A Charter to Remember: Captain Glenn Shephard’s BVI Voyage with The Moorings

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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