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I never take the bottles - I just take Lenny's pill pods filled with his meds and I wrap his meds list around it (yes, he's on that many I have to have a list of them) and I put all of that in a ziploc and then tape it shut so nothing comes open. I've never been questioned on it.
I take mine in my weekly pill case. I duck tape the cases closed and then put it in a zip lock. I have also learned the hard way to bring several extra days worth of medicine with me. I got delayed on my return once and ran out of meds.
I always use the weekly cases when we travel and I have never had any issues. The only time I took the bottles was when I traveled out of the country and when my Grandmother was taking a narcotic. We always pack 2-3 day extra supply in case of delays or if anything would drop etc. As far as needing additional prescription while on vacation as long as you have the drugstore name & number they can electronically transfer it to another pharmacy if need be.
I also always use the pill cases and have never had a problem. If you are concerned, you can ask your pharmacy to give you extra labels like they print for the bottles and carry those with you. We did that when traveling overseas just for our peace of mind.
We are back. I had no issues with the weekly pill cases. They helped us stay on track with meds and security didn't question it at all. I did bring extra meds in one bottle just in case and that was fine too.
Our lunchbox cooler with an ice pack and my DDs injection that had to be kept cold was pulled for extra screening even though we had alerted the security staff that we had it. We certainly didn't mind though. I prefer they check anything they think is suspicious.