Mom, I understand your angst. But here聮s my advice: Relax a little. I assume your son is a competent cyclist, or else he would not be attempting such an ambitious聟uh, wait. Did I read this right? January? As in, the month that follows December?
Apple iPhone
iPhoneYou cannot bicycle cross-country in January. Not even if you do the Florida-San Diego route, via Mexico. There聮s too much chance for lousy, cold, snowy weather, not to mention the lack of daylight. Did I comment on the snowy weather? And the lack of daylight? Seriously, I don聮t think anybody in their right mind tries this before May. It聮s simply too hard on its own, without adding the impediment of having the weather gods all arrayed against you.
So once you get him to agree to a May start, then we can talk. My own feeling is that a good wireless phone and charger is more than adequate. Get him an iPhone ($199 with contract)聴it聮s cool and it has e-mail, maps, and GPS. He calls every day at 6 p.m. or you promise to hunt him down. You are Mom, he will listen.
Other advice: Buy a copy of Barbara Siegert聮s ($14), a good guide to this trek. Get him a trailer ($329), which will work much better than using saddlebags (a.k.a. panniers). Make sure he has lights聟lots of lights. Otherwise, he聮s young and there聮s not much he can聮t endure. But have a one-way plane ticket stashed somewhere. Many a strong person has bailed on this effort.
Otherwise, let him go. Bicycle accidents actually are quite rare. This is safer than sending him cross-country in a Ford Mustang. But dear Lord, not in January!
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