000
$34,500
$35,000
$35,500
$36,000
$36,500
$37,000
Winter 2027 to 2028
USD
(Caribbean Terms) Inclusive
$33,000
$33,500
$34,000
$34,500
$35,000
$35,500
$36,000
$36,500
$37,000
Summer 2028
USD
(Caribbean Terms) Inclusive
$33,000
$33,500
$34,000
$34,500
$35,000
$35,500
$36,000
$36,500
$37,000
Captain Only Rates:
-
Additional 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
Summer Base Port:
St Thomas USVI
Summer Operating Area:
Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)
Winter Base Port:
St Thomas USVI
Winter Operating Area:
Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)
Location Details:
-
Guest Comments
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!
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
It’s was all we dreamed it would be…Food was delicious and beautifully served…The staff exceptional, will go every chance we get!!!
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!
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
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
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
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
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