Cruising Area of Barefoot Cowboy
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.
Barefoot Cowboy Specification
2, 110hp Yanmar engins, 1 22kw Norhtern Lights Generator
Water Sports
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
Scuba Diving 
Entertainment
Eisenglass Weather Protection
Parents must bring life jackets for kids
Cuisine
Green Initiatives
Barefoot Cowboy Crew Profile
Captain
Chef/First Mate
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.
Barefoot Cowboy Calendar
AvailableBookedHold (can be challenged)Unavailable| Aug 2026 | 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 |
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| Sep 2026 | 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 | |
| Oct 2026 | 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 |
| Nov 2026 | 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 | |
| Dec 2026 | 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 |
| Jan 2027 | 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 |
| Feb 2027 | 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 | |||
| Mar 2027 | 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 |
| Apr 2027 | 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 | |
| May 2027 | 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 |
| Jun 2027 | 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 | |
| Jul 2027 | 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 |
| Aug 2027 | 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 |
| Sep 2027 | 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 | |
| Oct 2027 | 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 |
| Nov 2027 | 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 | |
| Dec 2027 | 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 |
| Jan 2028 | 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 |
| Feb 2028 | 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 | ||
| Mar 2028 | 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 |
| Apr 2028 | 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 | |
| May 2028 | 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 |
| Jun 2028 | 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 | |
| Jul 2028 | 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 |
Barefoot Cowboy Reservations & Port Locations
| Start Date | End Date | Details (Holds can be challenged) |
|---|---|---|
| Jul 12, 2026 | Oct 31, 2026 | Unavailable: Unavailable to Unavailable |
| Nov 08, 2026 | Nov 14, 2026 | Booked: St Thomas, USVI to St Thomas, USVI |
| Nov 22, 2026 | Nov 28, 2026 | Booked: Yacht Haven Grand to Yacht Haven Grand |
| Dec 27, 2026 | Jan 03, 2027 | Booked: Yacht Haven Grand to Yacht Haven Grand |
| Jan 06, 2027 | Jan 11, 2027 | Hold: St Thomas USVI to St Thomas USVI |
| Jan 18, 2027 | Jan 26, 2027 | Booked: St Thomas, USVI to St Thomas, USVI |
| Jan 30, 2027 | Feb 06, 2027 | Booked: St Thomas, USVI to St Thomas, USVI |
| Mar 06, 2027 | Mar 13, 2027 | Booked: St Thomas, USVI to St Thomas, USVI |
| Apr 11, 2027 | Apr 18, 2027 | Booked: St Thomas, USVI to St Thomas, USVI |
| Apr 24, 2027 | May 01, 2027 | Unavailable: St Thomas USVI to St Thomas USVI |
| May 12, 2027 | May 19, 2027 | Booked: Unavailable to Unavailable |
| Mar 04, 2028 | Mar 11, 2028 | Booked: St Thomas, USVI to St Thomas, USVI |
Barefoot Cowboy Rates / week
The prices shown are for the entire yacht for a week-long (7 nights) charter.Low price: $32,000
High price: $37,000
| Season | 2 Pax | 3 Pax | 4 Pax | 5 Pax | 6 Pax | 7 Pax | 8 Pax | 9 Pax | 10 Pax |
|---|---|---|---|---|---|---|---|---|---|
| 2026 Summer | $32,000 | $32,500 | $33,000 | $33,500 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 |
| 2026/27 Winter | $33,000 | $33,500 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 | $36,500 | $37,000 |
| 2027 Summer | $33,000 | $33,500 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 | $36,500 | $37,000 |
Yacht terms: All Inclusive
An all-inclusive charter covers all provisioning and running expenses. This includes a captain and crew that is fully trained and committed to your safety and enjoyment of your trip. A chef will provide the kind of exceptional, personalized meal preparation that you would expect of a five-star restaurant. The listed rate may not include all local taxes, cruising permits, premium beverages and scuba activities. Inquire for more information.
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
MINIMUM CHARTER NIGHTS: 5-night minimum / Shorter charters considered on request
SHORT-TERM CHARTER RATE CALCULATIONS
6 nights = weekly rate ÷ 7 x 6
5 nights or less = weekly rate ÷ 6 x 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
Barefoot Cowboy 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
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!
