Florida Key Fishing Trips
At Hennessy Sportfishing, we offer unforgettable guided fishing trips from Marathon, Florida—the heart of the Florida Keys. Our private charters are perfect for anglers of all levels, with trips ranging from 3 to 10 hours. Whether you're after offshore trophies like mahi-mahi and tuna, or prefer reef and wreck fishing for snapper and grouper, Captain Kerry Hennessy and crew will tailor your trip for the best results.
We provide all gear, bait, and local expertise—just bring your sunscreen, water, and a sense of adventure. No fishing license required.
3 Hour Inshore Fishing Charter
Short on time but still want to get out on the water? Our 3-hour trip is the perfect quick escape to experience fishing in the Florida Keys.
This trip is designed as an introduction to fishing—great for beginners, kids, and families looking to learn the basics, catch a few fish, and enjoy time on the water. While you’ll definitely have the chance to hook into some action, this trip isn’t focused on filling the cooler or bringing home dinner—it’s all about fun, learning, and making memories.
You can also mix it up with some snorkeling or a quick sandbar stop, making it a well-rounded adventure for everyone on board.
This trip is limited to five guest on the Boca. Please book the Mako, Venture or Hatteras for parties 6
4 Hour Reef and Wreck Fishing Charter
One of our most popular trips, this 4-hour charter is perfect for anglers looking to catch fresh fish and enjoy steady action on the water. Depending on wind and sea conditions, we’ll fish either the Atlantic reef line or the calm waters of Florida Bay to provide the most comfortable and productive experience possible.
These trips are ideal for families, beginners, and experienced anglers alike. We typically focus on filling the cooler with great-eating fish while targeting a variety of Florida Keys favorites including Yellowtail Snapper, Mangrove Snapper, Grouper, Mackerel, Barracuda, and other hard-fighting reef species. Seasonal opportunities may also include Cobia, Wahoo, or Kingfish.
We run up to 10 miles offshore on the Oceanside and up to 12 miles into the Bayside waters during this trip. Every charter can be customized to match your group’s preferences and fishing goals, whether you want fast action, dinner for the table, or a mix of both.
This trip is limited to five guest on the Boca. Please book the Mako, Venture or Hatteras for parties 6
3 or 4 Hour Sunset Fishing Charter
Short on time but still want the full Florida Keys experience? Our 3 and 4 hour sunset fishing trips are built for action. We target reef and nearshore species that bite hard and fill coolers — then cruise home as the sky turns orange over the Gulf. This isn’t a slow sightseeing tour. This is bent rods, tight lines, and golden-hour memories.
Perfect for families, couples, and anyone who wants to fish without committing to a full day offshore.
This trip is limited to five guest on the Boca. Please book the Mako, Venture or Hatteras for parties 6
6 Hour Reef, Wreck, Bridge or Gulf Trip
Captain Favorite! Experience a dynamic day on the water with our Reef and Wreck Fishing trip—venturing on the ocean side when the bite is hot and weather conditions allow. We'll target a wide variety of prized species, including Mutton Snapper, Yellowtail, Amberjack, Kingfish, Cero Mackerel, Sailfish, Tuna, Cubera Snapper, Black Grouper, Wahoo, and Mahi Mahi. If ocean conditions are rough, no worries—your adventure continues in the sheltered waters near the 7-Mile Bridge or in the Gulf targeting additional species.
This trip gives you enough time to change it up if something isn’t working due to conditions or if you have already caught a limit of targeted species, you can go target something else. I’m a fan of the 6 hour trip.
This trip is limited to five guest on the Boca. Please book the Mako, Venture or Hatteras for parties 6
6 Hour Offshore Trip
Join us for an unforgettable offshore adventure targeting Tuna and Mahi Mahi, with exciting opportunities to reel in Wahoo and Sailfish when in season. These trips are perfect for anglers seeking action-packed days on the water and the thrill of big game fishing.This is an offshore trip. This can include deep dropping in the summer and a run to the famous Marathon humps for blackfin tuna and mahi mahi.
Year-round action targeting snapper, grouper, tarpon, barracuda, sharks, and seasonal offshore species like mahi, tuna, sailfish, and swordfish depending on conditions.
This trip is limited to five guest on the Boca and Mako. Please book the Venture or Hatteras for parties 6
*An additional fuel surcharge applies on the Venture 34 for offshore trips
8 Hour Offshore Trip
Join us for an unforgettable offshore adventure targeting Tuna and Mahi Mahi, with exciting opportunities to reel in Wahoo and Sailfish when in season. These trips are perfect for anglers seeking action-packed days on the water and the thrill of big game fishing.This is an offshore trip. This can include deep dropping in the summer and a run to the famous Marathon humps for blackfin tuna and mahi mahi.
Year-round action targeting snapper, grouper, tarpon, barracuda, sharks, and seasonal offshore species like mahi, tuna, sailfish, and swordfish depending on conditions.
This trip is limited to five guest on the Boca and Mako. Please book the Venture or Hatteras for parties 6
*An additional fuel surcharge applies on the Venture 34 for offshore trips
10 Hour Offshore Trip
Built for hardcore anglers, this full-day offshore adventure gives you the time and range to fish some of the Florida Keys’ most productive waters. We’ll target the famous Marathon humps for Blackfin Tuna and Mahi Mahi, run & gun offshore weed lines, deep drop with electric reels during the summer months, or head to deep wrecks and gulf towers depending on conditions and the bite.
This trip offers exciting opportunities to target Tuna, Mahi Mahi, Wahoo, Sailfish, Snapper, Grouper, Tarpon, Barracuda, Sharks, and even Swordfish when conditions are right. With 10 hours on the water, we have the flexibility to fish multiple areas and techniques to maximize the action.
Whether you’re chasing fast-paced offshore bites, deep water species, or trophy fish in the Florida Keys, this charter delivers an unforgettable big game fishing experience for anglers of all skill levels.
This trip is limited to five guest on the Boca and Mako. Please book the Venture or Hatteras for parties 6
*An additional fuel surcharge applies on the Venture 34 for offshore trips
Add On - Snorkel and Sandbar Trip - $100 per hour
Snorkeling and sandbar trips available as stand alone packages by the hour or as an add on to your existing fishing charter.
*Snorkel gear not provided, but you can rent gear from several local shops
Add On - Harbor Cruise - $100 per hour
Harbor or sunset cruise available as stand alone packages by the hour or as an add on to your existing fishing charter.