The Great Port Heist

Matis and Chekov and I will distract the Captain. You, Anne, and Henry sneak into his quarters and use Anne's lockpicking skills to get into the red cabinet on the left of the room. Grab the Port, pour it into a flask and replace everything you took with seawater. This won't deter him long but it'll give us a few precious moments between him pouring the Port and realizing that some of it has been replaced. Return with the flask and Henry will give the all-clear signal and boom, we're swimming in quality drink. There's no way this plan could go wrong.