BAREFOOT COWBOY (58ft) – Book Island Cruise

BAREFOOT COWBOY

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  • Amenities Details
  • 7-Night Rates
  • Availability
  • Specifications
  • #

    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
     

  • #

    Offered via rendezvous only

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: $33,000
  • 3 Guests: $33,500
  • 4 Guests: $34,000
  • 5 Guests: $34,500
  • 6 Guests: $35,000
  • 7 Guests: $35,500
  • 8 Guests: $36,000
  • 9 Guests: $36,500
  • 10 Guests: $37,000
Season Name: Summer 2027    Currency: USD    Terms: (Caribbean Terms) Inclusive
  • 2 Guests: $33,000
  • 3 Guests: $33,500
  • 4 Guests: $34,000
  • 5 Guests: $34,500
  • 6 Guests: $35,000
  • 7 Guests: $35,500
  • 8 Guests: $36,000
  • 9 Guests: $36,500
  • 10 Guests: $37,000
Season Name: Additional Rates & Notes    Currency: USD    Terms: (Caribbean Terms) Inclusive
    Additional Rate Details: #

    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:

    Check Charter Availability by Month

    Booked Hold Unavailable

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    Yacht layout

    Yacht Layout

    Specifications

    #Pax:10
    Length:58 ft.
    Beam:27
    Draft:5.7
    Make:Leopard
    # Cabins:5
    Cabin Configuration:4
    Showers:5
    Tubs:
    Wash Basins:5
    Heads:
    Elec. Heads:5
    TP in Heads: No
    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:

    Yacht Haven Grand
    Other Pick-up:
    Turn-around: 48 hours
    C. Permit: 1
    License: 1
    MCA Compliance:

    Amenities

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

    Water Sports

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

    Price details
    • Year Built 2015
    • Length 58 ft.
    • Designer Leopard
    • Cabins 5
    • Maximum Guests 10
    • Starting From $27,200

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

    Book Now#

    Got a Question? We’ve Got Answers.

    Contact Us Today

    Meet our Crew

    Crew Member Roy Rucker
    Crew Member Natalie Rucker
    Crew Member Pete

    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.

    Read More
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    watch crew interview #

    Onboard Dining

    Main Dish
    Dish 1
    Dish 2
    Dish 3
    Dish 4
    Dish 5
    Dish 6
    Dish 7

    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

    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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