I love road trips so much that I just want to go everywhere!

Anyway I would like to start planning a road trip that would begin in June and maybe end the first week of September. I am starting from Indianapolis, Indiana and heading to Key West first and then back up the coast through Maine and then into Canada.

I am wondering if I have enough time to do all of this in 3 months? My 12 year old son is coming with me.

My main concern is that I don't want to rush. I had a road trip from here to Phoenix and back during the month of November with my mother and it wasn't much fun. I found out that my Mother and I are not great traveling companions. I guess that is an important consideration when traveling with someone else to to make sure you travel well together.

Is there anything I should know about driving my own car into Canada?

Any tips? Suggestions?