Ok so you decided you are going to conquer the world one city at a time. You are going to go everywhere and see everything and nothing is going to stop you.
We laugh in your face! You will not go everywhere. You will not see everything. Something (perhaps many things) will stop you. This is the reality of this kind of travel. This is why you need to come prepared.
Your first challenge is the limitation of your time. Since you aren’t staying in town long enough, you aren’t going to be able to do everything. Unless your destination is Charlottetown. Then you might be able to do everything. But beyond that there is just too much to do almost anywhere you are going to go. So you need to do your research and figure out what is most important to you and prioritize that.
Your second challenge, should you choose to travel in this crazy fashion, is your energy level. Driving all night to get somewhere is cheap and efficient but it is absolutely going to result in you feeling very tired at certain times in the day. Anticipate this and attack the exhaustion before it gets to you. Plan for an activity or form of transport in the middle of the day where you get to sit down. Don’t forget to eat and hydrate. Know your caffeinated beverage of choice and consumer it accordingly. Make a pact with your fellow travelers to not complain about being tired. Have a clear plan of what you want to do so that in moments of sleep deprived doubt and conflict you know where you are headed.
Your final challenge will be to know when to quit. There will be tons of awesome things around to see, but you must remember that you can’t see it all and that you are tired. Get out while you are still ahead and call it a day to remember. Know that you can always go back and see more another day.