- August 27, 2026
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Dylan Hubbard got a call from one of his boats at about 3:30 on the afternoon of July 4.
The captain of the Florida Fisherman, which was on a 39-hour trip, had heard a distress call from a stranded boater nearby that needed towing. Coast Guard regulations, Hubbard says, don’t allow boats with passengers aboard to tow other vessels or even pick up the people stuck on the boat.
It’s a safety issue.
But there is “a law of the sea,” Hubbard says, that states if you're offshore and encounter someone in trouble you have to help them. “There's a certain responsibility.”
The captain who called Hubbard wanted to know what to do.
Hubbard, 35, is the fourth-generation owner and operator of Hubbard’s Marina, a sprawling business based at Madeira Beach’s John’s Pass Village and Boardwalk. The company is best known for operating fishing charters and trips that depart from the inlet connecting Boca Ciega Bay and the Gulf.
But fishing is just one of its businesses. The 110-employee company also owns nine vessels and operates party boats and private fishing charters as well as dolphin cruises, shelling trips, sunset cruises, a pirate ship and a ghost tour. There is also a seafood market, a boutique and operation of two Tampa Bay Ferry vessels for the Pinellas Suncoast Transit Authority. And in the past couple weeks, it's added a breakfast club cruise that offers a dolphin tour with bloody marys, mimosas and breakfast foods. (Company officials decline to share revenue figures.)
Hubbard was enjoying the holiday, meanwhile, when the call came in but immediately called the Coast Guard command and got permission for the Florida Fisherman to pick up the stranded boaters. By the time it reached them, though, the other boat was running and no longer needed help.
The Florida Fisherman and its crew returned to its trip.
It turned out the incident was just the beginning of the story, and as Hubbard well knows, a business owner doesn’t ever really get a day off. Even on a holiday.
And his workday was just starting.
If you have a set image of what a boat captain looks like, chances are Dylan Hubbard won’t match it. He more closely resembles action hero Jack Reacher from the book and television series than the Skipper on Gilligan’s Island or even Jack Sparrow.
He is a solidly built six feet, seven inches tall and 250 pound (with 10.5% body fat), and is a serious businessman who has much to do with his time.
Hubbard’s Marina traces its history back nearly 100 years and has been located at the Pinellas County tourist attraction, with its crowded boardwalk, gift shops and restaurants and bars for 50 of those years.
Dylan followed his father Mark, who is still involved but takes a “100,000-foot view” of the business, dividing his time between Gulfport and a family farm, and the business.
Walking along the boardwalk, the Hubbard name seems to be everywhere.
“There is no longer a tour boat along the boardwalk that isn't controlled or operated by Hubbard's Marina,” Hubbard says, adding that the company continues to add new attractions and sees demand remaining strong despite broader concerns about tourism.
And if that weren’t enough, Hubbard says it has also developed a boat-building operation and a media company.
Dylan first went to work for the family business when he was about 8-years-old.
He wanted to buy a boat and Mark told him he needed a job to do that. So, he started selling bait at the marina and over the years gradually worked his way through the business, cleaning shrimp tanks, taking out the trash and, later, working on the charter boats through middle and high school at Keswick Christian School in St. Petersburg.
He went on to study business and hospitalist management at the University of Central Florida, graduating in 2013.
He eventually earned his captain's license and initially expected his career to remain on the water for years before having to slow down “later in life” and transitioning into office.
But a back injury forced him from that path when he was about 21. The upside was, he discovered an aptitude for business management and marketing.
In 2015, Hubbard became the company’s vice president and one of his first projects was modernization, updating the technology, replacing Windows DOS-based systems with iPads.
Mark, 62, says the business was running well and had always been on the cutting edge. In fact, he remembers being approached by a local chamber of commerce to teach members how to build websites.
When Dylan joined, he was tasked in part with developing a social media presence for the company and web marketing. He eventually took on more duties, learning how to operate a business as he went.
“It’s worked out really well,” Mark says.
“He’s increased our market share to the Southeast, to the traveling fishermen. It's been a very good experience for all of us. And he has increased the growth dramatically, and he's a good manager, and we have a good flow, a good business plan.”
Hubbard’s grandfather Wilson Hubbard started in the business in the 1920s and moved it to John’s Pass in 1976. Wilson was 63 at the time. Mark 13.
Wilson Hubbard, according to the company’s history, was born in Memphis and came to Florida with his parents while traveling with a carnival.
The family settled down in the nearby beach town of Pass-a-Grille, then a small town and today a neighborhood on St. Pete Beach. At the time, the story goes, the community had 162 residents, one policeman and a bootlegger.
Wilson made a living catching and selling fish from The Merry Pier on Eighth Avenue.
The company’s history says Wilson was 17 when he paid a concessionaire $150 for five rowboats and 40 cane poles.
He bought his first charter boat after serving in World War II and in 1954 established the first Gulf Coast half-day fishing party boat. Wilson’s father ran the business in his absence. In 1956, Wilson started an 18-hour fishing trip and in 1971 established overnight weekend trips.
Eventually, in 1978, The Friendly Fisherman Restaurant was added.
According to Dylan Hubbard, his father Mark and Mark’s brothers and sisters eventually took over the family business. (Mark bought Hubbard’s Marina in 2005 from his mother and sister but continued to work in the family business.)
The business, Hubbard Enterprises, owned some property on John’s Pass where they built a six-story parking garage and a three-story piece of the boardwalk.
The work started in 2007 and wasn’t completed until 2011. It was difficult time, Dylan Hubbard says. There was the economic crisis in 2008, some “bad hurricane years” and the Deep Water Horizon oil spill in the Gulf in 2010.
“We had all these momentous acts of God during a $27 million construction project,” he says.
“So, long story short, they lost the property in bankruptcy” and around 2010 Bank of America took over as property owners.
Dylan and Mark’s business — Hubbard’s Marina — was separate from the family and leases its space now. The family still owns The Friendly Fisherman. Mark is involved in that, but Dylan isn’t.
Dylan's sister, Tara Hubbard, is also involved in the company. She works in business development and is responsible for managing and expanding public private partnerships. Dylan says Tara is the reason Hubbard's Marina won the Tampa Bay Ferry contract.
Dylan Hubbard credits much of the company’s success today on being “blessed to grow up in an entrepreneurial family.” And while he still gets out on the water to fish on occasion, he’s found that staying on shore and working in the office is where he’s most effective in making the company profitable and focusing on growth.
But there have been challenges.
The pandemic, of course, put a damper on tourism as have outbreaks of red tide. But the biggest trouble came in 2024 when the area faced back-to-back hurricanes.
The first was Hurricane Helene which hit in late September and brought roughly nine feet of water along with sand and debris onto the John’s Pass boardwalk. The main dock at the property was also lost.
“We were totally buried, destroyed, flooded,” Hubbard says.
There was a fear among some in the community John’s Pass would be closed for as long as a year, but 24 dump trucks were brought in to get the sand out of the parking lots and the team at Hubbard’s was working around the clock to make repairs and get back open.
It reopened five days after Helene.
Then there was Hurricane Milton.
“This storm continued to head at us, and it was kind of numbing,” says Hubbard. “We were like, ‘I can't believe this is happening again.’”
Milton didn’t cause as much serious damage as Helene because, as Hubbard says, everything was already destroyed. But because of the heavy winds it did knock out power, the internet and infrastructure across Pinellas County.
Hubbard’s closed again, this time for about 10 days.
But Hubbard, ever the entrepreneur, saw in the disasters, crass as this may sound, an opportunity.
The company documented the clean up after Helene, posting videos on its YouTube channel and on social media that garnered thousands of views — one was watched by more than 600,000 people. Hubbard also became a face on national TV, appearing on news programs multiple times a day “for weeks.”
“It was a lot of good press,” he says. The goal was not solely self-promotion but getting “the word out that ‘hey, we're open again.’”
Open for business is a constant part of Hubbard's routine. Going back to that July 4, he got another call, around 6 p.m. This one was from the Coast Guard.
The Florida Fisherman had gone back to fishing after first approaching the stranded boat.
Now, hours later, the Coast Guard was trying to reach that boat, again: it had broken down a second time and again needed help.
The Florida Fisherman headed back out and picked up the four passengers. But the boat stayed behind secured by an anchor.
Hubbard says the crew of the Florida Fisherman got to the dock with both sets of passengers — its own and those of the stranded boat — the following morning, Sunday, at 6 a.m.
About three hours later, it was heading back to pick up the boat and tow it back.
While this rescue may sound adventurous to those not familiar with the nautical world, it’s just part of the job for Hubbard. Just like creating profit and loss statements, managing employees, dealing with customers is.
Which is the point of the anecdote.
It’s pretty common to hear from the Coast Guard when you're offshore, he says. What the Coast Guard will do is put out a notice to mariners and if you're within a certain distance you’re expected to lend a hand if you can.
“In this case, we were so close, we were we were the ones that got called into to help,” he says.
So they did.
It’s all in a day’s work, after all.
