A week in the British Virgin Islands aboard Barefoot Cowboy

I’m waking up to another blissful morning aboard Barefoot Cowboy, a luxury sailing catamaran moored somewhere in the British Virgin Islands archipelago, and I have no idea what day it is. Nor do I care. 

Turquoise waves gently rock the vessel from side to side as early morning sunlight streams through our cabin’s windows, inviting us to begin another day in paradise. When my husband and I emerge from our surprisingly comfortable private cabin –– a cozy bedroom featuring a queen bed, ensuite bathroom, and doors leading toward the galley on one end and the bow on the other –– we’re greeted with freshly-brewed coffee and a colorful plate of tropical fruit.  

We head up the stairs to the shaded flybridge, which has become our outdoor living room for the week, to sip coffee and read. We’re surrounded by ocean as far as the eye can see: sapphire seas sparkling in the morning sunlight, emerald islands scattered across the horizon, and pearl-white sails piercing into an impossibly blue sky.  

Barefoot Cowboy’s 10 guests swap swimsuits for real clothes on their way to a Caribbean lobster dinner on Anegada one evening.

I’ve never been on a cruise ship –– by choice –– but this feels like the antithesis of one.  

There are only 10 guests aboard Barefoot Cowboy: my husband, our three kids and me, along with another family of five we’ve traveled with almost every summer since our children were toddlers. Our kids, who range in age from 11 and 18, have grown up taking vacations together which means we have the added bonus of traveling with built-in playmates who are old enough to entertain themselves. Over the course of the week, I rarely see our kids on screens. They snorkel and paddleboard. They kayak to shore and play soccer on the beach. They play cards and dominos. They laugh –– a lot. 

Chef Natalie appears at the top of the stairs to ask if we’d like mimosas (is this a rhetorical question?) as we gather around the outdoor table set for 10 to enjoy the delicious breakfast spread she’s prepared: bagels and lox, cream cheese and jams, scrambled eggs and bacon, and more fresh fruit. We eat every meal al fresco at the shaded stern, with menus customized to our group’s tastes and preferences: breakfasts like blueberry pancakes or eggs Benedict; lunches of yellowfin tuna poke bowls or cheeseburgers; and dinners featuring filet mignon with Caribbean lobster or grilled mahi mahi with mango salsa and coconut rice.  

As soon as our kids finish breakfast, they slather on reef-safe sunscreen, dive into the water, and swim out to the MegaChill, which has become their own private floating pool in the Caribbean. We watch from the boat, sipping mimosas and chatting in the cool trade winds.  

Ultimate relaxation 

This entire week aboard a private yacht, complete with a captain and chef, is about as far removed from my normal reality as possible. And I’m relishing every serene second. 

This is the first family vacation I’ve ever taken where there’s no grocery shopping or meal planning to do. No tables to clear. No dishes to wash. It’s all done for us. We don’t stress about where to go or what to do, either. Each day brings a different island and a new adventure, and we don’t have to worry about the usual logistics of getting there. I honestly can’t remember a time I’ve felt this relaxed. And I know I’ve never taken a family vacation that was so completely void of stress and full of carefree fun. 

I’m fully embracing my new and unfamiliar role as “vacation mom,” who, coincidentally, is loving the temporary reprieve from her normally Type-A, worry-prone, routine-driven self. (I think my husband and kids really like her a lot, too).  

Texans Captain Roy and Chef Natalie Rucker, along with their dog Pirate Pete, make guests feel at ease aboard their Virgin Islands home, Barefoot Cowboy. Photo by Mauri Elbel

Barefoot Cowboy’s Crew 

Vacation mom was made possible by two people: Roy Pat and Natalie Rucker, native Texans who have made Barefoot Cowboy their Virgin Islands home. Today, the couple along with First Mate Pete, their adorable miniature wirehaired dachshund with a personality much bigger than his stature, make a living by taking guests on unforgettable charter vacations.  

At the helm of Barefoot Cowboy is Captain Roy, a Texas-born-and-raised cowboy who grew up working on ranches and rodeoing long before owning and operating a boat. His easygoing competence brings a capable presence to the boat as he expertly navigates us from one island destination to the next. As he steers us through the Caribbean for the week, not a single worry crosses our minds. Natalie, a retired optician turned self-taught chef, has a charismatic charm that puts her guests at ease in the same way, always ensuring no one gets hungry or thirsty. I’m still in awe of how she makes preparing multi-course meals for 10 people in a tiny kitchen on a rocking boat look effortless.  

Pirate Pete is a miniature wirehaired dachshund aboard Barefoot Cowboy whose official jobs include keeping spirits high and making sure any dropped food on deck is cleaned up immediately. Photo by Mauri Elbel

Booking the boat 

I’ve dreamed of taking a BVI sail trip with my family for years. Having lived and worked on St. John in my 20s and returning almost annually with my family ever since, I’m familiar with the U.S. and British Virgin Islands. But the idea of spending a week sailing through the islands came with a couple minor obstacles: One, we don’t know how to sail. And, two, we know almost nothing about boats (other than we like to be on them).  

RELATED: St. John: A perfect week in paradise

Earlier this year, I became more serious about the idea of a sailing vacation and stumbled upon Charter Smarter, which operates as one-stop yacht-vacation matchmaker and concierge. Charter Smarter, which has more than 70 luxury yachts to choose from, took the uncertainty out of booking by helping me sort through the dizzying array of yachts, crews, itineraries and pricing options to match us with a catamaran that best fit our dates, budget and group. 

Charter Smarter proved invaluable throughout the entire planning process, from matching us with the right boat and crew to ensuring we had a personalized itinerary curated to our tastes and preferences.  

They even handled the unglamorous details like helping us with travel insurance, understanding the contract, and travel logistics. For example, because we were already staying on St. John, booking with Barefoot Cowboy afforded us the added bonus of being picked up and dropped back off on the island, eliminating the hassle of ferrying back and forth between St. Thomas or Tortola. And everything was fully all-inclusive, from having a professional captain and chef onboard to all meals and beverages, custom fees and water toys. 

The Baths on Virgin Gorda, a famous national park in the British Virgin Islands, features giant granite boulders, hidden tidal pools, and scenic sea caves you can wander through. Photo by Mauri Elbel

Island hopping through the BVI’s 

Being on Barefoot Cowboy was like staying alone at an all-inclusive luxury resort with your best friends. Only better because a boat offers something even the most exclusive resort experience can’t replicate: your accommodations move with you.  

Every morning, we woke up somewhere new. We could jump off the back of the boat before breakfast. We could spend an entire afternoon swimming and snorkeling. We could take the dinghy ashore for a fancy island dinner or visit beaches that can only be reached via the sea.  

We spent the week visiting some of my favorite British Virgin Islands. But even when boating from one island to another, the journey was part of the fun –– we played games, read, drank, laughed and sunbathed our way from point A to B. 

After spending a night moored in Caneel Bay on St. John and clearing Customs in Tortola, our first stop was Norman Island. Here, we snorkeled around the Caves, ducking in and out of rocky openings and getting a glimpse into the colorful underwater world that has made the area a top snorkeling destination. We ended the day on the infamous Willy T –– the massive multi-level pirate ship anchored in a protected cove off Norman Island where boaters go to sip a strong rum punch and leap from the top deck into the ocean. 

Jumping off the upper deck of the Willy T off Norman Island in the BVI is a legendary Caribbean tradition and rite of passage. Photo by Mauri Elbel

The following morning, we sailed to Virgin Gorda to explore The Baths, one of my favorite spots in the entire Caribbean. Whether it’s your first or fifteenth time visiting The Baths, there’s nothing quite as magical as wandering through these gargantuan granite boulders that create natural grottos and secluded saltwater pools. Wooden steps and rope handrails guide you along the cavernous trail to Devil’s Bay, a National Park beach with sugary white sand where you can sip a frozen rum drink and wade in the crystal-clear water.   

RELATED: Travel to Tortola

From there, we made our way to the northeastern tip of Virgin Gorda’s North Sound to while away the afternoon at the exclusive Bitter End Yacht Club before enjoying a fancy dinner at Saba Rock, a tiny acre-and-a-half island resort with world-class culinary offerings. That night, moored off Saba Rock under the glow of a full moon, the kids decided to make the cozy beanbags scattered on the bow of the boat their beds for the evening and we found them still sound asleep in the mid-morning sunlight. 

Thankfully, the Caribbean seas were calm as could be during our mid-summer trip, and we were able to make a trip all the way to Anegada. Boating toward Anegada, you don’t see much –– she’s a flat, low-lying coral and limestone rarity in a Caribbean sprinkled with volcanic islands. Anegada’s highest point is just 28 feet, and she features numerous salt ponds frequented by pink flamingos and endless stretches of deserted talcum shores lapped by turquoise water. When we arrived on Anegada, the Ruckers rented an open-air taxi truck to drive us around to some of their favorite Anegada spots, from deserted beaches to pour-your-own honor bars.      

There’s no better place to eat Caribbean lobster than Anegada, the lobster capital of the Caribbean, thanks to its huge barrier reef and shallow waters that teem with plus-sized spiny lobsters. We feasted on delicious Caribbean lobster that night at Potters By The Sea, but in the past, we’ve also enjoyed barbecued lobster on the beachfront of Anegada Reef Hotel. This tiny island is inhabited by only a few hundred residents, and restaurants here require lobster dinner requests in advance. 

Hydrating with coconut water from freshly cracked coconuts at Hendo’s Hideout on Jost Van Dyke. Photo by Mauri Elbel

Jost Van Dyke provided a fairytale finale to our week in the BVI. If too-blue-to-be-true waves lapping a pillowy slope of white sand fringed by palm trees and thatched-roof, swim-up beach bars sounds like your version of heaven, then you’ll also be a fan. We slept in the protected waters of Great Harbour, lunched on brick oven pizzas at Alice’s Restaurant and Bar, and took the short trek over to the livelier side of White Bay to sip painkillers at Soggy Dollar, play beach volleyball at Hendo’s Hideout, and cool off in the stunning bay.  

The best vacation 

When we sailed back to St. John at the end of our trip, I realized how much I was dreading leaving Barefoot Cowboy. But for me, I knew I was going to miss so much more than the beautiful boat. I was going to miss the absence of decisions and schedules, and the flexibility to take each day as it comes. 

Our week aboard Barefoot Cowboy gave us the privacy and personal service of a luxury resort, the adventure of an island-hopping expedition, and the freedom to experience total relaxation. This was the first family vacation where I genuinely felt like I had gotten away, rather than simply relocated all of my usual responsibilities to a new, prettier place.  

There’s something different about experiencing the Caribbean this way, when the islands become your backyard. One day, we’re snorkeling the Caves of Norman Island and watching our kids take their inaugural leap off the Willy T, and the next morning, we’re wandering through The Baths and dining at the exclusive Saba Rock. One night we’re eating lobster on Anegada and the next morning, we’re sipping painkillers for breakfast on Jost Van Dyke. 

By the end of the week, I had forgotten what day it was. My phone and laptop spent the whole trip in my suitcase. My kids had spent hours in the water with lifetime friends instead of zoning out mindlessly in front of a screen. And I had somehow managed to go seven whole days without planning a single dinner.

That, more than anything, felt like a true vacation. A complete reset. And yes, we will do this again.