Single Engine Piston, Caribbean Flying Advice

I guess over land you avoid any sort of mountainous terrain, lakes, cites and just constantly fly over runways?

Nope, in a single piston I was equally stressed over the mountains, in every other scenario you listed there's likely some kind of option if things go bad. I haven't spent any time over the Great Lakes, but you'd be equally F-ed there too. I also had a healthy amount of anxiety over my first Pacific crossing, just because of my unfamiliarity with it. There's nothing wrong with respecting the amount of risk you are putting yourself in, in my mind it helps to stay sharp and keeps from getting complacent.

Maybe I just don't make a clanging noise when I walk like you...
 
If I had to ditch in the great lakes this time of year, I think id prefer a crash axe to the side of the head
 
I was more referring to the fact that you probably won't survive a ditching attempt (head trauma, unconsciousness, or just inability to get out and drowning).

Back to Carribbean pertinent info for our good buddy Stomp.
 
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