A Story of Vision, Grit, and a Love Affair with the Sea
The Idea at Sea
The sun was slipping into the Mediterranean, that hour when everything turns to gold — water, sky, even the bottle of red passed around the cockpit table. A few friends were on a charter sail, the kind of trip where conversation meanders as lazily as the wind. Between laughter and the slap of halyards against the mast, someone said it out loud: “Wouldn’t it be amazing if you could have a boat like this… without actually owning it?”
That single sentence, tossed into the air like a paper airplane, would eventually reshape modern boating.
When George Bonelli, a project manager from New Jersey with a knack for systems and a restless curiosity, returned home to Austin, Texas, he couldn’t shake the idea. “You spend a week living aboard this beautiful, well-kept yacht,” he recalled, “then you go home to your friend’s beat-up old boat and think — there has to be a better way.”
By 2001, that spark had a name: SailTime. The goal wasn’t to build another charter business. It was to reimagine ownership; to give people the experience of owning a yacht, minus the burden that usually came with it. It was radical, almost heretical, in a boating world still anchored in tradition.
Bonelli started small: one boat on a lake in central Texas, four members willing to try something unproven, and a real-time online scheduling system that felt futuristic at the time. The first memberships sold out in weeks. Then came the second boat and the same story repeated.
And then came doubt. The first sailboat arrived just weeks after 9/11. The country was reeling, luxury purchases seemed out of touch, and the idea of shared access felt foreign. “We honestly didn’t know if anyone would sign up,” Bonelli said. “But they did. They kept coming.”
That was the moment SailTime stopped being an idea and became a movement — a quiet rebellion against the limits of ownership, and a new way to chase freedom on the water.
Today, as SailTime celebrates its 25th anniversary, that same spirit — a mix of curiosity, courage, and good wine — still flows through its fleet. From one boat on a Texas lake to 30 club bases worldwide, the company has grown into one of the most trusted names in fractional sailing. But for everyone who’s ever taken the helm, it’s still about that same feeling: the horizon ahead, the hum of the wind, and the freedom to just sail.
From Lake Austin to the World
By 2002, SailTime had begun to catch a steady breeze. Word spread through yacht clubs and sailing schools; whispers of a Texas startup where you could reserve a yacht online, show up with your crew, and sail away without a single slip fee or maintenance bill. To lifelong boat owners, it sounded like sorcery. To a new generation of sailors, it sounded like freedom.
The concept was simple, but the execution required precision: high-quality boats, consistent maintenance, real-time scheduling, and trust. Bonelli built systems to manage it all, turning what could’ve been chaos into a smooth experience. “We weren’t selling boats,” he’d later say. “We were selling time, connection, and confidence.”
Over the next four years, SailTime grew from one lake in Austin to dozens of marinas across the globe. Each new base was more than a business, it was a community, a floating neighborhood of sailors who shared stories, wine, and weather reports. It was a sailing club fleet powered by both technology and human connection.
Growing Pains and the Turning Tide
With rapid growth came growing pains. By 2006, SailTime had expanded faster than its small Austin team could steer. It was time to evolve — from scrappy startup to structured, seaworthy enterprise.
That year, a group of successful base owners, including Todd Hess, Wayne Diviney, and Bob Remsing — joined forces to acquire the SailTime brand and assets. The operation moved to Annapolis, Maryland, the beating heart of American sailing.
“It was the right time for a new tack,” Bonelli said. “We had proven the model worked. Now we needed experienced sailors and business leaders to carry it forward.”
The transition was seamless and smart. SailTime became a franchise organization, giving local entrepreneurs the ability to run their own bases with corporate support, technology, and branding. It was a model that mirrored its own philosophy — shared ownership, shared success.
The Crew Behind the Compass
Every great voyage begins with a dreamer — and for SailTime, that was founder George Bonelli, whose original vision still guides the fleet like a compass rose on every chart.
When Todd Hess stepped aboard, he brought new wind to the sails. A lifelong sailor who grew up on the Jersey coast, Hess saw not just what SailTime was, but what it could become. “Freedom has always been our North Star,” he said. “But real freedom takes structure. You have to build the systems that make adventure possible.” Under his leadership, SailTime expanded its fleet, refined its technology, and grew into a global network that still feels local at every marina.
As CEO, Hess is flanked by two longtime shipmates: Wayne Diviney, the steady hand at the financial helm, and Bob Remsing, the builder and connector who keeps relationships strong from dockyard to boardroom. Diviney, a CPA turned sailor, likes to say, “You can measure success in numbers but at SailTime, we measure it in sunsets shared.” His calm precision gives the company ballast, ensuring that passion and pragmatism move in tandem.
Remsing, meanwhile, embodies SailTime’s entrepreneurial grit. “Every idea has to float — literally and financially,” he laughed. From his Chicago sailing club base, he’s helped shape partnerships with manufacturers and introduced innovations that ripple across the fleet. His perspective is grounded in practicality, but his motivation remains emotional: the joy of seeing new sailors fall in love with the water.
Then there’s Kristen Diviney McGarr, the digital heartbeat of the operation. Her work behind the scenes ensures that SailTime’s scheduling, member tools, and franchise systems run as smoothly as a fair-weather tack. “Technology is our invisible crew,” she said. “When it works right, it feels effortless, just like a perfect sail.” McGarr represents SailTime’s next chapter: data-driven, experience-focused, and human at its core.
Together, they form the modern helm — a crew as comfortable with spreadsheets and servers as they are with sails and sea spray. They don’t just run a company; they steer a community, keeping Bonelli’s original promise alive: to make the freedom of sailing something everyone can share.
A Quarter Century of Wind and Wonder
Twenty-five years later, SailTime stands as a pioneer in shared boating — a model that predated the “sharing economy” by nearly a decade. Its success lies not just in innovation, but in community. Every sailing club base is a reflection of local waters and local people, bound together by a shared love of the sea.
SailTime’s approach has inspired spinoffs, imitators, and entire industries built on similar principles. Yet its soul remains the same as it was in that Mediterranean cockpit — accessible, adventurous, and a little rebellious.
“Our members aren’t customers,” Hess said. “They’re sailors. They’re part of something bigger; a community that values freedom, learning, and connection.”
Across its 25 global bases, from the Chesapeake to Sydney, SailTime continues to open doors — or rather, hatches, for people who might never have thought a yacht was within reach. It has given thousands their first taste of sailing, their first night at anchor, their first sunrise over quiet water.
Looking Ahead: The Next Horizon
If the last 25 years were about redefining ownership, the next 25 will be about expanding access even further. SailTime’s expansion to PowerTime, its growing network of sailing schools, and its embrace of new technologies are all part of that future.
“We’re always evolving,” McGarr said. “Whether it’s app-based scheduling, smarter fleet management, or better training tools, everything we do is about making boating simpler, smarter, and more enjoyable.”
The global conversation around sustainability has also found a home at SailTime. More members are drawn to sailing for its low environmental footprint and its connection to nature. “There’s nothing greener than moving by wind,” Diviney added.
Hess envisions the next era as one where access and adventure are indistinguishable. “Freedom awaits — that’s our message,” he said. “The freedom to learn, to explore, to share. The water doesn’t care what you own. It only cares that you show up.”
Epilogue – The Toast
It’s evening again, somewhere warm, somewhere with boats rocking gently against their lines. A few SailTime members sit in the cockpit, watching another sun sink into another sea. The wine is different, the faces new, but the feeling; that quiet, unshakable joy of being on the water — is exactly the same as it was twenty-five years ago.
Here’s to the dreamers who started it, the sailors who carry it forward, and the waters still waiting ahead.
