I think you could do it early in the morning before all of us tourist got on the road. It would not be a bad idea to have some one drive behind as shield.
However, I would suggest it is time to cross train - drop her at Maho and let her swim to Hawknest in and out of the Cinnamon and Trunk. That is 3.5 miles and would give her a pretty good low impact workout. Shoot for a 1.5 hours.
Plus she will get to see some neat things along the way. Here again a kayak chase boat probably a good idea.
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