The most memorable time on the streets busking for me was when I attended the Ferra Buskers Festival in Italy. Every night we would have hundreds of people dancing around us and we made lots of friends from all over the world. There was a great sense of freedom for me all week.
Its usually when I forget to plug my guitar in! lol
My first acoustic guitar a Yamaha APX10 was robbed on me in the streets of Dublin in 2010. i was playing at a charity busk event on the street and interestingly Gavin James was also present at the event. Just one of those unfortunate events but I have since purchased many more guitars since then. :)