Chasing Sailfish Through the Islamorada Shallows

In the Florida Keys, winter sailfish chase showering ballyhoo through the Islamorada shallows—and we chase the sails.
Sailfish cruising the reef
As winter settles in over the Florida Keys, a rather unprecedented opportunity arises as migrating sailfish begin their journey south along the edge of the Gulf Stream. Out along the reef line, where deep-blue water butts up against emerald shallows, sails can often be seen tailing as they ride the waves southward, hunting ballyhoo over the shallow sand just off the coast. AH360/Wirestock Creators/stock.adobe.com
Fishing boat running above the reef
This spectacle offers boats of every size a chance to get in on the action with short runs to find large numbers of billfish. It’s a helluva sight to behold. Jon Whittle
Capt. Sam Milazzo of Vice Versa Fishing Charters
“Ballyhoos and sailfish don’t get along very well,” says Capt. Sam Milazzo of Vice Versa Fishing Charters. “Those deep-water fish tend to come across the reef into the shallow water, and ballyhoo are their main source of food here in the Keys. It’s unique because you have shallow water really close to deeper water. The ballyhoos are just minding their business until the sails come in and eat them all.” Jon Whittle
Birds flocking around ballyhoo
To find the bait, Milazzo keys in on birds. “You might not see the ballyhoos actually jumping out of the water, but you know when you see the frigates swoop down,” Milazzo says. “Once you get close, you’re going to see the bait showering. It’s mostly sight-fishing, throwing your bait right in front of a sailfish’s face, which can be tricky.” Galyna Andrushko/stock.adobe.com
Sportfishing boat running out from Islamorada
Islamorada’s best-known launch point is Bud N’ Mary’s, an 80-plus-year-old institution located where the Atlantic meets the Gulf at Mile Marker 79. The marina offers access to some of the Keys’ most iconic fishing spots including Alligator Reef, the 409 Hump and the Islamorada Hump. On this mission, the fishing takes place with Islamorada’s low-rise skyline over your shoulder. Jon Whittle
Chasing a billfish in Islamorada
It’s a run-and-gun game. Chasing the feeding frenzy requires a breakneck race toward the action to cast on any sails visible on the surface. It’s a kinetic, frenzied way to fish, but the sight of black-backed billfish in 15 feet of crystal-clear water is unforgettable. Jon Whittle
Spotting fish from a boat's tower
Milazzo searches from the tower. For his mate, it’s a constant dance of letting out line and reeling it back in to allow the baitfish to stay just on or below the surface. Crews deploy a kite on either side of the boat, each one with three baits, setting out six rods to constantly attend to. Tip your mates well, friends. Jon Whittle

Read Next: Guide to Spring Sailfish Fishing

Throwing a cast-net at ballyhoo
Ballyhoo are known for their vibrant appearance and lively behavior, making them attractive to pelagics like marlin, sailfish and tuna. Anglers commonly troll ballyhoo or fish them live. Availability and effectiveness make them a favorite bait. After a few proper cast-net throws by Milazzo, the ballyhoos’ slender, silver bodies turn the livewell into a disco ball. Jon Whittle

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