Most will, yes. Most can take a track log of someone walking in a closed circuit (square, circle, or any other variety of out/back) and then compute the square acres or square miles of your journey.
This isn't something that I've done often, so there could be a better way to do it, but yes, you can do it from data collected on the PN-20. I walked a loop the other day and collected the tracklog from that loop. Now since the GPS position doesn't actually "close" the loop since it is hyper accurate, I created a new draw layer within the PN-20's included topo usa software. From there I traced the tracklog with the line tool and then when I "closed" the line back on the starting point it gave me the square footage as well as square acres of the loop I walked.
There might be an easier way, but this isn't something I do that often. It can be done, however.
It is easier too if you are working with straight lines. Just create a waypoint at each of the corners of the location you are measuring (even if there are more than four corners) then draw a line to each of the waypoints you marked.
If you are trying to survey a property (for example) that would be a more accurate way to do it anyway.... go to one of the stakes, create a waypoint, let the waypoint average for a few minutes, save the averaged point, then move on to the next point. Once you are done you could create the lines between the points from within topo usa and have a good estimate of square feet, acres, etc.
You could create the waypoints on the TomTom and then use some other program to import the waypoints and calculate the area. However it will not "average" a waypoint and thus each location might not be as accurate.
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