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Scott,
It's not surprising that you're getting mixed results. Chart plotters simply aren't set up to accurately compute bearing and distance over long trajectories. Bermuda is almost 600 nautical miles from Cape Lookout.
The best way to obtain bearing and distance between any two geographic points is to use a calculator for Rhumb Lines or for Great Circle Bearings, as desired. You can find these calculators online or a part of many navigational programs, or you can extract the formulae from any navigation text and do the math yourself.
If you choose the two points you have mentioned....
Cape Lookout (actually, nun/bell buoy R14) at 34 deg 18.15N 76 deg 24.21 W
and
SW tip of Hamilton Bermuda (this is approximate...I don't have a nautical chart here for Bermuda) at 32 deg 14 min N 64 deg 53.3 min W
then
the Rhumb Line bearing is 102.1 degs true and the distance is 590.8 nm.
The initial Great Circle bearing is 98.9 degs true, distance is 590.5 nm.
Also, be sure your GPS is reading True if that's what you want. The default for most GPS units is magnetic, not true.
Bill
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