If you have the proper equipment, arriving at night is not much different from arriving in daylight. It just takes a different set of interpretive skills. I have radar, a chatplotter and sonar and I also have a bow mounted LED GoLight that is remote controlled with a hand held controller. This assumes of course that you have studied the charts before hand and have a good idea how you intend to navigate before arriving. If you wait until you get there, the situation can get complicated fast. If so, then just stop and regroup.
On a trip down to Florida in 2013 from Kentucky Lake to Mobile, we arrived after dark on the Tenn-Tom at Midway Marina, Columbus Marina, Bashi Creek anchorage and Turner Marine at Dog River. This was 4 out of 9 nights of travel. On the Tenn-Tom, the luck of the locks determines your schedule. One day, we lost 2-1/2 hours to delays at locks. We used all of the electronics and the GoLight with no problem. The GoLight beam on a buoy or marker makes it really shine. Confirmed by radar, both add greatly to your situational awareness.
On our crossing from Panama City to Clearwater, we also arrived at Clearwater Pass and Clearwater Marina after dark. From there down the Intercoastal, we arrived at Venice and Fisherman's Village At Punta Gorda after dark. In addition to the electronics, I have a full enclosure which takes the weather down to an extremely manageable level. I also run my generator while not at the dock and keep my HVAC operating as well as our salon lighting. This keeps my wife comfortable and she is either reading or watching our satellite TV. If I get cool, I open the companionway doors and stand in the companion way and steer using my hand held wireless autopilot controler. I turn most of the lights off in the salon when I approach land, but on the Tenn-Tom and Intercoastal, I just close my ompanionway doors which reduces the strain on my night vision. I also have a DigitalYacht IAIS which transmits wirelessly to my IPhone and IPad thru INavX. I use either to monitor other tows and plan my passing spots if on a waterway.
Personally, I would just as soon travel at night as in the daytime as long as my electronics are working. It may take you a little practice to get comfortable, but once you are used to it, it is like driving a car at night. There are just a different set of ques to watch. If you lose your bearings, just stop until you get back on track. After all, a sailboat is not moving very fast so in most situations, you have lots of time.