Using a plastic boat to chase sheepshead is an ideal method for taking the fight to the fish, especially during periods of low tide when overhead clearance under a pier or dock is maximized.
Kayakers have an unusual advantage over power boaters when fishing docks in that the whole vessel will often fit underneath, allowing anglers access to the furthest reaches of the underside that rarely see a hook. Moving from pier to pier is also much easier if the angler starts upstream and allows the current to push the boat to the next piling.
Paddlers often report days where they could sight-fish right under the kayak, picking sheepshead off the rocks or dock structure as they slowly paddle along. The ability to maneuver the boat directly over the top of the fish is also an advantage when it come to setting the hook, as sheepshead frequently follow a bait down to the bottom and pick at it with their teeth from above.
A vertical hookset, hopefully into the fish’s mouth, increases your odds of connecting, but when sheepshead fishing, there is no guarantee.
When fishing around piers or docks, water may be too deep to reach with a stakeout pole and too cumbersome to tie off or anchor. Alerting the fish to your presence is also a concern. A useful do-it-yourself hack for securing the boat long enough to jig a bait around structure is to use a spring clamp on a 6 foot tether tied off to the boat. Simply attach the clamp to a frame member and start working the bait around everything within reach. When it’s time to move, unpinch the clamp and scull over to the next spot.
Regardless of what type of boat you may be in, a rising from low tide is often best, because it starts covering up more structure with less flow. Either end of the tide cycle can be productive, but the more current there is, the more weight is needed to stay in contact with the bait and the better chance sheepshead have to steal your bait.