Less than two years ago, Tony Ebeyer had never sailed a cruising catamaran. Today, he has logged more than 14,000 nautical miles aboard his Leopard 50 Dracarys, sailed throughout the U.S. East Coast, Bahamas, and Mexico, completed long offshore passages, and transformed his boat into a comfortable floating home and office. His story isn’t just about learning to sail. It’s about embracing a completely new chapter of life.
After raising three children, building and selling a successful company, and finding himself with the flexibility to work remotely, Tony began asking a simple question: What comes next? The answer turned out to be a Leopard 50.
Looking for the Next Chapter
As his children reached adulthood and began building lives of their own, Tony started thinking about what he wanted the next phase of life to look like. A business consultant who helps entrepreneurs grow and eventually exit their companies, he had already experienced several professional chapters. This time, he wanted something different.
“I started noticing the nest was becoming less occupied.”
Remote work gave him flexibility. His children no longer depended on living at home full-time. The opportunity to create a more mobile lifestyle suddenly became realistic. What began as casual curiosity quickly evolved into serious exploration.
From Complete Beginner to Leopard Owner
Unlike many cruisers who spend years sailing before purchasing a boat, Tony’s path accelerated quickly. It started with a sailing YouTube channel. After discovering cruising content online, he enrolled in a week-long sailing school in Florida and earned the certifications needed to charter a boat. Immediately afterward, he booked a bareboat charter aboard a Leopard 40 in the British Virgin Islands.
“After seven days of sailing school, they handed me the keys and said, ‘Have fun.'”
The experience left a lasting impression. A short time later, he returned to the BVI aboard a Leopard 50 with friends. That trip changed everything.
“It was the first time I stepped aboard a Leopard 50 and thought, ‘This could actually be my retirement.'”
Soon after, Tony attended a boat show, spent hours comparing models, and ultimately placed an order for a Leopard 50.
“I ordered the boat and then panicked.”
It’s a feeling many future owners can probably relate to. The decision wasn’t simply about purchasing a boat. It was about changing his lifestyle, becoming comfortable on a vessel far larger than anything he had owned before, and embracing the uncertainty that comes with trying something completely new.
Why He Chose the Leopard 50
Like many future owners, Tony spent countless hours comparing brands before making a decision. What ultimately convinced him was the combination of design, durability, and functionality.
One thing stood out as he toured boats at multiple shows. Even after several busy days filled with visitors, the Leopard models still felt solid and well-built.
“Three days into a boat show, you could already see wear and tear on some boats.”
Leopard’s charter heritage made an impression. The boats felt practical, serviceable, and designed to stand up to long-term use.
Another major factor was the helm position. Even before taking delivery, Tony believed the layout would suit the way he planned to cruise. Nearly two years later, it remains one of his favorite features. The upper helm provides excellent visibility while remaining connected to the salon, cockpit, and side decks, making it easy to move around the boat when underway.
The forward cockpit and signature Leopard forward door were equally important. Rather than walking around the side decks every time he wanted to move forward, Tony can simply step through the watertight forward access door.
“I thought I’d use it all the time and it turns out I do.”
Combined with the forward cockpit seating area, the space creates an entirely separate outdoor living zone. It’s a favorite spot for morning coffee, evening drinks, and entertaining guests.
While Tony cruises aboard a Leopard 50, many of the design features he values most continue in today’s Leopard 52, including the forward cockpit, comfortable helm position, and spacious liveaboard layout.
The First 14,000 Miles
Tony’s first major voyage began immediately after delivery. Taking ownership during hurricane season, he headed north to Annapolis under the guidance of professional training captains.
After several weeks of hands-on experience, he began cruising on his own.
What followed was an impressive first couple of years aboard:
- Delivery from Florida to Annapolis
- Return south through the East Coast
- Key West
- Sarasota
- St. Petersburg
- Offshore passage to Mexico
- Multiple Chesapeake Bay seasons
- Extensive cruising throughout the Bahamas and Exumas
One of his favorite stories came when he received a wedding invitation in Mexico.
“I was online booking flights and thought, wait a minute, why don’t I just sail there?”
That decision became his first major offshore passage without a training captain aboard and helped build the confidence that only real-world experience can provide.
Learning on the Fly
Despite his relatively short sailing résumé when he purchased the boat, Tony dedicated significant time to education.
One of the most valuable resources he found was Cruisers University at the Annapolis Boat Show. Over multiple years, he attended courses covering weather forecasting, electrical systems, diesel maintenance, anchoring, sail trim, offshore cruising, and countless other topics.
“Even when you don’t know what you don’t know, it helps point you in the right direction.”
Tony also completed coursework and earned a U.S. Coast Guard captain’s license. While it didn’t have as much impact on insurance as expected, the training provided valuable knowledge about navigation, regulations, and safety procedures.
Perhaps the most valuable lesson was spending time aboard with experienced training captains.
“Get time with a training captain as early as possible.”
For new sailors, few things accelerate the learning process more effectively than working alongside someone who has already done what you’re hoping to do.
Building the Right Leopard 50
One of the most interesting aspects of Tony’s story is the amount of thought that went into configuring the boat. Rather than blindly selecting factory options, he relied heavily on conversations with experienced Leopard owners.
“The greatest resource I had was talking with other owners.”
Many of the decisions he made continue to pay off today.
Among the factory options he would absolutely choose again are the engine upgrade, electric winches, generator, air conditioning, upgraded electronics package, additional displays, and bow sprit preparation.
After delivery, he added lithium batteries, solar panels, a watermaker, feathering propellers, Starlink internet, and several custom lifestyle upgrades designed around the way he uses the boat.
One upgrade stands above the rest.
“The feathering props were expensive, but I’d absolutely do it again.”
The reduction in drag, noise, and overall sailing performance improvement made the investment worthwhile.
Turning a Leopard 50 Into a Floating Condo
Because Tony lives and works aboard, many of his modifications focused on comfort and functionality rather than pure sailing performance.
The navigation desk became a true remote office complete with a monitor, comfortable chair, and dedicated workspace for consulting clients. Elsewhere aboard, he added a motorized television in the owner’s suite, expanded refrigeration capacity, smart-home technology, Starlink connectivity, and custom storage solutions.
“This isn’t just a sailboat. It’s my home.”
One of the smartest decisions was maximizing refrigeration. Instead of choosing a built-in dishwasher, Tony used the space for additional cold storage, a choice he’s never regretted.
“Refrigeration is critical. Dishwashing is minor.”
The result is a Leopard 50 tailored not only for cruising but also for everyday life.
Power, Comfort, and Realistic Expectations
Tony admits he entered cruising with unrealistic expectations about solar power. Like many new owners, he assumed a large solar array would dramatically reduce generator use.
Reality proved a little different.
His Leopard supports air conditioning, induction cooktops, computers, entertainment systems, refrigeration, water heating, and other comforts that consume significant amounts of power. Maintaining that lifestyle requires thoughtful energy management.
“The key is understanding how you actually use the boat.”
Instead of trying to eliminate generator usage entirely, Tony learned how to maximize efficiency. Generator time often becomes water-heating time, cooking time, battery-charging time, and air-conditioning time all at once.
The lesson was simple: build a power system around your actual lifestyle, not the one you imagine you’ll have.
Making the Most of Storage
One reason Tony chose the Leopard 50 was storage capacity. After nearly two years aboard, he believes it was one of the best decisions he made.
The Leopard’s charter-rooted design creates access throughout the boat, making it easy to separate mechanical systems from everyday living space. Battery relocations created additional pantry storage. Forward lockers became organized supply areas. Under-berth storage accommodates larger items that aren’t needed daily.
Tony even created an inventory system using bins and spreadsheets to track equipment and supplies.
“Everything has a place.”
For long-term cruising and liveaboard life, organization has become just as important as sailing skills.
Advice for Future Cruisers
When asked what advice he would give someone considering this lifestyle, Tony doesn’t hesitate.
“Do it.”
He understands the hesitation because he felt it himself. New boats are intimidating. Major life changes can be overwhelming. The learning curve is real. But after 14,000 nautical miles and nearly two years aboard, he has no regrets.
“You’re never going to know until you’ve done it.”
His advice is straightforward: take sailing lessons, charter before you buy, spend time with experienced captains, talk with current owners, and keep learning. Most importantly, don’t let uncertainty stop you from exploring something that genuinely excites you.
“You’ll regret the things you didn’t do more than the things you did.”
For Tony, what started as curiosity evolved into an entirely new way of life. And 14,000 nautical miles later, he’s still discovering new destinations, new skills, and new reasons to keep going.
Tony’s Leopard 50 may no longer be in production, but many of the features he highlights can be found aboard today’s Leopard 52, including expansive living areas, the forward cockpit, innovative helm design, and long-range cruising capability.
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