Jack looks it over carefully, and decides he could break in through the roof if he wanted to, but it would take about 5 minutes and be somewhat noisy. He'd need some sort of equipment, such as a saw or crowbar.
Bashing through the door might be easier, but he's a lot less visible up here.
The other party members are fully organized and ready for a fight. Seems to me you have several choices:
1 Charge the fort, a la the light brigade.
2 Charge the docks, hoping to eliminate the two clusters of pirates there before the main force can intervene.
3 Harrass either target while trying to avoid a conclusive engagement.
4 Retreat, hoping they will follow.
Let me know a general strategy, I don't think going round by round, action by action is fruitfull at the moment.