Hello,
My GF is originally from St Thomas, USVI (she now goes to Med School in the states). Just a quick seaplane ride away.
Ive never been to anywhere except the airport in Puerto Rico, but if its as hilly and driving as severe as St. Thomas, I think that a 40 weight - preferably a 15w40 diesel spec oil would be best. Look for chevron delo 400, mobil delvac 1300 super, shell rotella or texaco ursa.
Usually I dont think a 15w40 oil is necessary, but down there, where the oil never goes below 80F (well, once in a while it gets to 65F), driving right after startup includes either a lot of engine braking or hill climbing, and some of the terrain is really steep and hard on an engine, I think that a 15w40 is the best dino oil to deal with the thrashings the cars take.
How many miles do you usually get out of a car down there? In St. Thomas, it tends to be pretty low by US standards.
JMH
P.S. If it has an automatic transmission, change the fluid OFTEN. My GF's 4 runner, which is the car she has for when she goes back home, has some problems with the fluid overheating, boiling, and doing weird stuff, due to the steep hills.