Islamorada, Florida Keys
Deep Sea Fishing Islamorada
The Gulf Stream runs just 15 miles offshore. Trophy Mahi, Tuna, Wahoo, Sailfish, and Swordfish are waiting — aboard the 43ft Miss Penny Tiara Yacht.
What Is Deep Sea Fishing in Islamorada?
Deep sea fishing — also called offshore fishing — means heading beyond the reef into open ocean water, typically 100 feet deep and beyond. In Islamorada, that means venturing out to the Gulf Stream, where warm blue water pushes bait and big pelagic fish within reach of anglers willing to make the run.
What makes Islamorada exceptional is proximity. The Gulf Stream's edge sits just 15 miles southeast of the reef — one of the closest access points in the entire United States. You're in the blue water fast, spending more time fishing and less time running.
On a Miss Penny deep sea charter, we run fast aboard our 43ft Tiara Yacht with twin turbo Cummins QSM11 diesels. We cover ground efficiently, find the right conditions, and put you on fish.
The Gulf Stream Advantage
The Gulf Stream acts like a conveyor belt for the ocean's top predators. Its warm, nutrient-rich water compresses bait schools and draws in the species you came to catch. When the stream pushes close — which it does regularly off Islamorada — the fishing can be spectacular.
Target Species
🐟 Mahi-Mahi (Dolphinfish)
The most sought-after offshore species in the Keys. Brilliant colors, aerial acrobatics, and incredible table fare. Best from April through August when they follow the current edge. Schooling fish — find one, find many.
Best Season: April–August | Depth: 100–600ft
🐡 Yellowfin & Blackfin Tuna
Blackfin tuna are year-round powerhouses found on current seams and reef edges. Yellowfin require venturing to the Gulf Stream blue water — but when you find them, the action is relentless. Both hit trolling lures and live bait.
Best Season: Year-round (Blackfin), Spring–Summer (Yellowfin)
⚡ Wahoo
The fastest fish in the ocean at 60mph+. Wahoo stack on the reef edge and offshore wrecks, especially October through March. High-speed trolling with lipped plugs is the go-to method. Outstanding table fare — known in Hawaii as "ono" meaning delicious.
Best Season: October–March | Depth: 100–200ft
🌊 Sailfish
Islamorada is world-class for sailfish, especially winter through early spring. Kite fishing with live bait is the technique — presenting baits in the surface film where sailfish can't resist. Miss Penny has hauled in multiple sails in a single day.
Best Season: November–April | Method: Kite Fishing
⚔️ Swordfish
The ultimate deep water challenge. Daytime swordfishing at 1,500–1,800ft using electric reels and weighted rigs. Available year-round from Islamorada. Requires a dedicated swordfish charter — an overnight or day trip focused solely on broadbill.
👑 Kingfish (King Mackerel)
Ambush predators that stack on the 80–120ft reef edge and current seams. Slow-trolling live bait or running a kite spread will get strikes. Year-round with peaks in spring and fall. Great smoked.
Best Season: Spring & Fall | Depth: 80–120ft
Deep Sea Charter Options
Full Day Charter
8 Hours | Up to 6 Anglers
Maximum time in the blue water. Run to the Gulf Stream edge, target multiple species, the full offshore experience.
View Details3/4 Day Charter
6 Hours | Up to 6 Anglers
The sweet spot. Enough time to reach offshore grounds, find fish, and come back with a cooler full.
View DetailsSwordfish Charter
10 Hours | Up to 4 Anglers
Dedicated deep drop swordfishing at 1,500–1,800ft. The ultimate deep sea challenge.
View DetailsWhy Miss Penny for Deep Sea Fishing?
Air-conditioned cabin, twin turbo Cummins diesels, and a ride that won't beat you up on the way out.
Bait, tackle, ice, water, fishing licenses — all covered. Just show up ready to fish.
Departing from Islamorada's world-famous marina — 77522 Overseas Hwy, Slip 8.
A crew that knows where the fish are and how to put you on them, every trip.
Book Your Deep Sea Fishing Charter
Check availability and book online instantly. Questions? Call us at (305) 290-1404