BRITISH VIRGIN ISLANDS · 4 DAYS
4-Day BVI Itinerary: A Crewed Long-Weekend Charter
Four days in the BVI, crewed — Norman Island caves, The Baths, Soggy Dollar at White Bay, the Sir Francis Drake Channel. The short-week BVI itinerary.
58
FT — SAILING CATAMARAN
10
GUESTS
5
CABINS
3
CREW
Summer Cruising
Winter Cruising
From
$32,000
Per Week
10 reviews10 reviews
The Yacht
'Barefoot Cowboy' is a Sailing Catamaran, accommodating up to 10 guests, available for crewed charter.
Barefoot Cowboy Description and Charter Summary Information
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Specifications
At a Glance
- Length
- 58 ft
- Beam
- 27 ft
- Guests
- 10
- Cabins
- 5
- Heads
- 5
- Queen Beds
- 4
- Twin Cabins
- 1
- Year Built
- 2015
- Year Refit
- 2023
Yacht Information
Barefoot Cowboy on Film
Additional yacht details including amenities and standard equipment for Barefoot Cowboy
Explore Barefoot Cowboy
May 1, 2026 – Oct 31, 2026
Summer 2026
$32,000–$36,000 / week
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
Base: St Thomas USVI · Pickup: Yacht Haven Grand
Nov 1, 2026 – Apr 30, 2027
Winter 2026 to 2027
$33,000–$37,000 / week
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
Base: St Thomas USVI · Pickup: Yacht Haven Grand
May 1, 2027 – Oct 31, 2027
Summer 2027
$33,000–$37,000 / week
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
Base: St Thomas USVI · Pickup: Yacht Haven Grand
Rate Notes & Conditions
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
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
Tender
AB for 9ppl with 50hp outboard
1 2-Person Kayak
1 Kids Water Ski
1 Subwing
2 Floating Chairs
Beach Games
Fishing Gear— 2 Casting rods
Fishing Permit— BVI Permit in Process
Floating Mats
Foam Noodles
Kayak (2-person)
Megachill
Snorkel Gear
Stand-up Paddleboards
Tube
Underwater Camera
Water Skis (Kids)
Air Conditioning
Water Maker
BBQ
Board Games
Books
CDs
DVDs
Deck Shower
Dining
Generator— 1 22kw Norhtern Lights Generat
Hair Dryer
Hammock
Ice Maker
Internet/WiFi— Starlink
Salon Stereo
Smoking Allowed— Sugar Scoops only
VCR/DVD
Video
iPod/MP3
Captain
Roy Rucker
American · English
Chef/First Mate
Natalie Rucker
American · English
3rd Mate- Friendly Pup
Pete
Miniature Wirehaired Dachshund · Woof Woof
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
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
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07 / Open Weeks
'Barefoot Cowboy' Availability
Cruising Grounds
Where Barefoot Cowboy voyages
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