Assassin's Creed 3 – Privateer Contracts: Saint-Augustine Contracts

Henderson in Distress
Optional Objective:
Limit ally health loss to 50%

When things start, sail directly into the ship to ship conflict. There are a total of 11 ships that need to be sunk. Start with the 4 that are very close by and use a combination of the broadside and swivel cannon to quickly reduce them to rubble. After that, the remaining ships will close the distance and come at the Henderson. Keep the Aquila between them and it. Some tight maneuvering and it will not be long before you have sunk all 11 ships.

Paving the Way
Optional Objective:
Destroy 3 ships by ramming them

If you  can spare £8,000, then getting the ram before this will make your life a lot easier. The optional objective here is easiest to do right at the start of the confrontations opposed to chasing things down later. Start with just sailing ahead and around the bend until the action begins. Start by going full sail for a minute to build speed then cut to half to aim and ram the ships. Doing this early is easier but it is riskier as the Aquila takes a lot of damage each time. It will survive. Mix with proper bracing and it will not be long (or hard) to finish off the 10 ships here.

Dread of the Night
Optional Objective:
Limit environmental damage to 25%

When the mission starts, do not worry about firing on the Saint James, simply worry about getting through the navigational hazards. It is not too long before you will get through the first area where you need to worry about the optional objective. Once that is complete, move to get a broadside shot at the Saint James. Mind you, this is after you run/ram the supporting ships. Now you have 13 ships to take down as quickly as you can. Mix between the swivel and the broadside. It will not be long before you sink the whole fleet and complete this section of the privateer contracts.