For Dylan Hubbard, fishing is the easy part.
The harder part is carrying nearly 100 years of family history on his shoulders while figuring out how to keep the operation alive through hurricanes, federal regulators and a rapidly changing Florida tourism industry.
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Hubbard is the fourth generation of his family to run Hubbard's Marina in Madeira Beach, Fla. The business traces its roots to 1928, when his grandfather started with five rowboats and 40 cane poles.
Today, Hubbard is vice president of the company and has begun the process of purchasing it from his father. But stepping into the family business was never as simple as inheriting a title.
"Oh, you have no idea," Hubbard told OutKick Outdoors when asked whether he had to earn his place before calling himself captain.
His grandfather, Wilson, originally ran the operation before leaving to serve during World War II. Hubbard's great-grandfather stepped in during that time, which is why the family considers it a fourth-generation business. His father later purchased the company from the family in 2004. Now, Dylan is preparing to carry it forward.
"It's also really cool to have that layer of: it's a family business. I'm fourth generation," Hubbard said. "Not only am I working, but also it's that legacy. So it's just an added layer of maybe responsibility or honor or blessing — whatever you want to call it — that really makes it even that much more special."
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That responsibility means knowing when to hold onto tradition and when to embrace change.
Hubbard's Marina began in Pass-a-Grille, back when Florida's barrier islands looked very different. But as new bridges changed traffic patterns and Pass-a-Grille became increasingly residential, Hubbard's grandfather recognized that the business needed a new home. Even though he was nearing 70 years old, he uprooted the operation and moved it north to John's Pass.
"He saw the writing on the wall," Hubbard said.
It was the kind of decision that probably felt risky at the time but proved essential in the decades that followed. John's Pass eventually developed into a major tourism destination, and Hubbard's grandfather also worked with the city to establish the boardwalk that now runs through the area.
That willingness to adapt has remained necessary — especially when nature delivered its worst, twice in less than two weeks.
In September 2024, Hurricane Helene brought nine feet of water into Hubbard's Marina. The main office was completely submerged, the main dock was destroyed, and the business lost infrastructure, inventory and equipment. Before the water had even fully receded, Hurricane Milton was bearing down as a Category 5, forcing the family to brace for a second direct hit while still standing in the wreckage of the first.
"It was pretty numbing," Hubbard said, "just a wild situation to go through."
Still, the boats survived. More importantly, so did the people.
Before official rescue crews could even reach the barrier islands, Hubbard and several crew members set out before daylight to assess the damage at John's Pass. What began as a trip to inspect the business quickly became something else entirely.
"We were the first boat out there," Hubbard said. "No one was out there — no fire, no EMS, no emergency folks. It was just us."
As they navigated through the damaged area, residents stood along seawalls crying, waving and begging for help. Some had stayed behind during the storm, become trapped, and then emerged to find they had lost everything.
"So what was supposed to be a search and find out what we needed to do and what got damaged turned into a rescue mission," Hubbard said.
Other members of the fishing community soon joined in, deploying their own boats to move people and supplies to and from the barrier islands — even as police tried, unsuccessfully, to keep boaters off the water given the debris and damage.
"We were essentially pirates for a week," he said.
For Hubbard, reopening quickly was never primarily about preserving the business's reputation or getting tourists back on boats. It was about his employees. At the time, the company had 84 staff members. Fifteen had lost everything in the storm.
"If I had just sat there and waited and not got to work, those people would not only have lost their homes and their vehicles and everything they owned, they would have also lost their jobs and not had income," Hubbard said. "So to me, it was imperative to open up as quickly as humanly possible."
The team rebuilt the dock in two days and had trips running again five days after Helene — faster than the barrier islands themselves officially reopened. The community later raised nearly $75,000 to help affected staff members.
In the year that followed, Hubbard's kept growing rather than pulling back: the company acquired a pirate ship, a dolphin tour boat and a shark tour operation in November 2025, adding to a portfolio that already includes a seafood market, a fuel dock and a boat-building operation. A new ghost tour just launched, and a Tampa Bay ferry service is next.
Capt. Hubbard may prefer being offshore, but much of his job now happens behind a desk, in meetings, or fighting battles that never make it onto a dock report.
Hubbard is heavily involved in fisheries management, serving as president of the Florida Guides Association and sitting on Gulf Council advisory panels covering reef fish, data collection and outreach.
A few years ago, that involvement got personal. After Hubbard publicly criticized weak enforcement against illegal charter operations at a federal meeting, NOAA's Office of Law Enforcement took a closer look at his own business — and told him the way Hubbard's Marina operated was against federal regulation.
It took him roughly 85 days to get the regulation itself changed, preserving his business model in the process.
"If you're not in the room, you're on the menu," Hubbard said of why he keeps showing up to meetings most people would find, in his words, "mind-numbing and boring."
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It's not the only wild thing nearly 100 years on the Gulf has produced. Ask Hubbard for his strangest moment on the water and the answer comes without hesitation: "We've found dead bodies. We've come across boats on fire. We've saved people." His grandfather ran across great white sharks; his father, orcas; Hubbard himself has crossed paths with pilot whales, a right whale and one of the largest leatherback turtles he's ever seen.
"People always ask me, 'Do you still get to go fishing?'" Hubbard said. "I do, and I make time for it, and I definitely get out on the water as much as I can."
But he also understands that spending all his time fishing wouldn't necessarily serve the larger operation.
"If I spent my time offshore, that's definitely where I would rather be and enjoy a lot more," he said. "But I definitely wouldn't be in the position we are today if I did that all the time."
Hubbard hopes his grandfather would approve of where the family business stands today.
"I hope he would be happy," Hubbard said.
The pirate ship, the ferry, the federal meetings — none of that existed when Wilson Hubbard started with five rowboats. But the motto he built the business on hasn't changed.
"If you're too busy to go fishing, you're just too darn busy."
Still true, four generations later.
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