This is all the crap my SO took with him on our trip around downtown. I took my purse.
We went to Whole Foods because I am obsessed with their bakery. He was a little paranoid because bikes are stolen from there often, even though it is a well trafficked spot. Of course, you'll find some of the most expensive-looking bikes in Austin on those racks. (I will not pretend I am up to date on the going rate for nice bikes) I believe he triple locked his bike. I had my trusty Kryptonite and mace.
It was funny seeing someone who rides only for training purposes ride for pure pleasure. He wanted only bike lanes and chided me for acting too much like a car. (But I had plenty of time to make that left turn! I really did) Obviously, I have some work to do on the baggage part, although the next time we went out he did go sans helmet.