BAREFOOT COWBOY

$33,000 - $33,000 / per Week

LAYOUT

SPECIFICATIONS

FEATURES

Learn more about BAREFOOT COWBOY

  • Accommodations
  • Entertainment
  • Guest Amenities
  • 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.

  • Fish Permit BVI Permit in Process

  • Ac Full

Your Crew

CAPTAIN Roy Rucker & MATE/CHEF Natalie Rucker


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.

×

Rates

Season 2 Pax 4 Pax 6 Pax 8 Pax 10 Pax
Additional Rates & NotesN/AN/AN/AN/AN/A
Winter 2026 to 2027$33,000$34,000$35,000$36,000$37,000
Summer 2027$33,000$34,000$35,000$36,000$37,000
Winter 2027 to 2028$33,000$34,000$35,000$36,000$37,000
Summer 2028$33,000$34,000$35,000$36,000$37,000

BAREFOOT COWBOY 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

×

Write a Review

Post Charter Survey

  • Home Sweet Home!

    Now that you're back, we would love to hear your feedback on your charter vacation, especially while it's fresh in your mind.
    Vacations fade. That's why we need to have so many of them. 😊