Meet the Captains and Crew
At Hennessy Sportfishing, we believe that your fishing charter experience is only as good as the people and boats behind it. That’s why we take pride in offering a top-tier fleet of fully equipped vessels and a team of experienced, passionate captains who know the waters of Marathon, Florida like the back of their hand.
Whether you're heading offshore for mahi-mahi, tuna, sailfish, or dropping lines on the reef for snapper and grouper, our boats and crew are ready to deliver a safe, fun, and productive day on the water.
Captain Kerry Hennessy – Florida Keys Fishing Guide & Owner of Hennessy Sportfishing
Captain Kerry is a third-generation Floridian, born on a shrimp farm in Arcadia, FL. He was raised on a tropical fish farm just south of Tampa, where his love for fishing took root early. As a kid, Kerry spent every spare moment fishing the waters of Tampa Bay—riding his bike to spillways, piers, cuts, and runouts to chase snook, sea trout, and redfish with his buddies.
In 1992, Kerry’s parents purchased a home in Marathon, Florida. His father Tim—an avid and successful angler—also bought a classic 30’ Rybovich pocket sportfishing boat. Together, they spent countless days fishing for mahi and tuna in the Florida Keys before Kerry left for college.
His passion for fishing shaped much of his life and travels. After college, Kerry spent five years living and fishing in the Bay Islands of Honduras, especially around Roatán—an incredible destination where landing a blue marlin and a bonefish in the same day wasn’t out of the question. His fishing adventures have taken him all over the world, including Mexico, Belize, Costa Rica, Panama, the Dominican Republic, Puerto Rico, Alaska, and the Bahamas.
Eventually, the call of the Keys brought him back. Today, Captain Kerry shares his love for the ocean and fishing with visiting families, anglers, and adventurers alike. He finds the greatest joy in helping create unforgettable experiences—especially when he hears a kid say, “Dad, this is the best day of my life.” That’s what it’s all about.
At Hennessy Sportfishing, our goal is to help make lasting memories and bring families and friends closer together on the crystal-clear waters of the beautiful Florida Keys.
Captain Dez – World-Class Fishing Guide
With a lifetime spent chasing game fish around the globe, Captain Dez brings unmatched experience, passion, and professionalism to every charter. From the cold, rugged waters of Alaska to the giant bluefin tuna of Massachusetts, and down to the vibrant coasts of Mexico, the reefs of the Fiji Islands, and the Florida Keys — Captain Dez has fished it all.
Renowned for creating unforgettable fishing adventures, Captain Dez has earned a reputation for excellence, consistently receiving 5-star reviews from anglers of all experience levels. Whether it’s your first time holding a rod or you’re a seasoned sportfisher, you’ll be in expert hands.
With a deep respect for the ocean and an instinct for finding the best fishing spots, Captain Dez combines local knowledge, top-tier gear, and a personalized approach to ensure every trip is safe, successful, and memorable.
And the adventure doesn’t have to end when the fishing does. By night, Captain Dez transforms into a lively karaoke host — a perfect way to cap off the day after enjoying your fresh catch. Ask him where he’ll be hosting next and join in for a few laughs, some great tunes, and maybe even a duet or two.
Book your next fishing trip with Captain Dez and discover why guests return year after year.
Meet Captain Randy
With over 20 years of fishing experience in the Florida Keys, Captain Randy brings deep local knowledge, patience, and a passion for sharing the thrill of fishing with others—especially families. Whether you're chasing offshore game fish or just looking to enjoy a laid-back day on the water, Captain Randy knows where to go and how to put you on the bite. A true local expert, he’s dialed in to the seasonal patterns, reef and wreck hot spots, and hidden gems that make the Keys one of the best fishing destinations in the world. Captain Randy is the perfect guide for both first-time anglers and seasoned fishermen looking for a fun, safe, and memorable day on the water.
Meet Ian – Full time Mate and Captain in Training
With years of fishing experience in the Florida Keys, Ian brings local knowledge, patience, and a passion for putting guests on the fish. Whether you're chasing offshore game fish, working the reefs and wrecks, or simply enjoying a day on the water, Ian knows how to help make it a great trip.
Ian is also the guy you want around when something needs fixing. With extensive hands-on knowledge of boats and marine systems, there isn't much on a boat he can't troubleshoot, repair, or figure out. His mechanical skills and experience on the water make him an invaluable part of the Hennessy Sportfishing team.
Currently, Ian is working alongside our captains as a mate while completing the requirements for his Captain's License. This gives him even more hands-on experience with our boats, our guests, and fishing the waters around Marathon.
We can't wait for the day Captain Ian officially takes the helm! Until then, you may find him working the deck, helping put guests on fish, keeping our boats running, and learning everything he can along the way.
Meet Captain Eric – Our Lobster Guy!
Captain Eric has called Marathon home since 2014 and has spent those years building an incredible knowledge of the waters and marine life of the Florida Keys.
Before becoming a charter captain, Eric worked collecting and transporting marine life for aquariums around the world. That unique background gave him extensive hands-on experience with Florida Keys marine life and an understanding of the local waters that he now enjoys sharing with our guests.
Captain Eric is also Hennessy Sportfishing’s go-to lobster guy. From daytime lobster trips to nighttime bully netting, Eric knows where to look, what to look for, and how to teach guests the techniques that make lobstering in the Keys such a unique experience.
Around Marathon, Eric is also known as the guy to call when you need bait delivered. He supplies bait locally to fishermen and captains, which means he stays closely connected to what’s happening on the water and what the local fishing community needs.
Whether you’re fishing, lobstering, learning about local marine life, or simply exploring the waters around Marathon, Captain Eric brings knowledge, patience, and a genuine love for the Florida Keys to every trip.
If lobster is on your Florida Keys bucket list—or you just want to spend the day with someone who truly knows these waters—Captain Eric is a great guy to have on the boat.
Meet Marie – The behind-the-scenes force keeping much of Hennessy Sportfishing’s digital world running
Marie is the behind-the-scenes force keeping much of Hennessy Sportfishing’s digital world running. From managing the website and online scheduling to handling booking details, photos, videos, and social media content, if it involves a computer or a camera, there’s a good chance Marie is behind it.
With a background in photography and website design, Marie combines her love of the outdoors with her creative side. You’ll often find her with a camera in hand, a drone in the air, or a GoPro or 360 camera somewhere on the boat—capturing everything from fishing trips and tournaments to boat races, sandbar days, and life around the Florida Keys.
When she’s not behind the camera, she’s usually behind a laptop managing Hennessy’s Squarespace website, updating trips and availability, coordinating scheduling, creating marketing content, and helping make sure guests have the information they need before getting on the water.
Splitting her time between Tampa and Marathon, Marie may not always be the person you see on the boat, but she’s often the person behind the website, booking process, photos, videos, and messages that helped get you there in the first place.
Want professional content from your day on the water? Marie is also available for charter photography and content creation, including photos, drone footage, GoPro and 360° video. Whether you want your fishing trip captured or need professional content for your own business or charter operation, learn more about our Florida Keys Offshore Photography & Content Creation services.