Open the map image in Ps and duplicate. Turn the original layer off.
Select your Brush Tool.
Open your Brushes Panel.
Choose the size of the dot you wish, I used a 5px dot here, larger for demonstration.
Set your spacing for the dots. I used 175%.
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Create a new layer above the duplicated map layer.
Select your Pen Tool.
Click on the starting point of your dotted line. (Florida)
Click on the ending point of your dotted line, (England) hold the click and drag the handle to create a suitable curve to your liking.
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Right click and select "Stroke Path".
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Then choose Brush and check off "simulate pressure".
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Hit enter to make the Path invisible. You should be done with this "flight path"!
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Add more Flight paths on separate layers.
Here's a SS of my layers panel. Be sure to name the flight path layers.
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edit:
Here's the way I would do this.....
When you set up your brush, also check "Shape Dynamics", then when you stroke your path, check the "simulate pressure" on.........and you get a nice tapered dotted path.
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