In celebration of my birthday, my wife and I took a train trip through four states using three train lines, a ferry, and a couples buses. We stayed in Port Jeff and Montauk (Yes, Eternal Sunshine of the Spotless Mind, end of the world, Montauk).
Besides some backup socks and boxers I threw in my wife's bag and what I normally carry on me, I brought my cellphone, eyecare, and paper/pad -- that's it!
Why? Simplicity. I always wanted to try the life of a hobo without baggage and this was the closest I could get for now.
Leaving the house for a four day trip without a bag made me feel like I was forgetting something, but I soon got used to it. It was glorious!
No unpacking and repacking in each hotel or deciding what to wear each day. I didn't have to lug anything around on public transportation or take stock of my belongings.
True, the experiment might not have worked as well if I wasn't able to steal my wife's toiletries or if it was hotter weather. I would have had to spend more money on t-shirts and toothpaste along the way. But it worked so well that my only regret was bringing as much as I did. The cellphone was a distraction and I hardly used the notepad. Next time it will just be the glasses.