When operating a small powerboat in Boston Harbor, one has to be careful of the wake that a larger boat creates at full speed. This could not be more true than when dealing the the vessel Massachusetts. I like this boat and commute on it regularly, but I will point out the fact that it displaces quite a bit of water and makes a HUGE wake.
When overtaking a large vessel, I find one should treat its wake like a following sea. The further you stay behind the stern of the vessel you are overtaking the better- and be careful not to go so fast as to bury the bow in an oncoming wake. Proper protocol is to hit one short blast of the horn if passing to starboard, two blasts if by port.
Check out this video of this unfortunate boater trying (unsuccessfully) to pass the Massachusetts.
The vessel Massachusetts: