Fishing Charter Directory
Find trusted fishing charters in your area. All businesses are verified members of SAFE Fishing.
Chelsea Charters Islamorada
Our charter fishing boat the PHOEBE is a classic, meticulously maintained 48' Willis Craft with air conditioned salon and large cockpit with fighting chair to comfortably accommodate your group of anglers.
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Coral Sea Charters
Guests fish aboard a 38-foot Harris sportfishing boat, a classic 1978 vessel upgraded for modern comfort and performance.
DIRTYBOAT CHARTERS
DirtyBoat 2.0: Premier Offshore Sportfishing Operating out of the world-famous Robbie’s Marina in Islamorada, the DirtyBoat 2.0 offers the ultimate vantage point for the best bite in the Florida Keys. Because Islamorada is where the Gulf Stream comes closest to shore, this charter bypasses the long runs required from other keys and puts you on the fish faster. Whether you are a family looking for an unforgettable day on the water or serious anglers hunting a trophy, the DirtyBoat crew engineers moments you will talk about for a lifetime. The Vessel: 42' Liberty Express The DirtyBoat 2.0 is a 42-foot Liberty Express built for heavy seas, elite comfort, and championship performance. Power & Speed: Powered by 900 HP Twin Turbo Cummins Diesel Engines to outrun the fleet and maximize your fishing time. Premium Comfort: Features a plush, fully air-conditioned salon to escape the tropical heat, plenty of shade, and a private, clean restroom (head). Tournament Rigged: Equipped with a massive cockpit designed specifically for landing giant pelagics. The Arsenal & Target Species Captain Kit and his crew don't just fish; they compete in elite tournaments like the Gold Cup and Cheeca Presidential. That same championship-level strategy and gear go into every charter. Elite Gear: Outfitted with tournament-grade Shimano Talica and Tiagra reels, custom Rainshadow rods, and Lindgren-Pitman electric reels for deep-dropping. Advanced Tech: Armed with Garmin Livescope, side-scan sonar, and satellite temperature charts to actively hunt fish rather than wait for them. Target Species: Specializing in acrobatic Sailfish on the kites, fast-action Mahi-Mahi at "The Humps," deep-dropping for monster Swordfish (at 1,800 feet!), and filling the cooler with Snapper, Grouper, and Blackfin Tuna. The Captain & Crew Led by Captain Kit Mobley (Kit Carson), the DirtyBoat team combines pinpoint technical precision with a world-class hosting intuition. The crew prides themselves on a "No BS" approach: they provide the top-tier gear, the licenses, the bait, and the fish cleaning. You just show up ready to fish.
Drop Back Charters
The Drop Back is a 40-foot custom sport fishing boat with a 12-foot beam, designed specifically for reef, wreck, and offshore fishing in the Florida Keys.
Legasea Charters
LegaSea Charters is a family-run offshore fishing charter based in Islamorada, Florida Keys. Led by Capt. Joey Spaulding, a third-generation fishing captain, trips depart aboard the LegaSea — a 45' Carolina Custom that has been in the family since 1966. legaseacharters They offer half-day and full-day offshore trips (ranging from $1,200–$2,400) targeting species like swordfish, sailfish, mahi mahi, tuna, snapper, and grouper. The boat features an air-conditioned cabin, restroom, and plenty of room for families and groups. They're located at 84001 Overseas Hwy, Islamorada, and can be reached at (305) 731-6875.
Miss Penny Charters
Veteran-owned and operated, Miss Penny Sportfishing runs elite offshore charters out of Robbie's Marina in Islamorada aboard a tournament-rigged 43' Tiara 4300 Express. Powered by twin turbo Cummins QSM11 diesels, the Miss Penny is fast, clean, and air-conditioned with a full cabin and head. Captain Chad Pruitt brings nearly a decade of experience in Islamorada waters, targeting Sailfish, Mahi, Swordfish, Snapper, Grouper, and more. We offer full day, 3/4 day, swordfish, and split charter options — everything included: tackle, bait, ice, licenses, and fish cleaning. As DirtyBoat's sister ship and a fellow S.A.F.E. supporter, we believe in fishing hard and conserving harder. Named in honor of a mother whose legacy made the dream possible, every trip on the Miss Penny is personal.
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