BAREFOOT COWBOY - CHARTER SMARTER

BAREFOOT COWBOY

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Yacht Logo

Nothing compares to cruising the sea aboard the Leopard 58. Barefoot Cowboy has a spacious, split-level floor plan. On the main deck you will find two cabins opening to a forward cockpit. Three cabins below, all with private en- suite baths. All cabins are air-conditioned. Inside you will discover a well appointed galley. Meals can be enjoyed inside with wrap around seating for 10. The yacht also comes complete with a 46” flat screen TV/DVD player, onboard WiFi, Apple TV, CD stereo with MP3 connection. Venture up to the enormous fly bridge and captain from the helm station with a 360-degree vantage point. The fly bridge includes stylish lounge seating with an electric grill, wet bar and refrigerator. This is the place to gather and enjoy cocktails with friends. The fly bridge is also wired for sound. Feel free to dance! The best place for al fresco dinning is on our aft deck. Barefoot Cowboy has a beautiful teak table for 10 and a view of the islands you will never forget. She is the perfect escape for large groups up to 10 guests.

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    2 Stand Up Paddle Boards
    1 Bote 2 Person Inflatable Kayak
    2 Bote Floating Chairs
    Megachill
    Noodles
    Underwater Camera
    Snorkeling Gear
    Tubes
    1 Subwing
    2 Fishing Rods
    Onshore Games.
    Dinghy Boarding Ladder

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    Offered via rendezvous only

Season Name: Summer 2025    Currency: USD    Terms: (Caribbean Terms) Inclusive
  • 2 Guests: $32,000
  • 3 Guests: $32,500
  • 4 Guests: $33,000
  • 5 Guests: $33,500
  • 6 Guests: $34,000
  • 7 Guests: $34,500
  • 8 Guests: $35,000
  • 9 Guests: $35,500
  • 10 Guests: $36,000
Season Name: Winter 2025 to 2026    Currency: USD    Terms: (Caribbean Terms) Inclusive
  • 2 Guests: $32,000
  • 3 Guests: $32,500
  • 4 Guests: $33,000
  • 5 Guests: $33,500
  • 6 Guests: $34,000
  • 7 Guests: $34,500
  • 8 Guests: $35,000
  • 9 Guests: $35,500
  • 10 Guests: $36,000
Season Name: Summer 2026    Currency: USD    Terms: (Caribbean Terms) Inclusive
  • 2 Guests: $32,000
  • 3 Guests: $32,500
  • 4 Guests: $33,000
  • 5 Guests: $33,500
  • 6 Guests: $34,000
  • 7 Guests: $34,500
  • 8 Guests: $35,000
  • 9 Guests: $35,500
  • 10 Guests: $36,000
Season Name: Winter 2026 to 2027    Currency: USD    Terms: (Caribbean Terms) Inclusive
  • 2 Guests: $32,000
  • 3 Guests: $32,500
  • 4 Guests: $33,000
  • 5 Guests: $33,500
  • 6 Guests: $34,000
  • 7 Guests: $34,500
  • 8 Guests: $35,000
  • 9 Guests: $35,500
  • 10 Guests: $36,000
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 • 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 2025 / 2026 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:USVI / BVI

Summer Operating Area:Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)

Winter Base Port:USVI / BVI

Winter Operating Area: Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI)

Location Details:

Check Charter Availability by Month

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July 2025

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Specifications

#Pax:10
Length:58
Beam:27
Draft:5.7
Make:Leopard
# Cabins:5
Cabin Configuration:4
Showers:5
Tubs:
Wash Basins:5
Heads:5
Elec. Heads:5
TP in Heads:
Helipad: No
Jacuzzi: No
A/C:Full
Engines/Generators:2, 110hp Yanmar engins, 1 22kw Norhtern Lights Generator
Year Built:2015
Cruising Speed:10
Max Speed:20

Locations

Pref. Pick-up:

YHG | AYH STT

Other Pick-up: BVI
Turn-around: 48 hrs preferred, Inquire for
C. Permit: 1
License: 1
MCA Compliance:

Amenities

Salon Stereo: Yes
Salon TV: No
Sat Tv: No
Device Hookups:
Hammock:Yes
Windscoops:
Kosher:No
Bimini:
Special Diets:Yes
Deck Shower: Yes
BBQ: Yes
# Dine In:10
Hairdryers:Yes
Nude:Inq
Guests Smokes: Sugar Scoops only
Pets Aboard: Yes
Guest Pets: No
Children Ok: Yes
Minimum Age:Any Age
Gym/Exercise: No
Elevators: No
Wheel Chair Access: No
Inverter:
Voltages:220/120v
Water Maker: Yes
Water Cap:
Stabilizers: No
Ice Maker: Yes
Internet Access:Onboard WIFI
Sailing Instructions:No

Water Sports

Dinghy hp:50
Dinghy # pax:9
Sailing Dinghy: No
Sea Scooters: No
Water Skis Adult: No
Water Skis Kids: Yes
Wave Runners hp: No
Kneeboard: No
Windsurfer: No
Snorkel Gear:Yes
Tube:Yes
Scurfer: No
Wake Board: No
Kayaks 1 Pax: No
Kayaks (2 Pax): 1
SU Paddle Boards:2
Floating Mats:2
Swim Platform:
Boarding Ladder (Loc/Type):
Beach Games:
Fishing Gear: Yes
Gear Type:2 Casting
Rods:2
Fishing Permit: BVI Permit in Process
U/Water Camera: No
U/Water Video:
Sea Bobs: No
Kite Boarding: No
Kite Boarding Details:

Other Toys

2 Stand Up Paddle Boards
1 Bote 2 Person Inflatable Kayak
2 Bote Floating Chairs
Megachill
Noodles
Underwater Camera
Snorkeling Gear
Tubes
1 Subwing
2 Fishing Rods
Onshore Games.
Dinghy Boarding Ladder

Price details
  • Year Built 2015
  • Length 58 ft.
  • Designer Leopard
  • Cabins 5
  • Maximum Guests 10
  • Starting From $26,367

*2 Guests, 5 Nights with Half-Board Meal Package

Got a Question? We’ve Got Answers.

Natalie Rucker

Desserts

Main Dish
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Dish 5
Dish 6

Guest Testimonials

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!

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