Took my three teenage kids and our foreign exchange student on a Segway tour of Chicago last week. It was AWESOME. We booked it through Bike and Roll Chicago and Vincent was our tour guide. He did an amazing job teaching us how to use the Segway. It is REALLY EASY!! You catch on REALLY FAST, so don't be afraid to do this. I was worried about our Japanese exchange student who has limited English. Even she had an easy time learning how to ride it. They give you plenty of instruction and you get to practice riding it on a side parking area. It truly is easy to do! Once we all finished training (maybe 20-30 mins), we were off to see the Chicago sights. We rode along the bike trail near the lake, to the shed aquarium, Soldier football field, stopped at the beach to stretch & have ice cream, Buckingham fountain....ALL the sights! MY ONLY ADVISE....IF you can, do this on a weekday afternoon & not the weekend. Weekends the lake front can be crowded and more difficult to get around. We did a 2pm tour on a Friday and it was PERFECT. If you live in Chicago, just take the train into the city. You meet at Grant Park which is easily walkable from Ogilvie or Union Station. It's a BLAST and it was the highlight of our exchange student's trip!!
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