Name what countries you would reach first if you left in every direction, from anywhere in Florida. (excluding USA)
You can't go over the US to reach other countries.
From Google Earth, it looks like if you left Pensacola at a heading of 291.38 degrees, you would hit Papua New Guinea before hitting any other country (besides the US). In fact, it looks like any heading (from Pensacola) between 282.90 degrees and 312.69 degrees would miss both Canada and Mexico and would make several other countries in Oceania reachable.