The law says prescriptions must be in their original bottles. Actual experience is many people travel with their prescriptions in a daily pill organizer and don't experience any issues. Personally, I have no concerns traveling domestically with prescription meds in a pill organizer, but I always travel with them in the original bottles when traveling internationally, including on cruises. I bring the empty pill organizer and fill it after arriving at my destination. I don't want to take any chances when going through customs.
We do this as well. Also, I bring an extra week's worth of meds in case there are delays or other issues that force me to stay longer than planned. I figure/hope if I will be delayed longer than that I can either have more meds shipped or get an Rx locally.
I take a lot of rx meds and even more prescribed non-Rx meds and supplements. Anything that is a "medication" (Rx or OTC) lives in its original bottle. for the meds I get that with normal 90 day supplies are in huge bottles, I have asked my pharmacy when doing a refill to also please include a small empty labelled container for when I travel. They have done so without issue and I reuse those smaller bottles from trip to trip. For OTC meds that come in huge bottles, I bite the bullet and buy one more appropriate smaller sized bottle and I just refill it for traveling as needed.
For the supplements, most of them come in glass bottles and I am not about to travel with the bottles due to weight, bulk, and the possibility of breakage. For those, I do two things, one they go into small medication baggies (ziploc snack-size baggies will work too) that I have printed a label for (manufacturer, product name, dosage per tablet/capsule/gelcap); and two, I used MS Word to create a 4x6 card with a picture of the med bottle and ingredient info from the manufacturer's website. I printed those on 4x6 photo paper and they all go in the container I use to hold all the baggies. While there is a risk with this, I feel it strikes an appropriate balance between carrying glass bottles and some kind of more sane approach. I have not had any issues, but realize there could be.
Once I arrive at my destination, everything goes into the empty pill organizers; I do a week at a time, so will reload if we have a longer trip.
Some tools I found very helpful for doing all this:
LLBean has fleece-lined organizers that are a great size and that give a bit (but not too much) of padding to help protect bottles; I use red ones as in my packing red = medical and helps organize things:
http://www.llbean.com/llb/shop/7689...ee&attrValue_0=Mountain Red&productId=1274603
I used to put the bottles loose in that bag but it is actually somewhat frustrating once you get too many as you have to paw through 'em to find what you want. So I now organize them (e.g. daily meds in one; as needed meds in another) in these little sacs from RuMe, which are just the right size for holding several small Rx pill bottles "upright" (and they won't roll around and rearrange themselves

):
http://www.myrume.com/collections/organizers-and-accessories/products/reveal-pocket
The RuMe pockets with the Rx bottles in them then goes into the LLBean organizer -- things stay a bit neater and it is much easier to get to exactly what you want.
SW