Here's a teaser on the Port Attack feature (to be added in a not too distant new version of the game).
The port attack implementation aims to provide a simple and swift resolution of such battles, but still provide the player with some meaningful and hopefully interesting gameplay choices. Port attacks will usually require large crews and the really big ports (Havanna, etc) will be pretty much out of reach. There will be various features added later (traitors, intelligence gathered during interrogation, fleets, etc) that might be used to place even these powerful locations at the risk of being sacked. But that is stuff to be added in a later iteration.
The following is the first draft of the in-game help file - this should hopefully give you a pretty good idea of how the port attacks will work. As always, feel free to comment.
Port Attacks
You have decided to assault a port. This will result in a battle
between your crew and the enemy guard force. At it's core, this is
a series of competitive dice rolls, but the battle goes through
a number of phases in which you will be able to make a series
of decisions.
Purpose
At the start of the battle, you get to chose what the purpose of
your attack will be. Your options are:
Plunder: You're here for the gold and goods.
Destruction: Your aim is to cause as much destruction as possible.
This has two effects if you are successful; it earns you double emnity
from the targeted empire, and make a latter attempt to conquer the
region easier (you burn the forts defending the town).
Conquest: Your aim is to capture the region for your patron. This
is extremely difficult without a crushing superiority over the
local garrison.
Tactic
Having chosen your purpose, you then get to choose what method you
will employ to carry out your mission. Your options are:
Charge: This is the default approach, devoid of finesse or fancy
tricks. Point your men at the enemy and the rest will sort out
itself.
Surprise Attack: A surprise attack matches your ability to control
your men - determined by your Charisma - against the alertness of
the enemy garrison.
Flank Attack: A flank attack matches your Cunning against the Cunning
of the enemy garrison commander. If successful, your outflanking
force (30%) will fight with triple strength during the rest of the
battle.
Surgical Strike: The attack will be limited to a quick hit and run.
This increases your chances of success, but reduces the benefit of
your success (i.e., if you are plundering, the attack's chance of
success is increased, but the plunder you gain will be reduced).
Retreat: Chose the better part of valor and retreat. Your crew will be
unhappy.
Battle Event
Once you have chosen your goal and tactic, the first round of the
battle is fought. Each side scores a number of "hits" on the other
side (which results in casaulties). If either side scores double
as many hits as the other, the losing side is instantly routed.
Your chances of scoring hits are improved with a high Fencing value
(as is also the case with boarding combat.
A successful surprise attack will reduce the strength of the
defenders in the first round of combat. The effect depends on your
leadership abilities, but can vary from -10% to -30%.
An attacking force that tries to flank attack will detach 30% of its
force to the flank. The remainder of the force will face off against
the garrison during this period.
Depending on the situation in the battle, a battle event may occur
after the first round. This will usually be some situation that has
occurred during the battle, to which you may have the opportunity to
react; depending on your reaction, your or the enemy forces may gain
a bonus for the rest of the battle. Often, you will have the opportunity
to retreat your forces at this point.
Battle Conclusion
Once the battle event has been resolved, the second round of the
battle is fought. If the outflanking attempt succeeds, the flanking
force will now join the force with triple strength (if the outflank
fails, they will rejoin at normal strength).
At this point, the side that has scored the most total "hits" wins the
battle. If you chose to plunder the town, you now receive your well-earned
loot. If you chose to target destruction, the game now resolves the
effects of the destruction. The greater the victory, the more
devastating is the effect of the destruction. You also gain a little plunder.
To capture a region, it is not sufficient to just win the battle. Under normal
circumstances, you will have to score twice as many hits as the defending
force to conquer the region. If the defenses of the region have previously
been damaged, this requirement is reduced dependent on the previously
inflicted destruction in the region. A captured region is turned over to
a governor of the empire you are fighting for. Loot gained during
conquest is also minimal compared to a regular plundering mission.