Sailfish are considered one of the most sought after game fish in the Florida Keys. They are occasionally caught year round in the waters around the keys but the best time to fish for them in winter months. Sailfish run in small groups and singles and tend to congregate just outside the reef line in the winter. They can be caught trolling but most people in the Keys fish for sailfish with live large pilchards or ballyhoo. They either drift or slow troll around the edge of the reef and over wrecks that located in water beyond where the reef drops off.
Best tackle in my opinion would be a spinning reel loaded with 20 pound line, then a few feet of 50 pound fluorocarbon leader, and then a 7/0 or 8/0 circle hook.
Sailfish are known for making great runs and numerous leaps in the air when hooked. They tend to hunt by sight and its is pretty important that your bait is swimming strongly and will react when it sees the sailfish coming. A really weak or dying bait tends not to work as well in any fishing, but even more in the case of sailfish.