Sailfishing the edge that made Islamorada famous.
Islamorada calls itself the sportfishing capital of the world, and the winter sailfish run on the reef edge is a big part of why.
When the first cold fronts push bait down the reef line, the sailfish follow, and the stretch of edge off Islamorada becomes some of the best billfishing in the Atlantic. Tailing fish ride the swells after a front, and on the right day you can sight-fish them like a flats guide.
We fish them the classic Keys way: kites and live bait along the color change, pitching to fish when they show. The jump sequences are unforgettable, and every sailfish is released healthy to fight again. Plan a three-quarter or full day so the spread stays in the zone through the tide changes.
A note on the fleet's pedigree
Capt. Skip Bradeen, one of the collective's captains, has half a century of Islamorada charter history and was voted best captain in the Upper Keys 14 years straight. Sailfish season is when that experience pays.
More sailfish from our decks
Every frame below came off one of our boats. Tap a trip together and add your own.
Quick answers
When is sailfish season in Islamorada?
Winter, roughly December through April, with the days after cold fronts often the hottest bites of the year.
Do you release the sailfish?
Yes. Sailfish are released boatside after photos. Bring a camera; the jumps are the trophy.
How many people can fish?
Up to 6 guests on either Hatteras. Kite fishing rotates anglers through the fighting chair so everyone gets a turn.