I do this for all of my randonneuring rides. Jeff and several friends always know my route, and then I post my progress at every controle. Sure, sometimes it's hours between each check in, but I think it gives them some comfort when they see a post from me at 3am that I'm still alive and moving forward.
Something else I've just done this week is to enable the "where is my iphone" app. It should allow Jeff to log in and see where my phone is. It was designed to help you find a lost or stolen phone, but I imagine it will be useful if he wants to see where I am at any given moment, assuming I have cell service (which I often don't on the more rural legs of my ride.)





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