Big news for Caribbean cruisers: Nanny Cay Marina on Tortola has begun construction on a major expansion that will add a third marina basin, increase haulout capacity and create new berthing for the growing fleet of large catamarans and luxury yachts cruising the Caribbean.

The development includes a custom Marine Travelift designed for 60- to 80-foot multihulls, 112 new slips for catamarans, private boats and yachts up to 165 feet, and expanded yard space. The investment is expected to exceed $30 million and will roll out over three years.

“This expansion reflects our ongoing commitment to improving facilities for the BVI’s marine community and strengthening Nanny Cay’s position as the heart of Caribbean yachting,” said Cameron McColl, chairman of Nanny Cay. He noted that increased lift capacity and berthing will help serve “the growing number of large catamarans and superyachts operating in the region.”

General Manager Miles Sutherland-Pilch said the demand has been clear. “We were seeing increasing demand from larger multihulls and monohulls, and this project was designed to meet that need,” he said. “The new lift and berths will allow us to handle more vessels efficiently and safely.”

BVI Premier Dr. Natalio Wheatley called the expansion the first phase of a broader redevelopment plan for the resort and marina. He said the project represents “a declaration of confidence in our economy, our people and in the Virgin Islands as a premier destination for tourism, maritime excellence and sustainable growth.” Wheatley also highlighted the plan’s workforce impact, citing 91 new jobs and a training partnership with H. Lavity Stoutt Community College.

Along with expanded marine services, the project includes customer amenities like a new beach, pool, restaurants, retail village and a dedicated classroom for youth maritime programs. Nanny Cay will also continue to serve as home base for the BVI Spring Regatta and Sailing Festival, which will celebrate its 53rd running in 2026.

With the BVI continuing to attract passagemakers, charter guests and long-range cruisers, the expansion aims to keep pace with the next generation of cruising platforms while reinforcing the territory’s reputation as one of the Caribbean’s premier boating destinations.

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For the fifth year in a row, The Moorings has been recognized with Tripadvisor’s Travelers’ Choice Award in the “Things To Do” category for its charter operations in the British Virgin Islands. The award places The Moorings among the top 10 percent of attractions worldwide based on consistently strong guest reviews.

“Winners are calculated based on the quality and quantity of the millions of reviews, opinions, and ratings collected on Tripadvisor,” the company explains. “With over 8.7 million businesses listed on Tripadvisor, these awards are a true testament to the outstanding service and quality that winners consistently provide to their guests.”

The recognition comes as The Moorings’ BVI base has undergone significant transformation in recent years. Following the devastation of Hurricane Irma in 2017, the company invested in a comprehensive rebuild of its flagship location. Improvements include new docks, a renovated hotel, an on-site supermarket, and a refreshed fleet featuring the latest cruising catamarans and monohulls.

“We are thrilled to have been awarded this award once again,” says Ian Pedersen, Senior Marketing Manager for The Moorings. “It is a testament to the hard work that has gone into rebuilding our flagship destination in the past few years, and a validation that the changes we have implemented are having the desired positive impact for our guests.”

With more than five decades of charter expertise, The Moorings remains one of the most recognized names in global yacht chartering. For many sailors, the British Virgin Islands continue to represent a quintessential cruising ground, with steady trade winds, protected anchorages, and short passages between islands—an ideal setting for a first-time or repeat charter vacation.

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When Captain Glenn Shephard stepped aboard a Moorings catamaran in the British Virgin Islands earlier this year, it wasn’t just another sailing trip. It was the start of a new chapter. Known to many from Bravo’s Below Deck Sailing Yacht, Shephard has built a career on calm command and deep sailing expertise. Now, as The Moorings’ first official brand ambassador, he’s helping usher in a new era of accessible, experience-driven yacht chartering—starting in one of the world’s most iconic cruising grounds.

The British Virgin Islands, Revisited

For Shephard, the BVI are familiar territory. He’s visited these waters many times before, both professionally and personally. This trip, however, marked his first under The Moorings’ banner, a company he describes as raising the bar in both service and vessel quality. Sailing a Moorings 4200, he revisited favorite anchorages and discovered a few new ones too.

It’s not hard to understand the BVI’s appeal. Steady trade winds, short hops between islands and a mix of bustling marinas and quiet coves make it one of the most forgiving and rewarding charter destinations on the planet. Even veteran sailors like Shephard find something new each time. From the distinctive granite formations of The Baths to the legendary scene at the Soggy Dollar Bar, the BVI offer a blend of natural beauty and laid-back charm that’s hard to match.

From Monohull to Multihull

Though he’s spent much of his sailing life on monohulls, including superyachts and racing sloops, Shephard came away from his Moorings 4200 charter impressed. The 42-foot, three-cabin catamaran offered the kind of stability and comfort that’s winning over more and more sailors, especially those chartering with friends or family.

With a wide beam and generous deck space, the cat provided ample room to relax, cook and entertain without anyone stepping on each other’s toes. Below deck, the owner’s suite occupied the entire starboard hull. Shephard likened it more to a guest stateroom on a superyacht than a typical charter cabin. The boat also handled well under sail, moving confidently at 8–9 knots and performing better upwind than he expected for a cruising cat. It’s easy to see why models like this are becoming a staple in the modern charter fleet.

Service That Makes a Difference

While Shepard was impressed by the boat, it was the support behind it that really sparkled. Chartering with The Moorings gave Shephard a chance to experience the company from a customer’s point of view. The base staff in Tortola made the transition from dock to open water seamless, and a minor maintenance issue mid-charter was resolved within the hour. That level of service is something not every charter company can promise, let alone deliver.

It’s these kinds of details that turn a good trip into a great one. For seasoned sailors used to solving every problem themselves, responsive support is a welcome change of pace. For newer charterers, it’s the difference between stress and confidence.

From Television to Tenders

Shephard’s television fame didn’t go unnoticed during the trip. While he’s more accustomed to low-key recognition in European marinas, the BVI proved a bit more lively. Fellow cruisers and fans of the show often stopped to say hello, turning dinghy docks into impromptu meet-and-greets. For Shephard, the most meaningful connections were with other sailors who understood firsthand the joy and challenge of life at sea.

Though he’s now a public figure, Shephard remains grounded in his sailing roots. He’s crossed the Atlantic more than 20 times, holds a UK Master 3,000-ton license and has logged time aboard everything from America’s Cup contenders to some of the world’s largest private sailing yachts. That experience gives weight to his endorsements and lends authenticity to his new partnership with The Moorings.

Charting New Waters

The collaboration between Shephard and The Moorings makes sense: both are rooted in deep sailing expertise, and both are looking toward the future. For The Moorings, that future includes expanding the reach of yacht chartering to a broader, more diverse audience—one that might be discovering sailing for the first time through a TV show, a travel blog or a vacation photo shared online.

Having Shephard as an ambassador helps bridge the gap between seasoned sailors and newcomers. His calm, practical approach and decades of experience make the idea of chartering more approachable. As someone who genuinely enjoys time on the water—whether it’s on a superyacht or a 42-foot cat—he’s well positioned to inspire a new generation of sailors to take the helm.To book a yacht charter with The Moorings yourself, visit moorings.com or speak to a vacation planner directly by calling 866-428-5080.

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Tortola: Hidden Treasures on the Main Island

As the BVI’s largest and most populated island, Tortola serves as the gateway to the archipelago. Beyond provisioning and preparation, this island offers distinctive experiences for those willing to take a deeper look.

Soper’s Hole presents a picturesque anchorage framed by pastel buildings with characteristic white-gingerbread trim. This west end harbor combines practical amenities with authentic charm. Sailors can stock up on essentials while enjoying fresh seafood at local establishments. The colorful architecture creates a postcard-worthy backdrop for your anchorage.

Cane Garden Bay might appear on standard itineraries, but its protected waters and vibrant local scene make it worth exploring differently. Myett’s Garden Inn serves just-caught seafood mere steps from the turquoise water, while Quito’s Gazebo pulses with reggae rhythms as the sun sets. Even Jimmy Buffett has been known to drop anchor here, drawn by the bay’s perfect blend of protection and personality.

For those seeking elevation after days at sea level, Sage Mountain National Park offers hiking trails leading to the highest point in the BVI. The ascent rewards sailors with panoramic views of the entire archipelago—a perspective that transforms your understanding of the sailing grounds below and provides extraordinary photo opportunities.

Anegada: The Coral Outlier

Unlike its volcanic sisters, Anegada stands apart as the only coral island in the chain, characterized by its nearly flat elevation and striking coral reefs. This 11-mile island, requiring a two-and-a-half-hour sail from Virgin Gorda, rewards intrepid sailors with experiences well worth the journey.

Cow Wreck Beach epitomizes the solitude many sailors dream of, with miles of walkable shoreline where you might not encounter another soul. The beach’s namesake bar offers that timeless Caribbean atmosphere—a place to enjoy a cold drink while gazing at waters so clear they seem unreal. Here, time slows to the gentle rhythm of lapping waves.

For underwater enthusiasts, Horseshoe Reef—the Eastern Caribbean’s third-largest continuous reef—presents an aquatic wonderland. Eagle rays, Atlantic spadefish and permit fish dance through vibrant coral formations, creating an underwater spectacle that rivals any on land. The protected waters make for excellent snorkeling right off your boat.

November visitors are treated to the Anegada Lobster Festival, held over American Thanksgiving weekend. This island-wide culinary celebration combines creative seafood preparations with activities like scavenger hunts, offering a unique way to experience local culture and cuisine in a festive atmosphere.

Virgin Gorda: Beyond The Baths

While The Baths National Park rightfully draws visitors to Virgin Gorda with its impressive basalt boulders creating magical grottoes and tunnels, the island also harbors quieter treasures just waiting to be discovered.

Spring Bay sits just east of The Baths but receives a fraction of the visitors. The sprawling beachline features the same awe-inspiring granite boulders as its famous neighbor, creating a sense of peaceful grandeur without the crowds. The soft white sands, calm waters and swaying palm trees make it an idyllic spot to unwind. Snorkelers will delight in schools of colorful fish darting around delicate coral formations just offshore.

Across the channel from The Baths lies Fallen Jerusalem, an uninhabited islet where nature rules undisturbed. Approaching its shores reveals towering cliffs draped with vibrant greenery framing pristine beaches. The island’s captivating underwater caves and grottoes offer snorkelers and divers exploration opportunities in blissful solitude. As a protected marine sanctuary, its waters teem with well-preserved marine life, creating a sustainable underwater wilderness.

Top of the Baths Restaurant provides a strategic vantage point for taking in Virgin Gorda’s geological wonders while enjoying grilled lobster and a well-earned cocktail. The elevated perspective gives sailors a new appreciation for the island’s unique topography while offering a respite from the midday heat.

Jost Van Dyke: Simple Pleasures, Profound Memories

This small island off Tortola’s western shore has gained fame for its beach bars, but Jost Van Dyke offers so much more for sailors seeking authentic experiences.

The Soggy Dollar Bar on White Bay might be known for originating the famous Painkiller cocktail, but the bay itself provides one of the most protected overnight anchorages in the region. Staying beyond the day-tripper hours reveals a different, more serene side of this popular spot.

Sandy Cay, a tiny uninhabited island near Jost, represents the quintessential desert island experience. This spit of land with soft sand and palm forest offers the perfect setting for beach games, picnics, or simply reveling in having a slice of paradise temporarily to yourself.

The Atlantic side of Jost offers dynamic reefs for scuba enthusiasts seeking more challenging dives away from beginner sites. These less-visited diving locations showcase a different aspect of BVI marine life, with dramatic drop-offs and more varied sea creatures adapted to stronger currents.

With three distinct overnight anchorages, Jost Van Dyke invites sailors to linger and experience the island’s natural rhythms—from tranquil mornings with coffee on deck to starlit evenings where the only sounds are waves against the hull and distant music from shore.

Finding Your Own Hidden Gems

The beauty of sailing the British Virgin Islands lies in the freedom to create your own path. Between the main islands, you’ll discover more than 17 anchorages, each with its own character and charm. Sandy Spit might become your personal paradise, a tiny gem where you can spend hours watching the golden path the sun paints on the water. Or perhaps Salt Island will capture your imagination with its fascinating history and underwater wonders, including the legendary R.M.S. Rhone wreck.

The British Virgin Islands Tourism Board describes the archipelago as “easy to get to, but still a hidden enclave of secluded serenity.” This perfectly captures the essence of exploring the BVI’s hidden gems—accessible adventures that still feel like discoveries. Your visit can be anything you wish it to be, whether that means hiking to panoramic vistas, snorkeling vibrant reefs, or simply finding that perfect beach where your footprints are the only ones in the sand.

In the end, the most meaningful hidden gems might be the moments and memories you create while sailing these spectacular waters. Never underestimate the power of the dolphin pod that dances in your wake, the perfect sunset at anchor or the friendships formed with fellow sailors along the way. The true treasure of the BVI is that no two journeys ever feel the same, ensuring that each visit reveals opportunities to those willing to seek them.

Discover the Caribbean as you’ve never seen it before.

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It began the way these things often do—not with a plan, but with an invitation. A friend had chartered a boat in the British Virgin Islands and asked Mike and Cyndi Crosby to come along. It was meant to be a vacation, just a relaxing getaway. But as soon as Mike stepped aboard, something clicked.

“The second we got down and got on the boat, my brain was already spinning,” he recalled. “As soon as we left the dock and started sailing, I looked at my wife and said, ‘All right, we’ve got to figure out how to do this on our own. I don’t want to have to wait to be invited back.’”

That spark ignited a journey that would unfold over the course of nearly two decades. From YouTube tutorials and beginner books to ASA navigation courses and charter captain checkouts, the Crosbys’ transition from wide-eyed guests to confident owners wasn’t sudden—it was a steady climb. What started with wonder became a calling. And eventually, it became a way of life.

From Student to Skipper: Earning the Helm

In the early days, Mike set out to educate himself however he could. He devoured the growing catalog of YouTube sailing channels like SV Delos, not just for the aspirational stories but to learn—watching closely how skippers trimmed sails, navigated anchorages, handled systems. He read Sailing for Dummies, and on subsequent charters with his friend, he eagerly took the helm at every opportunity.

But there was a limit to what he could learn aboard big boats. Most of the vessels they chartered were large catamarans—44 feet and up—built for stability, not feel. “The helm can be fairly dead on big cats,” Mike explained. “You really don’t know how the weather’s affecting it. You can’t tell if your sails are properly trimmed and the boat is balanced.”

That lesson came into focus when he bought a 28-foot monohull to sail on a local lake. It was the smallest boat he’d ever sailed—and by far the most instructive. “When I first got out there with full sail up, anytime a puff came across the lake, I’d get that weather helm and broach right into the wind,” he said. “I didn’t understand the dynamics—I thought I had a bad boat.”

But what he had, in fact, was a teacher. The lake and the boat taught him to listen. A sudden heel meant the sail plan was wrong. A broach was a message, not a malfunction. He learned to reef early, to trim with precision, to feel the subtle shifts in balance through the tiller. It was a kind of learning no catamaran could offer.

As the idea of captaining their own charter began to take shape, Mike faced his next hurdle. A trusted base manager in the BVI—a man they’d chartered with for years—told him he’d need more than a good recommendation. A high credit card limit helped, but so did an ASA 105 certification in Coastal Navigation. Mike took the course and found it helpful, especially in understanding tides, currents, and chart plotters. But in the end, he remained convinced: nothing beats time on the water. “If I had to have a choice between someone who’s never taken the courses but has sailed for five years, or someone who’s taken every class and never sailed—I know which boat I’m getting on.”

His moment of truth came soon after, during their first bareboat charter as captain and crew. The base manager motored out of the harbor with them, watching closely as Mike raised the main and put the boat through a few maneuvers. Then, without fanfare, he peeled off in his dinghy.

“He was like, ‘All right, looking good. Have a great trip,’” Mike recalled. “I looked at Cyndi and my parents, who were my crew, and I said, ‘Oh, we’re doing this. He left.’ Evidently, he liked what he saw. And now it was on us to bring the boat back.”

They did. And they kept coming back.

Falling for the BVI—And Returning Home

What began as a one-time invitation gradually turned into ritual. Over the years, the British Virgin Islands became more than just a favorite cruising ground for Mike and Cyndi Crosby—they became their second home. Not just for the postcard-perfect beauty or the predictability of the trade winds, but for something more enduring: connection.

“The cool thing about the BVI,” Mike said, “is it’s not just one island. Each one has its own personality, its own vibe. It’s like sailing through a chain of neighborhoods.” That mix of variety and familiarity is what keeps them coming back. Some anchorages offer peace and solitude—places to drop the hook and not see another boat for hours. Others are social hubs, alive with music, cold drinks, and warm conversation. “You can choose your own adventure,” he added. “That’s what makes it so special.”

But what truly anchors them is the people. After so many seasons afloat, the Crosbys have cultivated a network of friends on nearly every island—local restaurant owners, charter base staff, fellow cruisers.

“We call them family,” Cyndi said. “We check in with them every time we return. It’s not just a vacation anymore—it’s personal.”

Cyndi finds tranquility in the quiet corners of the BVI: the soft sands and still water of Pomato Point on Anegada, often empty except for their boat; or Benures Bay on Norman Island, where the sunsets glow over Saint John and the world feels far away. Mike gravitates toward the energy of North Sound, Virgin Gorda, where anchoring off Prickly Pear puts you within dinghy distance of Saba Rock, Bitter End, and Leverick Bay. On land, their favorite haunts include CocoMaya for dinner on the beach, and Hog Heaven, perched high above the hills, serving barbecue with arguably the best view in the Caribbean.

Even after so many visits, the BVI continues to feel new—alive with both memories and possibility. “It’s like having a vacation home,” Mike said, “but we get to move it from island to island.”

And for now, it’s a base that fits. With kids still in college and life back home tugging at their calendar, the BVI offers the perfect mix of accessibility, variety, and ease. “We’re still in a phase where we can’t go off grid for months at a time,” he admitted. “But in the meantime, this is where we want to be.”

For the Crosbys, it’s not just about where they sail—it’s about how it makes them feel. The islands may be small, but they contain a world of meaning.

Making the Leap to Ownership

The idea of owning a boat—of not just borrowing the lifestyle, but building it—remained in the background for years. Then, at the Annapolis Boat Show in 2021, Cyndi nudged the dream into motion. After walking through a few boats, she turned to Mike and asked, “What are you waiting on?”

That day, they signed a contract for a Fountaine Pajot Isla 40.

For Mike, the timing was never going to be perfect. “It’s like having kids—you’re never really ready. You just do it,” he said. But the decision wasn’t just about owning a boat—it was about building a platform for the life they wanted.

Rather than keep the Isla for private use, they placed it in the Waypoints charter fleet in the BVI, largely because of their long-standing relationship with Anthony, the base manager. Trust, Mike emphasized, was everything. “I just know it’s going to be taken care of better than I could take care of it from 2,000 miles away,” he said.

They knew going in that charter ownership wasn’t a passive investment. Revenue ebbs and flows with the seasons, and during hurricane haul-outs, the expenses don’t stop just because the bookings do. “You’ve got to plan for the downtime just like you plan for the income,” Mike said. “Some months are great, some not so much.”

What’s made the difference, they believe, is their mindset. Rather than relying solely on the management company, they’ve taken an active role—marketing the boat, helping guests book trips, even stepping into new professional territory. Cyndi, who’s long helped friends plan vacations, is now earning her travel agent certification to formalize the work she’s already been doing behind the scenes.

“We treat it like a business because, well, it is one,” Mike said. “I love boats. I love the maritime industry. I want to be around people who feel the same. And I think that energy shows.”

For owners looking for less involvement, he acknowledges that guaranteed income programs offer predictability—but often at the expense of flexibility and oversight. “Whatever path you take,” he advised, “just take some ownership. Know what you’re signing up for.”

Lessons Learned, Upgrades Earned

Now, after two and a half years with the Isla, they’re preparing to step into the next phase: a new Fountaine Pajot 44. The decision to upgrade didn’t come out of restlessness but from experience—two and a half years of living with their Isla 40, learning what worked, what didn’t, and what they wanted more of.

“We always figured if it all worked out, we’d eventually move into that mid-40s range,” Mike said. When Fountaine Pajot announced their new 44—featuring design upgrades trickling down from their larger models—it felt like the right boat at the right time.

The changes may seem incremental on paper, but for the Crosbys, they’re meaningful. The new 44 adds an island in the galley for more prep space, a better seating layout, and most notably, an upper flybridge lounge—a significant improvement over the twin sunpads on their current boat. Storage is smarter. Ventilation is better. And for Cyndi, who handles the anchoring duties, there’s a game-changer: a redesigned anchor locker that’s no longer buried under cushions on the foredeck. “Now I just pop open a table lid and it’s right there,” she said, laughing. “I won’t be half-inside the locker anymore trying to get the bridle on.”

Other upgrades speak to the lessons learned only after spending real time aboard. The forward cabins now feature full-size beds, not just tapered doubles that give guests the short end of the stick. There’s more room for water toys, more thoughtful airflow throughout, and just enough extra storage to avoid the constant shuffle of gear. “We realized over time how much those small details matter,” Mike said. “And this new boat just checks the boxes we didn’t even know we had until we started using the first one.”

Cruising on Their Terms

Looking back, Mike doesn’t believe they’d do much differently—though Cyndi jokes he might’ve dragged his feet a little early on. They nearly bought a used Voyage 440 just before the COVID-19 pandemic. The closing was scheduled for Friday, March 13, 2020—the same week the world seemed to tilt. As a restaurant owner facing the prospect of lockdowns, Mike backed out. “It just didn’t feel like the right time to take on a boat,” he said. That decision delayed their dream another three years.

But in hindsight, it may have been exactly the timing they needed. “Those were the years our kids were in high school and headed off to college,” he reflected. “We were in the thick of it—driving them around, being present. I don’t know that we could’ve really used the boat the way we intended back then.”

Now, as near-empty nesters, they have the flexibility to take two- or three-week trips without the stress of juggling school schedules or the sense of missing out. Their plan has never been to live aboard full-time—but to build a lifestyle that lets them step away and truly be away.

That’s what the new boat represents—not just more comfort and capability, but a deeper embrace of the life they’ve spent nearly twenty years building. From the spark of a charter trip to the helm of a purpose-built catamaran, every step has been intentional. And for the Crosbys, the journey is still just getting underway.

The post From Charter Dreamers to Catamaran Owners: A Life Built Under Sail appeared first on Cruising World.

St. Thomas, U.S. Virgin Islands — Tensions are rising between neighboring territories in the Virgin Islands as the Virgin Islands Professional Charter Association (VIPCA) urges the U.S. Virgin Islands government to implement reciprocal licensing measures in response to recent fee increases by the British Virgin Islands.

The controversy stems from a decision by BVI authorities to impose significantly higher licensing fees on U.S.-based vessels conducting charter business in BVI waters. The new measures, part of the Commercial Recreational Vessels Licensing (Amendment) Act, 2025, have sparked concern among U.S. Virgin Islands operators who argue that the increased costs are punitive and threaten the regional charter industry’s cooperative foundation.

In a public statement, VIPCA described the BVI’s move as “short-sighted and unfortunate,” claiming that the new regulations place an unfair burden on USVI-based charter vessels. In response, the organization is calling on the USVI government to take action by enforcing existing laws more rigorously and implementing reciprocal fees and compliance requirements for BVI-based vessels entering USVI waters.

Concerns Over Economic Impact

VIPCA points to the size and significance of the marine tourism industry in the USVI, which it says supports more than 5,000 jobs and contributes over $166 million annually to the local economy. The association warns that without intervention, businesses may be forced to relocate to the BVI, creating ripple effects across a wide network of supporting industries including marinas, mechanics, grocery stores, restaurants, and hospitality services.

“The USVI charter industry is at risk,” VIPCA said. “Every vessel that relocates to the BVI or day charter business that shuts down means not just the loss of that operation, but impacts across the entire maritime supply chain.”

The association has outlined several steps it believes the USVI government should take immediately, including:

• Imposing matching licensing fees and access restrictions on BVI-based charter vessels
  
• Requiring proof of U.S. customs clearance for all foreign vessels prior to passenger embarkation or disembarkation
  
• Enforcing compliance with U.S. Coast Guard crew credentialing and vessel safety requirements
  
• Mandating the use of the U.S. eNOA/D arrival and departure system

A Call for Cooperation—or Competition?

While the BVI government has not publicly responded to VIPCA’s latest statements, officials there have defended the fee increases as part of broader efforts to strengthen oversight and regulatory compliance within their waters. The BVI’s charter sector has also grown significantly in recent years, with local stakeholders pushing for policies that ensure more direct economic benefit to the territory.

Some in the region worry that a tit-for-tat regulatory approach may damage long-standing cross-border tourism ties. For decades, charter boats have freely cruised between the USVI and BVI, offering visitors seamless itineraries that span both territories.

VIPCA, while advocating for reciprocity, also emphasized its preference for a collaborative future. The organization has proposed the concept of a “Greater Virgin Islands Sailing Zone”—a joint initiative between the BVI and USVI to streamline regulations and foster shared maritime prosperity. But for now, VIPCA says, the BVI’s decision to act unilaterally has forced the USVI to respond in kind.

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“Fish On! Fish On! Fish On!”

Havana, my 8-year-old son, yelled as the reel on the aft rail began to sing. It was mid-morning on our seventh day out of Bermuda, sailing down to the British Virgin Islands. The Puerto Rico Trench and the open Atlantic were behind us; we were over Kingfish Banks with the islands of Tortola and Jost Van Dyke in sight ahead.

I reeled in a 20-pound wahoo as our two kids and the crew gathered around, providing encouragement. Dressing and filleting the fish was a bloody operation that the kids watched with gory delight. After the aft deck was washed down, I called Foxy’s Tamarind Bar on the VHF radio, asking if they would grill up the wahoo for our dinner that evening. There would be six of us, and there was no other option, since we’d run out of propane.

Jost Van Dyke is the best place to clear into the BVI. The customs and immigration office is in the building at the foot of the town dock. Foxy’s being willing to cook up our dinner was a bonus to anticipate as we sailed in that direction.

On our way there, we stopped to cool off at Sandy Cay. We dropped the hook, dove overboard and swam to the beach. It was a few days before Thanksgiving in 2009, with our cold New England lives three months behind us. Searcher, our 57-foot Bowman ketch, had carried the six of us safely through gales and calms, over the Gulf Stream and through the Bermuda Triangle to this paradise of blue sky, warm water and gentle winds. 

By the time we’d left Maine, both kids were already savvy boat rats. They’d grown up on and in the water, and on Searcher. They could swim by the time they were 2, row a boat by 4, and paddle their own kayaks and sail a dinghy by 6. The family had been in the BVI when they were young, but there’s little they remember. This time, they were 8 and 10 and ready for adventure.

We were spending the entire winter exploring the islands from the BVI down to Grenada and back. To get the boat here, we’d been joined on the delivery from Newport, Rhode Island, by a young couple, Rob and Emily. They’d be flying back north soon, but first, we spent a few days at Foxy’s, sailing around to West End on Tortola to take on fuel, water and propane, and then sailing over to Norman Island to prepare for Thanksgiving.

Norman Island still had the original Willy T back then, anchored in the Bight, surrounded by dozens of charter boats. I’ve always favored Kelly’s Cove behind Water Point, away from the crowd. You could drop the hook in sand and run a stern line ashore to keep the boat pointing north. There was room for only a few boats. I’d spent months anchored there when I was single.

As a family, we’d have nearly a month to spend in the Virgin islands before heading south—lots of time for the kids to explore the pirate caves, sandy beaches, coral reefs, markets, museums and old colonial ruins.

The pirate caves on Treasure Point were overcrowded with charters, so we took the dinghy to a walk-in pirate cave above the waterline. It’s on the point between Soldier and Benures bays. There’s just enough room to nose the dinghy in and offload young treasure hunters. The reefs were worth an hour of snorkeling, too.

After that, since we were dropping off the crew at St. John’s in the US Virgin Islands, we had to clear immigration at Cruz Bay. There’s no getting our 57-foot ketch into the inner harbor, so we picked up a park mooring outside and took everyone ashore in the dinghy. The family then had the afternoon to explore the village.

Cruz Bay is a bustling village with ferry boats coming and going, shops, stores, a post office, a hardware store and, at the top of the hill, a modest market with a larger supermarket a 10-minute walk away. We stocked up after visiting the National Park Service visitors center, next to the dinghy dock across from the immigration office. 

The next day, we motored over to Maho Bay, where, on one of my previous boats, I’d ridden out Hurricane Luis in 1995. Ashore was the Maho Bay eco-campground, since taken over by more upscale cottages, but the beach is great. I’m told there’s a knock-up village there with a food truck now.  

Around Mary Point to the east is Leinster Bay, and the Annaberg sugar and rum plantation. We anchored (you pick up moorings today) and went ashore to explore. There’s a well-maintained trail from the beach up to the grounds of this sprawling plantation—a step back into the colonial period. No one was there, but the signage explains the process of turning sugar cane into sugar and the by-product, molasses, which is then turned into rum.

We cleared back into the BVI at West End, Soper’s Hole, and spent the afternoon snorkeling around The Indians off Pelican Island.

The anchorage and beach on Deadman’s Bay, to the east of the Peter Island Resort, can be crowded, but there’s good snorkeling around Cabey Point. The next day, I took the kids to the wreck of the Rhone, off the western shore of nearby Salt Island. This British mailboat sank during a hurricane in 1867. The wreck became a classroom for underwater film and photography workshops I ran in the 1990s. The stern section, rudder and propeller are near the beach and can be explored with a mask and snorkel. The rest of the ship, scattered over the bottom, descends more than 60 feet. Dive operators on Tortola will meet you there with all the gear. 

We anchored off the old village on Salt Island and took the dinghy around to the Rhone so the kids could free dive down to the stern section. Later that afternoon, the kids paddled their kayaks to the beach to explore the abandoned settlement and salt works that once extracted salt from the salt ponds. The kayaks proved invaluable, as the kids could go off on their own (always together) to explore. They had a sense of freedom and independence, and we got a few hours of peace on the boat. We also brought their bikes aboard, but they were seldom used. Island roads are usually too narrow and full of potholes.

Bring off the grid with no TV or, in those days, social media, the kids lived life in the present. We had board games, books, and painting and drawing materials. Havana began building model boats from scraps of wood. (Today, she is a graduate yacht designer and naval architect.)

Searcher provided us with a backyard for play. I’d brought along hip harnesses so the kids could clip into a halyard and swing out over the water, from bow to stern and back again. We also had a boogie board and used it to tow the kids behind the dinghy. The 15-hp outboard had enough power to get them water skiing and wakeboarding.

Swimming with Dolphins

Julie had heard about a park on Tortola where the kids could swim with dolphins. It was based at Prospect Reef Resort in Road Town. We sailed over and anchored, then spent a few hours one afternoon watching Ren and  Havana become familiar with two of the dolphins. They hugged and stroked their new friends, and got dragged the length of the pool, thrown into the air. It was hard to tell who was having more fun, them or the dolphins.

That facility was wiped out in Hurricane Irma in 2017. Still, Road Town is a busy place, more so now than 15 years ago. Today, there’s a cruise ship dock, shopping malls, supermarkets and the huge Moorings charter operation. There was a time when this port was a small, quiet village with just two stores for provisioning.

What hasn’t changed is that the BVI is a great place to start a life of Caribbean cruising. The sailing is easy. You can pick up a mooring every afternoon in a different cove or off a beach where there’ll be a bar and a restaurant. It’s just more boats now, so start early each morning in order to pick up your next mooring by noon.

A 10-day, around-the-islands sail will help you feel more confident before undertaking more adventurous voyages farther down the island chain—such as the one we did next, heading from the southern tip of Virgin Gorda for the French island of Guadeloupe, 200 miles and 36 hours to the southeast.

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Celebrate the Holidays at Bitter End: A Season of Joy, Festivity, and Island Magic

As the holiday season approaches, Bitter End Yacht Club is gearing up to transform the sparkling waters of North Sound into a vibrant celebration of the season. From cherished traditions to exciting new experiences, there’s no better place to bask in the warmth of the Caribbean spirit. Whether you’re planning a family getaway, a romantic escape, or a festive gathering with friends, their holiday offerings promise something for everyone.

Christmas Cheer and Traditions

Kick off the season with our Christmas Eve Boat Parade. Decorated vessels will light up the night as they glide through the North Sound, a stunning spectacle you won’t want to miss. Santa will also make his traditional stop at Bitter End on Christmas Eve, arriving not by sleigh but by sea—an island twist on a beloved tradition.

A Holiday Feast to Remember

Our culinary team has crafted special holiday menus that celebrate the flavors of the Caribbean. Indulge in island-inspired takes on traditional holiday fare, served alongside seasonal cocktails that are as festive as they are delicious.

New Year’s Eve on the Water

Ring in 2025 with style at Bitter End’s New Year’s Eve Celebration. Start your evening with a delectable feast at the Quarterdeck, then head to the dance floor for a lively night of music and cocktails. As the clock strikes midnight, toast to the New Year under a sky filled with dazzling fireworks reflected on the sea.

Festive Experiences for All

The holidays at Bitter End aren’t just about the big events; they’re also about the little moments that make the season magical. From their renowned Rum Tastings at the Quarterdeck Bar to Watersports Excursions that immerse you in the beauty of the BVI,  each day holds new opportunities to create unforgettable memories.

For those seeking serenity amidst the festivity, indulge in a rejuvenating SUP yoga session, or simply relax on the beach with a good book from the Quarterdeck Library.

Give the Gift of Bitter End

Looking for the perfect gift? The new custom Aloha Bags and other exclusive Bitter End Provisions make ideal presents for the ocean lovers in your life.

Celebrate the Season with Bitter End Yacht Club

This holiday season, escape to Bitter End for a celebration filled with joy, adventure, and the unmatched beauty of the British Virgin Islands. Join them as they create memories that will last a lifetime, surrounded by the people and places that make this time of year so special. Book your stay today and let Bitter End Yacht Club be part of your holiday tradition. Whether it’s for one of our signature events or a week of relaxation and fun, they can’t wait to welcome you to their slice of paradise.

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As Bitter End Yacht Club continues to expand its offerings, the arrival of e-foiling—thanks to an exciting partnership with BVI E-Foil—marks a new era in the club’s storied history. This innovative sport, which allows riders to glide effortlessly above the water, is set to become a cornerstone of the Bitter End experience, providing both adventure and tranquility on the stunning waters of North Sound.

Marina and Watersports Manager, Nick Putnam says, “BVI E-foiling was the obvious choice for a partner on this endeavor because of their extensive knowledge of the sport. Combined with our excellent location, it was the ideal choice to build out our program.”

For the watersports program, E-Foiling has been a celebrated addition to the program. Putnam continues, “It’s rounded out the waterfront nicely. At Bitter End, we’ve traditionally been focused on wind sports, and sailing excellence has been a long standing part of our history, E-foiling has made getting on the water more accessible for those guests who might be hesitant to harness the power of the breeze, and provides for those who love wind sports, something to do when the rare BVI day leaves the winds whispering rather than roaring.”

Embarking on an e-foiling adventure at Bitter End is as seamless as it is exhilarating. Guests are invited to visit the watersports center, where a team of skilled instructors awaits to guide them through the experience. Much like surfing, the progression from laying on the board to kneeling and then standing is intuitive, and within two hours, most participants are confidently soaring above the water, feeling the rush of flight coupled with the serenity of gliding over North Sound’s pristine, protected waterways.

The unique geography of North Sound—its calm, flat waters sheltered by lush islands—makes it an ideal setting for e-foiling. Here, riders can fully immerse themselves in the experience, free from the concerns of choppy seas or too much boat traffic. The sensation of effortlessly floating above the water, with the breathtaking BVI landscape as a backdrop, offers a perspective unlike any other.

Lauren Hokin, a founding family member of Bitter End, captures the spirit of this expansion: “It is heartwarming and exciting to see our Club Fleet growing again with new ways to explore our watersports playground. Our Club Fleet is central to the Bitter End experience. We are thrilled to welcome new opportunities for adventure and education on North Sound as we chart a course towards an even brighter future.”

E-foiling at Bitter End is more than just a new activity; it is an invitation to explore the beauty of the British Virgin Islands in an entirely new way. As BEYC continues to grow our offerings and expand our Club Fleet, the crew is excited to see how e-foiling will inspire and delight guests. Whether you are seeking adventure, education, or simply a new way to connect with the water, e-foiling at Bitter End promises an experience that is both thrilling and unforgettable.

Beyond e-foiling, the watersports crew has more exciting additions to the Club Fleet this year. Bitter End has also invested in several RS Zest dinghies, perfect for both novice sailors and seasoned enthusiasts alike. These versatile dinghies offer a dynamic sailing experience for adventure sailing or racing around the buoys of the North Sound. 

Additionally, the introduction of adventure SUP excursions and SUP yoga brings new dimensions to stand-up paddleboarding, combining fitness, exploration, and the serene beauty of the surrounding islands. And for those who crave underwater adventure, Kinto’s popular snorkel excursion has returned, to the resounding delight of guests eager to explore the vibrant marine life of the BVI.

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Andrew Thompson answers his phone breathless, having just come ashore from the afternoon’s racing activity. “I’m on a busman’s holiday in the UK sailing my ‘Solo” – a 12-foot dinghy in a super-competitive fleet,” he explains. To say that the founder and director of Horizon Yacht Charters is passionate about sailing is an understatement. He lives and breathes life on the water.

Thirty years ago, a nine-month contract to run the watersports program for a five-star hotel on Virgin Gorda enticed the Englishman to the British Virgin Islands. In 1998 he co-founded Horizon Yacht Charters, and today Thompson is fully entrenched in the Caribbean life.

“Clearly I love it,” he laughs. “I certainly have a disposition for watersports and windsports. We kitesurf, we wingfoil; it’s just spectacular.”

Thompson is humble about his enviable sailing experience and accomplishments, which include myriad regatta-class wins, and more than 50,000 sea miles. Providing a charter experience that is far above and beyond the norm is his passion.

What began as a fledgling charter operation with three boats has expanded into a fleet of nearly 60 sailing yachts, including monohulls and catamarans, between 34 and 65 feet. Horizon Yacht Charters operates from two locations: the headquarters on Tortola in the BVI and another location on St. Vincent in the Grenadines. From learn-to-sail to bareboat and skippered to luxury crewed, Horizon offers the full complement of yacht charters—with the option of a private-jet charter in tandem. Thompson credits the company’s longevity to its relationship with its discerning yacht owners and charter clients.

A Stone’s Throw From the Dock

“Our clients know everyone in our reservations department,” Thompson says. “There’s Courtney, who has been with the company for 26 years; Christalen, who joined in 2006; and Sandra, who came on board in 2018. Kaleigh runs the crewed-yacht division, and everyone knows our operations director, Henry, who runs the dock.

“Our staff are right there,” Thompson continues. “Our guests aren’t dealing with a remote office or with someone who has never been to the location or on the boats they’re looking to book. When you book a boat with us at our Caribbean locations, you’re booking a specific boat, not just that model. Our reservation team have been on every boat and often walk clients through the yachts virtually to show the immaculate condition, the layout and specific equipment. They are a stone’s throw from the dock and are very integrated into the whole business.”

Perfectionism at Its Finest

The majority of the owners of the boats in Horizon’s fleet are sailors, and with that comes an expectation that the boat will be maintained to the highest standards.

“We have a long-standing relationship with the yards that build the boats for our fleet, and we have a commitment to the owners to maintain the boats in pristine condition. We can keep boats in our fleet up to eight years because we keep up with the maintenance. I’m a bit of a perfectionist in that area.

“We keep the canvas, sails, cosmetics, mechanicals and electrics in top condition,” he continues. “Each bareboat charter application is carefully reviewed to ensure that the charterer has the appropriate amount of knowledge and experience for the particular vessel. On the docks, there is not a stack pack open, the main sails are put away. That is the attention to detail and the day-to-day of how we operate. These standards are the bedrock to the experience.”

As the company grew, Thompson knew he didn’t want to spend his life on a plane trying to manage fleets all over the world to his exacting standards. So he developed a points system and a worldwide sailing program that allows an owner use of his own boat in the BVI/Caribbean and aboard other boats in partner fleets worldwide.

The Horizon Yacht Charters Difference

Charter guests who want to sail farther afield than the BVI/Caribbean don’t have to venture out on their own; Horizon Yacht Charters offers the same personalized service through a brokerage arrangement with preferred fleet operators in the USVI, Bahamas and Croatia and beyond.

Yacht management and sales are integral to the charter operation, and through the Horizon Yacht Sales division, Thompson and his experienced team consult with owners on every aspect of a yacht purchase, covering the nuances of  builders, or boat models, factory options and bespoke customizations. The company is the authorized dealer for Nautitech Catamarans and Bavaria Yachts in the English speaking Caribbean and distributor for CNB brands including Lagoon, Beneteau, Jeanneau, and Excess, in addition to Fountaine Pajot among others.

Horizon is an American Sailing Association sailing school for its learn-to-sail charters and do offer some boats with asymmetric spinnakers. “We’ve had Quantum Sails design asymetric sails specifically for charter use,” he says. “It electrifies your performance downwind. We are the only charter company to offer these boats.

“We live and breathe the sport of sailing, and we do it to a very high standard. That’s what I’m most proud of,” Thompson continues. “We are a very knowledgeable team passionate about putting out immaculate boats and giving people a great experience. If they want to learn more, we have a sailing school. We can also arrange for excursions such as diving, mountain biking, kitesurfing, hiking and snorkeling. We aren’t just another charter company.”

For more information, please visit: horizonyachtcharters.com

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