sailing with the captain
To drink large quantities of Captain Morgan's Rum, usually with a group, and hopefully to the point of oblivion.
That girl I hooked up with was so fugly that I had to go sailing with the captain before I could bang her.
Sailing with the Captain
A Song by the Celtic rock band Dust Rhinos about Drinking lots of Captain Morgan Rum
I was sailing with the Captain, he'll show me the sights, I wish tomorrow morning would be as good as tonight