A friend of ours was recently crewing on a boat from the east coast to St Thomas. They rounded the east end of the island just after midnight and the owner decide to enter Charlotte Amalie using his chart plotter. My friend was sitting n the foredeck as they were entering the harbor, when all of a sudden he saw they were headed right for some breakers and rocks. He ran back to the cockpit and grabbed the
wheel from the helmsman saving the boat from certain disaster. The owner had been down at the nav station watching the chart plotter and giving directions to the helmsman. Later they discovered that the chart plotter was using the wrong datum for the USVI. Chart plotters are not infallible.
When we were in Tahiti a number of years ago, a sailboat was attempting to enter Papeete at night and confused two
lights as a range marker for the harbor entrance. Unfortunately they were range
lights for a different channel and they ended up on the reef.
After 96,000 miles and two circumnavigations, Kitty and I have one hard fast rule; We NEVER enter any (strange or other wise) port at night. If we are not sure of making a daylight entrance, we always heave-to 30 miles from land and come in the next day. Even if it is rough weather, heaving-to is much more relaxing than the angst of trying to enter a port at night with your heart in your mouth and the fear of loosing the boat.