Assassin's Creed 4: Black Flag Walkthrough Part 28 – Sequence 5: “Traveling Salesman”

Optional Objectives:
Kill 4 Gunners
Kill 5 Guards stunned by smoke bombs

Head on out to Kingston and speak with Adewale on the beach to start up this memory. Start by using Eagle Vision to mark your targets. After that head for the nearby ramp and climb to the upper branches of the nearby tree. This will put you in a position to keep after them without much worry of them spotting you.

Run from the tree up to the bell tower and out to the side of it. Just keep them in view to avoid losing them. Wait for them to leave the bell tower then dive down into the hay cart below. After that head straight out from the bell tower and clamber up the nearby building. Continue to the North and go through the trees after the building. On the far side you will find a Gunner you can kill without drawing any attention.

Continue to the North again after that. Go through another set of trees then pause of the rooftop. The proper place is marked with Pirns and Torres moving into a garden with 2 Soldiers at the entrance. Wait on the roof. They will head in a direction and pause. They will have some discussion then turn to the South. Follow them as they do so. Try to avoid the Restricted Area as it will slow their progress. Take to the rooftops and then follow them as they turn to the West. There is another Gunner along this path so find him and kill him. You are most of the way through the first Optional Objective.

Just keep following them as they go to the West. You will dive from the rooftops down to the haycart below you. From there slip into the Restricted area when no one is looking to start the eavesdrop.

With the eavesdrop you will want to move in close. Head over to the West, using the Stalking Zones and the haycart (for a quick assassination) to reach the buildings and climb up again. Once up there, head to the North briefly then track down the final gunner. Now you just need to slip through another Restricted Area.

From where you killed the final Gunner, turn to the left and perform a leap of faith into the hay cart below. After that, kill the nearby guard then duck out of it so you can make for the Stalking Zone. Now dart from there to the Stalking Zone across the dirt path. Keep in this direction until you are next to a large plaza with guards ringing it and Pirns  and Torres stopped again.

Things take a turn for the worse here as Pirns reveals that he knows they were followed. Equip your smoke bombs and throw one down. Use that time to quickly take out the guards who have come at it. Throw a second as the cloud starts to break up.

After this, you need to keep after James Kidd who is running away and very determined to get his 2 targets. You need to chase him down. While it is tempting to take off after him on the rooftops, it is much easier to tail him on the ground. When he jumps down to ground level, you are in a better position to catch him. He will also get caught up in a fight with some Soldiers. Drop another Smoke bomb, take out the Soldiers then Tackle Kidd. Remember tackling has to be done in High Profile. Do that and you will finish out the memory.