Meet the Fleet and Captains
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 – Your Family-Friendly Florida Keys Fishing Guide
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.
The Fleet
Mako 28
Captain Kerry, Dez, and Randy
Center Console
6 Person Capacity
Boat Manufacturer: Mako
Engine Model: Yamaha
Powered by: 2 x 200 HP
Boat Length: 28ft
Year Built: 1992
Year Restored: 2023
Equipped With: GPS, Fishfinder, Flybridge, Live Baitwell, Outriggers, Icebox for bait, Icebox for fish, Icebox for food and drink, Wireless Trolling Motor, Radar, and Spearfishing Equipment
Charters: Inshore fishing, nearshore fishing, wreck fishing, reef fishing, deep sea fishing, bridge fishing, sunset cruises, sandbar trips, reef snorkeling, wreck dives and sandbar trips.
Pick up location: 108 Ave A, Marathon, FL 33050
Venture 34
Captain Randy
**Bathroom**
Center Console
6 Person Capacity
Boat Manufacturer: Venture
Engine Model: Yamaha
Powered by: 2 x 200 HP
Boat Length: 34ft
Year Built: 2005
Year Restored: 2020
Equipped With: GPS, Fishfinder, Flybridge, Live Baitwell, Outriggers, Icebox for bait, Icebox for fish, Icebox for food and drink, Wireless Trolling Motor, Radar, and Spearfishing Equipment
Charters: Inshore fishing, nearshore fishing, wreck fishing, reef fishing, deep sea fishing, bridge fishing, sunset cruises, sandbar trips, reef snorkeling, wreck dives and sandbar trips.
Pick up location: Captain Hook’s Marina Dive Center, 11833 Overseas Hwy, Marathon, FL 33050
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