I personally love the freedom of driving. I find having a good map to be of help, but honestly, the best help is just asking as you go along, if you're wondering if you're going the right way stop when you see someone along the road and ask if you are on the right road to .....(wherever you are going). I was very intimidated when I first started driving in Jamaica, I remember very clearly my first time driving to Montego Bay and how I was so scared to do it, but then I got the hang of it, and part of it was my fear of looking stupid and having to ask if I'm going the right way...then I realized how many Jamaicans do it too. For years now I've driven all over the island, and done much of it solo, including kingston (which I wouldn't recommend unless you are familiar with it). For gas, just keep filling up between 1/4-1/2 tank and you'll be fine. As someone else said, keep valuables in the trunk. Get FULL insurance, even though you pay more, it's totally worth the piece of mind you get knowing you don't have a $1500 to $3000 deductable if something happens (and things happen easily to cars here as I'm sure you know). Also, keep in mind luggage space (this is something I always forget when renting a car somewhere else), make sure the trunk can hold the amount of luggage you and your passengers will have. The amount of freedom you'll get from renting a car rather than relying on other ways of transport will be worth it.