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.
by Robb December 24, 2003
Get the sailing with the captain mug.I was sailing with the Captain, he'll show me the sights, I wish tomorrow morning would be as good as tonight
by btm321 December 1, 2010
Get the Sailing with the Captain mug.