BAREFOOT COWBOY
Barefoot Cowboy Yacht Charter
Set sail on Barefoot Cowboy, a magnificent Leopard 58 catamaran that offers the perfect balance of luxury, adventure, and relaxation. Designed for comfort and style, this yacht boasts a spacious split-level floor plan, ensuring ample room for guests to unwind while taking in breathtaking ocean views. Whether you’re indulging in gourmet meals, soaking up the sun on the flybridge, or enjoying a sunset cocktail with friends, Barefoot Cowboy promises an unforgettable charter experience.
Unmatched Comfort & Accommodations
Accommodating up to 10 guests, Barefoot Cowboy features four queen cabins and a versatile twin cabin that can be converted into a king upon request. Each cabin is fully air-conditioned and equipped with a private en-suite bath, ensuring ultimate comfort and privacy. Thoughtfully designed interiors include a well-appointed galley, wrap-around seating for communal dining, and stylish furnishings that create a welcoming atmosphere for guests.
Elevated Onboard Experience
The yacht’s expansive flybridge is the perfect spot to enjoy 360-degree panoramic views while cruising through stunning island destinations. This space is designed for entertainment, featuring lounge seating, an electric grill, a wet bar, and a refrigerator to keep refreshments at hand. The flybridge is also wired for sound, making it the ideal place for music, dancing, and socializing under the stars. The aft deck provides another prime location for al fresco dining, complete with a beautifully crafted teak table for 10, offering an unbeatable backdrop of turquoise waters and island landscapes.
Advanced Technology & Upgrades
Barefoot Cowboy is outfitted with top-of-the-line electronics, including a RayMarine chart plotter, depth and wind monitoring systems, autopilot, and VHF radio. The main salon is equipped with a 46” Samsung LED TV, Bose surround sound, Apple TV, WiFi, and a Fusion entertainment system with Bluetooth connectivity, ensuring seamless entertainment throughout the journey.
Recent refits in 2023 and 2024 have enhanced the yacht’s amenities, including a newly installed water maker, solar panels, a powerful generator, and an upgraded air conditioning system. Additional upgrades include a new flybridge fridge, ice maker, and enhanced enclosures, ensuring a luxurious and seamless onboard experience.
Secure Your Exclusive Getaway
Why wait to embark on the adventure of a lifetime? Barefoot Cowboy offers a one-of-a-kind luxury yacht charter experience designed to create lasting memories. Book your dream escape today and cruise the open seas in unparalleled style and comfort!
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.
| Accommodations | |
|---|---|
| Cabins: | 5 |
| Queen: | 4 |
| Single Cabins: | 1 |
| Showers: | 5 |
| Electric Heads: | 5 |
| Engine Details | |
|---|---|
| 2, 110hp Yanmar engins, 1 22kw Norhtern Lights Generator | |
| Fuel Consumption: | - |
| Cruising Speed: | 10 |
| Max Speed: | 20US Gall/Hr |
| Details | |
|---|---|
| Type: | Cat |
| Beam: | 27 Feet |
| Draft: | 5.7 Feet |
| Pax: | 10 |
| Refit: | 2023 |
| YearBuilt: | 2015 |
| Builder: | Leopard |
| JetSkis: | No |
| Flag: | US |
| RegNum: | VI7840TC |
| Engines: | 2, 110hp Yanmar engins, 1 22kw Norhtern Lights Generator |
| Jacuzzi: | No |
| A/C: | Full |
| Locations | |
|---|---|
| Winter Area: | Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI) |
| Summer Area: | Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI) |
| Pick Up Locations | |
|---|---|
| Pref. Pick-up: | - |
| Other Pick-up: | - |
| Amenities | |
|---|---|
| Salon Tv/VCR: | No |
| Salon Stereo: | No |
| Sat Tv: | - |
| Camcorder: | No |
| Books: | No |
| Board Games: | No |
| Deck Shower: | No |
| Water Maker: | yes |
| Special Diets: | Yes |
| Kosher: | No |
| BBQ: | No |
| Minimum Age: | Swim Safe |
| Inverter: | No |
| Voltages: | - |
| Water Maker: | yes |
| Ice Maker: | - |
| Sailing Instructions: | - |
| Internet Access: | - |
| Hairdryers: | Yes |
| Guests Smokes: | Sugar Scoops only |
| Crew Smokes: | No |
| Pets Aboard: | No |
| Hammock: | No |
| Water Sports | |
|---|---|
| Dinghy size: | No |
| Dinghy hp: | - |
| Water Skis Adult: | No |
| Water Skis Kids: | No |
| Jet Skis: | No |
| Kneeboard: | No |
| Windsurfer: | No |
| Snorkel Gear: | No |
| Tube: | No |
| Scurfer: | No |
| Wake Board: | No |
| Kayaks 1 Pax: | No |
| Kayaks (2 Pax): | No |
| Floating Mats: | No |
| Swim Platform: | No |
| Boarding Ladder (Loc/Type): | No |
| Sailing Dinghy: | - |
| Beach Games: | No |
| Fishing Gear: | No |
| Gear Type: | - |
| Rods: | - |
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.
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
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
Take care,
Emily & Justin
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
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
Kathy
Clare
10% will be discounted from the standard charter rate for charters started and completed between 11/18/23 and 12/17/23 – including Thanksgiving charters. The charter must be booked after 10/03/23, have a minimum of 5 nights and cannot be in conjunction with any other specials for the discount to apply.
Christmas charters are offered in the Virgin Islands at the STANDARD seasonal rate. Availability restrictions apply. The charter must be booked and completed before 1/07/2024. This special cannot be combined with other offers.
| Season | 2 PAX | 3 PAX | 4 PAX | 5 PAX | 6 PAX | 7 PAX | 8 PAX | 9 PAX | 10 PAX | 11 PAX | 12 PAX |
|---|---|---|---|---|---|---|---|---|---|---|---|
| Additional Rates & Notes | |||||||||||
| Winter 2026 to 2027 | $33,000 | $33,500 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 | $36,500 | $37,000 | ||
| Summer 2027 | $33,000 | $33,500 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 | $36,500 | $37,000 | ||
| Winter 2027 to 2028 | $33,000 | $33,500 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 | $36,500 | $37,000 | ||
| Summer 2028 | $33,000 | $33,500 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 | $36,500 | $37,000 |
Unless otherwise specified-Caribbean Standard All-Inclusive Charters include the following:
- Standard check-in/check-out of 12pm
- Light daily housekeeping
- Breakfast, lunch, canapés/afternoon tea, dinner and snacks
- Standard ship’s bar: vodka, gin, rum, whiskey, tequila, triple sec, mixers, local beers, table wine and water/coffee/tea and soft drinks
- Stereo with MP3/iPhone connection with indoor/outdoor speakers; 3G/4G Wi-Fi access point
- Snorkeling equipment, fishing gear, kayaks, dingy tender with outboard motors
- Water toys such as floating islands, and air mattresses
- Separate bathroom and living quarters for crew
- Reputable and licensed crew who have local knowledge of waters and are able to adjust menus based on guest’s preferences and dietary restrictions
- Operating expenses including: use of air conditioning, fuel, water, sailing permits/taxes, local taxes and crew wages
What Is Not Included in Standard All-Inclusive Charters:
- Gratuity for crew. Gratuity is at guest discretion and is typically between 15-20%
- Meals and beverages at restaurants and bars
- Rendezvous diving, ASA sailing certification courses and any other offshore excursions
- Premium wines and spirits
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
X
Available
X
Booked
X
Hold
X
Unavailable
- : Cat
- : 27 Feet
- : 5.7 Feet
- : 10
- : 2023
- : 2015
- : Leopard
- : 10
- : 20
- : No
- : No
- : Rendezvous Not Included
- : Roy Rucker
- : US
- : VI7840TC
- : 2, 110hp Yanmar engins, 1 22kw Norhtern Lights Generator
| Accommodations | |
|---|---|
| Cabins: | 5 |
| Queen: | 4 |
| Single Cabins: | 1 |
| Showers: | 5 |
| Wash Basins: | 5 |
| Heads: | - |
| Electric Heads: | 5 |
| Engine Details | |
|---|---|
| 2, 110hp Yanmar engins, 1 22kw Norhtern Lights Generator | |
| Fuel Consumption: | - |
| Cruising Speed: | 10 |
| Max Speed: | 20US Gall/Hr |
| Details | |
|---|---|
| Refit: | 2023 |
| Helipad: | No |
| Jacuzzi: | No |
| A/C: | Full |
| Locations | |
|---|---|
| Winter Area: | Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI) |
| Summer Area: | Caribbean Virgin Islands (US/BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (BVI) |
| Pick Up Locations | |
|---|---|
| Pref. Pick-up: | - |
| Other Pick-up: | - |
| Amenities | |
|---|---|
| Salon Tv/VCR: | No |
| Salon Stereo: | No |
| Sat Tv: | - |
| # of Videos: | - |
| # DVDs/Movies: | No |
| # CD's: | No |
| Camcorder: | No |
| Books: | No |
| Board Games: | No |
| Sun Awning: | No |
| Deck Shower: | No |
| Bimini: | No |
| Water Maker: | yes |
| Special Diets: | Yes |
| Kosher: | No |
| BBQ: | No |
| # Dine In: | No |
| Minimum Age: | Swim Safe |
| Generator: | - |
| Inverter: | No |
| Voltages: | - |
| Water Maker: | yes |
| Water Cap: | - |
| Ice Maker: | - |
| Sailing Instructions: | - |
| Internet Access: | - |
| Gay Charters: | Inq |
| Nude: | Inq |
| Hairdryers: | Yes |
| # Port Hatches: | No |
| Guests Smokes: | Sugar Scoops only |
| Crew Smokes: | No |
| Pets Aboard: | No |
| Pet Type: | - |
| Guest Pets: | No |
| Children Ok: | Yes |
| Hammock: | No |
| Windscoops: | No |
| Water Sports | |
|---|---|
| Dinghy size: | No |
| Dinghy hp: | - |
| Dinghy # pax: | - |
| Water Skis Adult: | No |
| Water Skis Kids: | No |
| Jet Skis: | No |
| Wave Runners: | No |
| Kneeboard: | No |
| Windsurfer: | No |
| Snorkel Gear: | No |
| Tube: | No |
| Scurfer: | No |
| Wake Board: | No |
| Kayaks 1 Pax: | No |
| Kayaks (2 Pax): | No |
| Floating Mats: | No |
| Swim Platform: | No |
| Boarding Ladder (Loc/Type): | No |
| Sailing Dinghy: | - |
| Beach Games: | No |
| Fishing Gear: | No |
| Gear Type: | - |
| Rods: | - |
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.
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
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
Take care,
Emily & Justin
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
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
Kathy
Clare
| Season | 2 PAX | 3 PAX | 4 PAX | 5 PAX | 6 PAX | 7 PAX | 8 PAX | 9 PAX | 10 PAX |
|---|---|---|---|---|---|---|---|---|---|
| Additional Rates & Notes | |||||||||
| Winter 2026 to 2027 | $33,000 | $33,500 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 | $36,500 | $37,000 |
| Summer 2027 | $33,000 | $33,500 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 | $36,500 | $37,000 |
| Winter 2027 to 2028 | $33,000 | $33,500 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 | $36,500 | $37,000 |
| Summer 2028 | $33,000 | $33,500 | $34,000 | $34,500 | $35,000 | $35,500 | $36,000 | $36,500 | $37,000 |
Unless otherwise specified-Caribbean Standard All-Inclusive Charters include the following:
- Standard check-in/check-out of 12pm
- Light daily housekeeping
- Breakfast, lunch, canapés/afternoon tea, dinner and snacks
- Standard ship’s bar: vodka, gin, rum, whiskey, tequila, triple sec, mixers, local beers, table wine and water/coffee/tea and soft drinks
- Stereo with MP3/iPhone connection with indoor/outdoor speakers; 3G/4G Wi-Fi access point
- Snorkeling equipment, fishing gear, kayaks, dingy tender with outboard motors
- Water toys such as floating islands, and air mattresses
- Separate bathroom and living quarters for crew
- Reputable and licensed crew who have local knowledge of waters and are able to adjust menus based on guest’s preferences and dietary restrictions
- Operating expenses including: use of air conditioning, fuel, water, sailing permits/taxes, local taxes and crew wages
What Is Not Included in Standard All-Inclusive Charters:
- Gratuity for crew. Gratuity is at guest discretion and is typically between 15-20%
- Meals and beverages at restaurants and bars
- Rendezvous diving, ASA sailing certification courses and any other offshore excursions
- Premium wines and spirits
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
