Working brakes are more important than you think...
First tour was in college. Overall plan was to cycle from Boston to tip of Cape Cod and take the ferry back. I was the leader in that I had organized this for half a dozen college friends.
I had a 10-speed that I had bought earlier as a teenager. The brakes didn't work well, but I could typically slow myself down some before putting down my feet to stop. All was well until ~10 miles in when Claire Saltenstall Bikeway went through a small park on a path. The route went down a small hill and then around a bend. I went down the hill fine, but going too fast, rode off the side on the curve. My bike stopped. I didn't. I went flying over the handlebars and somersaulted to land flat on my bike. My backpack took the brunt of the impact as I landed mostly flat on my back. However a sharp rock had stuck into my lower right side and created a pretty big gash.
A sensible mature thing to do would have been to turn back, have my wound taken care of and scratch the trip. However, I was 19, male and invincible. Besides, I was the leader. So my friends and I found a pharmacy and were able to buy some large bandages and tape up the wound. That worked fairly well, though by afternoon as we neared the bridges to Cape Cod, it was warm and I was sweating some into the wound. That was painful. I was also fairly tired. A stop, eating a banana and sight of the bridges together pepped me up. That evening we looked for a spot to camp and came by a church in Barnstable, struck up a conversation and they were willing to have us camp on the lawn as long as we were out before services the next morning. We didn't pitch tents because it was going to be dry. It was painful as my friends changed dressing on my wound.
Next morning we got up early and cycled the remainder to reach P-town. We had some time to spare and wander briefly through town. After that boarding the ferry and a relaxing ride back to Boston. It was Sunday afternoon and traffic was light. Felt like conquering heroes cycling back through middle of town - and having accomplished the trip. Glad I went through with it overall.
However, advice (and if I'd listened) to have working brakes would have made for a more pleasant trip...