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I have been cycling a lot, 550 mile trips, over 1700 miles this year. I will also be supported most of the time (daughter, wife). I will have to self-support for a bit.
My experience is that riding every day reduces insulin needs, but can increase frequency of changing infusion sites. Carrying lots of cliff bars and fig newtons to deal with hypoglycemia has been effective.
Resupplying insulin should be possible. My endocrinologist will give me written prescriptions to carry and even if I can't get Medicare to cover it, I'll just pay for it.
I guess my worry is how my body will cope with riding day in and day out for so long. In October, we are riding across North Carolina --7 days, 550 miles-- with real mountains so I should get an idea what that will feel like.. My sense is that if I can do this, more will be possibleI think that if you ride sensible for you daily distances you will be fine. Do be careful with managing your diabetes though as there are some pretty remote places where getting in trouble has higher penalties. On the other hand in the more remote sections of the Southwest most people will stop to assist if they see someone in trouble.