You must first complete Sequence 3. Then you can go and talk to Ned Wynert, and five new types of Activities will appear on the map:3 that count towards this achievement
- Cargo Hijack
(need to purchase Ale Heist gang upgrade)
- Train Robbery
- Boat Raidand 2 that do not count
- Smuggler's Boat
- Cart Escort (aka Escort Friendly Cargo Shipments) (need to purchase Ale Heist gang upgrade)
From the map press
to show the Legend, to see the icons for each of these Activities.
Successfully completing Cargo Hijacks, Train Robberies and Boat Raids
will give progress towards this achievement. More than 10 Cargo Hijacks are shown at fixed locations on your map, and these are non-repeatable. More Train Robberies and Boat Raids will appear at random.
Train Robberies are the easiest, you have to collect 3 or 4 pieces of treasure and it doesn't matter if you get into a fight.
For Boat Raids you need to get the manifest from one of the enemies, and then mark 3 pieces of cargo before the timer runs out.
For the fixed location Cargo Hijacks it is best if you first kill all the enemies without being detected, before you get in the Cart and take it to the destination.