The difficulty for any teacher is knowing when to let the student work out the problem alone, and when to step in with further instruction. What we did was very basic. At first you walk up and down the block, then around the block. You cross narrow, quiet streets, and then busier streets with traffic lights. You work on short routes the student wants to accomplish, then longer trips.
Some lessons are just for practice, but later they are more and more to meet the student's needs.
You work indoors, outdoors, and take buses. After a while, you don't have to repeat lessons for practice. Just be sure that the instructions are understood, and send them on their way. It gave us students a true sense of accomplishment to be able to manage that trip and what it had to offer. Congratulations, and goodbye.