From Charter Dreamers to Catamaran Owners: A Life Built Under Sail

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.

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