Each convoy has its own captain, and each captain has 6 abilities. This may unlock naturally as you progress through the game but may require some grinding, as each ability takes a long time to rank up. It is a good idea to wait until late in a game before grinding this, as you will find many of the captain’s abilities will have ranked up naturally over the course of the game. You can view your captains and the level of their abilities by pressing and selecting each convoy on the list. You can always add and remove different ships within a single convoy, just remember that each time you add or remove ships you ensure that the convoy itself is never disbanded.
The captain has 6 abilities and each ability has a maximum of 5 points. Below is a list of the abilities and how they can be increased.
Battle experience – Increased by winning naval battles. This will increase as you progress through the game. NOTE: It seems only battles against other ships increases this, not attacks on towns and hideouts.
Navigation – Increased by sailing the seas. This can also be increased while on an automatic trade route and will probably be the first to reach 5.
Trade experience – Increased by trading goods with docks. This can also be increased while on an automatic trade route. It is a good idea to swap a convoy to a trade route if you don’t need it for battle.
Ship Building – increased while the convoy is being repaired in town. As you fight pirates or enemy convoys you will find yourself spending time repairing your convoy afterwards.
Combat Experience – increased during boarding fights. To ensure this doesn’t become a grind, try and use the same captain/convoy each time you need to capture an enemy ship.
Visibility Range – increased while a ship is on patrol. This is likely to be your last skill and will require grinding. TIP: To boost this, leave your convoy on patrol in the top right corner of the map as they shouldn’t be bothered by anyone.
TIP: You will find that over the course of the game many of the passive abilities like ‘trade experience,’ ‘navigation,’ ‘ship building,’ and ‘visibility range’ will upgrade while a convoy has been on an automatic trade route. So if you are planning on engaging in battle, be sure to swap the captain from your trade convoy to your warship convoy.
You will also encounter people in taverns across the Caribbean that will offer to improve your captain’s abilities (as long as his convoy is docked in that town) in exchange for gold. Unfortunately the price will be scaled depending on your rank and total worth, and will always be extremely expensive. However if you have maxed out the majority of the skills, save your game and buy the remaining skill points to unlock the achievement then reload to save the gold.
NOTE: This achievement is known to be glitchy for some and will occasionally drop your skill points for no reason. At the moment there is a known solution but the best advice is to either try a different captain or focus on raising the skill via teachers quickly.