I've made the circumnavigation twice and loved every minute of it. We started in Negril both times. In 1985, we stayed in Mandeville, Kingston, Port Antonio, and Runaway Bay. In 1990, we skipped Mandeville and Kingston. I used to have a Dinner's Club card that covered the co0llision damage waiver, but I'm not sure any cards cover it these days. Jamaica, Ireland and Israel you're gonna pay for that insurance and the tire/wheel coverage is sound advice. That first trip, I drove 950 miles (not km) over ten days.
So many adventures. I copied some WW II topo maps from the university library and just explored. Roads that ended in jungle. Roads that ended in cow pastures and a little boy led us back to the paved road. Milk River to Alligator Pond in first gear. The botanical gardens in Castleton. Rafting on the Rio Grande without another raft in sight. The boy who ran down the bank, dove in and swam out to us underwater holding a bouquet just above the water. A stop for a delicious meal over a fire and buying a duck carving. The two women with laundry baskets on their heads and little ones clinging to their skirts, who helped us find our way somewhere in the middle of the island. "Yes, keep on," and as we pulled away, "Enjoy your stay!" Oh, we unforgettably did.