My favorite trips are two solo boats. I bet three would be OK too. Paddle when and where you want but still have a bit of company. Works for me.

One thing my partner and I agreed on was never to portage into a new lake until we re-established contact. In other words we both went across the portages together. This proved to be wise when some mis-comunication would of put us on different lakes. Fortunately we had an iron clad agreement so we knew that somewhere on whatever lake we were on the other was also there. No guessing.

When you plan your trip in the fall don't forget it gets dark early. Fortunately there shouldn't be much bugs which makes for some good times around the fire to help pass the evening (hence axe and saw ;) )