While the post office says they will hold mail for only 30 days, the "hold mail request card" also says they won't resume delivery service until mail has been picked up. I have routinely stayed more than 30 days; I think this last trip was 36 days. USPS has put themselves in a bind. They won't hold beyond 30 days but they won't resume delivery until you pick up. So . . . they continue to hold. They have never said anything when I go to pick up.

As far as bills go, I have everything on auto pay except for my Visa bills. I pay those over the internet when I am on island.

If I have meds that expire, I contact the insurance company prior to departure and request a "vacation exception" and pick up refills before I go. I did once have to get a refill of one while on island, and Simpson Bay Pharmacy couldn't have been more accommodating. I asked for just enough to tide me over until I was back home.