Islamorada Offshore Fishing Charters

Come aboard the Pretty Work with Captain Jordan Wolk for an unforgettable day of offshore fishing or swordfishing in Islamorada

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Let's Fish

Islamorada Offshore Fishing Charters

Come aboard the Pretty Work with Captain Jordan Wolk for an unforgettable day of offshore fishing or swordfishing in Islamorada.

View Our Trips
Let's Fish
Discover the Best of Islamorada Fishing

Our Offshore Experiences

Our Islamorada fishing charters offers two distinct and unforgettable offshore experiences: general offshore charters and swordfishing trips. On a standard offshore trip, anglers explore wrecks, patch reefs, and natural bottom areas just a few miles from shore, or head further offshore during the summer to chase mahi mahi and tuna. These trips are fast-paced, family-friendly, and focused on a variety of species, combining trolling, kite fishing, and live bait techniques.

Swordfishing trips, on the other hand, are a true trophy hunt, venturing 25–30 miles offshore into the deep waters of the Gulf Stream. These trips require patience and precision, as anglers rig their own baits on hand-crank or electric reels, set two rods, and focus on that one epic bite from a massive swordfish. Together, these options provide something for every angler, from action-packed days of multiple catches to the thrill of targeting a single, world-class predator.

From $1,200 | 4-8 Hours

Islamorada Offshore Fishing

Offshore fishing charters offer an unforgettable experience that captures the best of Islamorada’s world-famous fishing.
$2,800 | 8+ Hours

Islamorada Swordfishing Charter

A typical swordfishing trip out of Islamorada is a full-day adventure that begins with a 25–30 mile run offshore to the deep-water grounds where swordfish are most active.
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Experience & Passion

Capt. Jordan Wolk

Born and raised in South Florida, Captain Jordan Wolk has spent his life on the water, chasing everything from snook to billfish. In 2008, he made the move to the Florida Keys, where he began working out of the legendary Bud N’ Mary’s Marina. After five years mating on various boats, he launched his freelance captain career, quickly earning a reputation for his expertise, work ethic, and easygoing personality. From 2016 to 2025, he captained a top-performing tournament team, culminating in a 2025 Quest for the Crest Sailfish Series Championship. This is one of the most prestigious achievements in competitive sportfishing.

Whether you’re a first-time angler looking to hook your very first fish or a seasoned tournament fisherman aiming to refine your tactics, Jordan  is known for his patience, professionalism, and dedication to making every trip memorable. His goal is simple - create an unforgettable experience tailored to your interests, skill level, and sense of adventure on the water.

10+ Years of experience
Licenses Included
Family Friendly
Available All-Year
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Meet the Pretty Work

46’ Whiticar

The “Pretty Work” is a classic 46′ Whiticar built in 1974, beautifully maintained and known for her exceptional seaworthiness. Repowered with twin 490 Cummins engines, she cruises comfortably at 26 knots, making offshore runs smooth and reliable. The boat features air conditioning, a modern indoor bathroom, and a recently updated salon for comfort between fishing action. The bridge is fully equipped with advanced electronics, and with an experienced and knowledgeable captain at the helm, every trip aboard the Prety Work is both safe and memorable.

UP TO 6 PASSENGERS
SAFETY EQUIPMENT
Bait & Gear provided
Fish cleaning included
Our BOAT
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Trophies of the Florida Keys

Species We Target

We offer experiences that range from fast-action offshore fishing to deep-water trophy hunts.

Spanish Mackerel

Spanish mackerel are fast, schooling fish that provide lots of action, especially for light tackle anglers. They are abundant near reefs and natural bottom areas and are perfect for a quick, exciting catch.

Snapper

Snapper are a staple of our nearshore bottom fishing, providing consistent action. Popular species include mutton, lane, and yellowtail snapper, which are perfect for dinner straight off the boat.

Mahi Mahi

Mahi mahi are colorful, fast, and aggressive, making them one of the most exciting species to target offshore. They are often found near floating debris or weed lines and are typically caught on light tackle with live or artificial baits.

Wahoo

Wahoo are known for their incredible speed and sharp teeth, offering an adrenaline-packed fight. They are usually caught while trolling in winter months and are prized for their firm, delicious meat.

Sailfish

Sailfish are prized for their speed, acrobatics, and spectacular fights on the line. We target them kite fishing or trolling live baits, making for a thrilling sight-fishing experience.

King Mackerel

King mackerel are aggressive predators often found near schools of baitfish. They are typically caught trolling or using live bait, and their hard runs make them exciting for sportfishing enthusiasts.

Amberjack

Known as “reef donkeys” for their strength and stamina, amberjack are powerful fighters found around deep wrecks and ledges. They provide thrilling battles for anglers using heavy tackle year-round.

Blackfin Tuna

Blackfin tuna are smaller, fast, and energetic, providing fun action for both beginners and experienced anglers. They are commonly found near offshore humps and patch reefs and can be caught trolling or with live bait.

Cobia

Cobia are strong, surface-oriented fish that are often sight-cast along structure or near floating debris. Known for their fight and taste, they can be caught on live bait, jigs, or even drifting lures.
Where our Trip Begins

Our Location

(754) 281-4993
wolkjordan@yahoo.com
Bud N’ Mary’s Marina 79851 Overseas Hwy, Islamorada, FL 33036