Frankly I love driving in Jamaica. In fact my wife and I just "closed the gap" by driving and circumnavigating the entire island. We have been to Port Antonio on the north road, and Kingston on the south, but we just needed to close the gap from Kingston to Port Antonio. We left Negril driving the south road to Kingston and then followed the coastline to Port Antonio (anybody wishing to do that please be aware, the road between Kingston and Port Antonio is very very poor. 131Kms of new construction underway and just bad roads, 1/10 or even 0/10). BTW we drive an open air, top down arms out the window vehicle and never felt threatened, maybe even the other way around. We felt safe every where we went.

Orange Bay and even Orange Hill we have driven may time and no threats there at all. I think what happens is, there is a protest or incident that happened in a place like Orange Bay, it gets put on the list of "do not travel" and it kinda stays there forever even if it's the nicest most friendly town. I'm not saying driving in Jamaica is totally safe, I'm just saying take it easy, don't drive like others on the road, and be careful. If you rent in MoBay, the drive from there to Negril would be a nice ice breaker. If you can manage MoBay, Hopewell and Lucea then you should be able to drive anywhere.

Take it easy, don't watch the guy in front, watch the guy several cars ahead, and remember, DRIVE ON THE LEFT SIDE OF THE ROAD!

P/S The only reason I wouldn't drive in Whitehall is, after you get in you might not get out. It's hard to navigate and you might end up driving passed the same domino's game several times. LOL