Same here - I've done this on the 305. I used a marine mapping software to plot my course given coordinates, then fine-tunned it to my liking. The software is Coastal Explorer and the demo version is perfect for kayaking (and free, no time limit). Can use NOAA free maps too (great coastal coverage in the US and many other places). Out of that software, I generated a KMZ file that can be looked/tweaked in Google Earth, then as suggested, used that converter to save in the Garmin format, then imported through Garmin Training Center.
I suppose I could have skipped the first step and go directly to Google Earth, but my mapping software allows me to estimate my speed and also gives me tides and marine charts with buoy, depth, and other relevant info for navigation by compass for instance (bearings etc.).
The whole process may seem comlpicated but is very quick, once you have done it once or twice and write down what you do so you don't forget it for the next time -
It worked well - the Navigation feature on the Garmin 305 (and I assume 310 is not much different) is rather weak, but still useful enough to tell you the direction to go to. That was enough to allow me to follow a straight line to a finish that I did not know exactly where it was (the last 2-3 miles I would have been going blind otherwise and possibly in a curve as many others did, not being able to see the finish).
Don't know if being on a Mac has anything to do with your problem though - I used Windows...