If the destination is close enough to get there in daylight hours, I leave early enough to get there well before dark.
If not, I leave late enough in the evening to sail comfortably through the night and get there at daybreak.
If the voyage is longer than 24 hours and my ETA looks like being in darkness hours, I slow the boat down to stage the arrival at daybreak anyway.
If all else fails, I stand off until daybreak but I don't go into a strange anchorage in the dark no matter how well lit or charted. When I'm close to things that can sink my boat, eyeball navigation has no substitute
Chart plotters may be pretty good these days but they're still plotting on images of
charts that are often nowhere near as accurate as we would like and unless you have the latest editions, they may contain inaccurate info.
JMHO
Andre