The guys at City Segway Tours are a) VERY nice and b) very fun. I have always wanted to do a Segway Tour and I could not wait to get on and get rolling when they agreed to let us join a tour.
First you watch a safety video (or in our case tweet and whrrl the entire time).
Then you get on and get comfortable doing it.
And then you get to go on probably the best sightseeing tour of Chicago....and definitely the most fun (bathroom break and hot dog breaks too).