Know the route for the first two days.
Have a functioning bike, especially one that has forks.
Don’t expect Bianchi to warranty your bent forks within a month of needing them.
Don’t have a cold.
Have read all the guidebooks and bike books that you plan to photocopy.
Leave enough time so that your laundry actually dries before you pack it.
Don’t have 75% of your summer class assignments still due.
Don’t wait until the day before you leave to request an extension for the assignments.
Don’t make plans to go to a vegan restaurant, no matter how good it is, the night before you leave (cause you probably haven’t even started packing).
Know someone with a car who can take you to the 100 places you need to go to the day before you leave.
Don’t get a flat on the bike you borrowed and be stuck.
Don’t forget where you hid the key for your bike lock and end up having to cut the lock with bolt cutters.
Try to make it to the bike shop before it closes so you can actually buy the parts you need before you leave.
It’s unfortunate that we did everyone of these wrong. But really, how else would we do it?