Assassin's Creed 3 – Naval Mission: Biddle's Hideout
Before you start this mission, it is highly recommended that the Aquila be as upgraded as possible. Having the extra cannon and heat shot will make this mission much easier (and the optional objectives far more plausible).
Optional Objectives:
Take out the Man-O-Wars within 3 minutes
Destroy the Randolph's mast with a single broadside
Kill only Biddle
This mission will start slow but it will begin with a bang. Head forward after having Connor run back to the wheel and take it. For now, just focus on pursuing the Randolph and do not worry about firing on her. It is only after a few other things happen you will need to worry about the Randolph in full. Once the call rises for the pair of Man-O-Wars that appear to attack the Aquila with the Randolph that you need to worry about that boat.
When in this skirmish, watch your shots and check your fire. The seas grow very choppy quickly making it harder to land a clear shot but getting close always increases the chance of more shots landing. Start by equipping Heat Shot and getting into broadside range with a Man-O-War. Once there aim and fire. A good broadside will expose the weak spot which can then be targeted with the Swivel Cannons and quickly sink the ship. Worse case is you need to make a second run on the Man-O-War. With the extra cannon and heat shot, it takes 2 broadsides to sink a Man-O-War.
Once you have dealt with the Man-O-Wars then change to chain shot. It is time to get the Randolph and disable her. Close in on her and fire off a broadside of chain shot. Done properly it only does take a single shot but most of the chains need to hit for it to work.
Once the Randolph is disabled, switch to half sail to bring the Aquila around then ram. Now Connor has a real challenge. He must break from his immediate fight and sprint for the stern of the Randolph. Once Connor approaches Biddle, the fight changes to just them effectively. As Biddle attacks, use a Counter-Disarm to render Biddle vulnerable. From there launch into a combo. Once he blocks one of those strikes, break his defense to get another opening (or wait for him to attack again and once again disarm him). Just keep this up until the battle moves to its second phase.
Biddle and Connor are below deck now. Run into the room Biddle ran into. Position Connor near 1 of the 3 barrels in this room. From there Connor can smash him into any of those 3 barrels. From there, just attack him as he provokes you. Use the Weapon Swipe as needed to ensure that Biddle does not fire his pistol at Connor too many times. Just enjoy the fight.