Join Miss Penny Charters LLC for an 8-hour fishing expedition in Islamorada, where you'll chase sailfish, tuna, and reef species for a full day of adrenaline and angling success. Perfect for all skill levels, this trip combines offshore action with reef fishing near the Florida Keys' renowned waters.
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Difficulty
moderate
Duration
8 hours
Fitness Level
Participants should be in reasonable physical shape to handle a full day on the water and possibly some boat movement.
Wildlife
History
Islamorada has a long-standing history as a hub for sportfishing dating back to the early 20th century, shaping its reputation worldwide.
Conservation
Miss Penny Charters emphasizes responsible fishing and sustainable practices to preserve the rich marine environment for future generations.
Miss Penny Charters LLC
Join Miss Penny Charters LLC for an 8-hour fishing expedition in Islamorada, where you'll chase sailfish, tuna, and reef species for a full day of adrenaline and angling success. Perfect for all skill levels, this trip combines offshore action with reef fishing near the Florida Keys' renowned waters.
Miss Penny Charters LLC is a professional fishing charter company based in Islamorada, Florida, specializing in full-day, half-day, three-quarter-day, split, and swordfish charters. The captain and crew operate licensed, safety-focused charters that target offshore and reef species along the Florida Keys, offering experienced guidance for anglers of all skill levels.
Trips include live-bait starts, reef and wreck fishing, and deepwater swordfishing excursions that explore depths between 1,400 and 1,800 feet. Miss Penny Charters provides all necessary fishing equipment, local knowledge of seasonal species, and flexible itineraries that adjust to weather and fishing conditions to maximize success and safety. The company emphasizes clear booking policies, transparent pricing for private and split charters, and professional maintenance of onboard gear and safety equipment.
For anglers seeking variety, options range from four-hour half-day trips to ten-hour swordfish hunts and eight-hour full-day charters that combine pelagic and bottom fishing. Split charters are available for groups up to four anglers when the trip fills, making offshore experiences more accessible. Miss Penny Charters is locally rooted in Islamorada and follows applicable Florida fishing regulations and conservation practices. Customer confidence is supported by on-water experience, targeted fishing itineraries, and a commitment to safe, responsive service. Whether pursuing snapper, grouper, amberjack, wahoo, tuna, sailfish, or swordfish, clients can expect focused instruction, species-specific techniques, and a professionally run charter designed for memorable, catch-oriented outings. Reservations are available year-round subject to seasonal availability, and the crew provides pre-trip information on gear, regulations, and suggested preparations for anglers of every experience level.
Location
Islamorada, FL
Heart of the Florida Keys
Trip Durations
4–10 hours
Half, ¾, full, swordfish options
Deep Fishing
1,400–1,800 ft
Swordfish depths targeted
Split Charters
Up to 4
Shared trips book when filled
Book private or split trips — half, ¾, full day, or 10-hour swordfish expeditions. Limited spots, reserve early.
Arrive early
Getting on the water at sunrise increases your chances of a productive day.
Bring sun protection
Sunscreen, hats, and polarized sunglasses help shield you from the strong Florida sun.
Pack light but wisely
Bring just essentials—water, snacks, and a camera—since space on the boat is limited.
Be adaptable
Conditions can change; trust your guide to adjust tactics for optimal fishing.
Sunscreen
Protects your skin during long hours under the sun.
summer
Polarized sunglasses
Reduces glare and improves visibility into the water.
Hat with brim
Maintains shade and keeps the sun out of your eyes.
summer
Light, breathable clothing
Keeps you cool and comfortable throughout the day.
summer