Has anyone ever done this type of outing? I found found one company, just wondering if anyone had personal experience?
Never done this type of tour, but I've driven Vespas in Florence and surroundings since the age of 14. I have tens of thousands of miles of experience riding Vespas and motorcycles in Florence and Tuscany.
Unless you have a long experience riding motorcycles or motoscooters you should think twice before attempting to do it in Italy.
The tour company "Fun in Tuscany" does Vespa tours. Last summer I did their Chianti Wine Tour and it was wonderful!! The staff is super nice and helpful. I talked to people who did the Vespa tours and they loved it!
WEBSITE: http://www.funintuscany.com/
The bigger question is do you drive the Vespa or are you riding double. Some tours you ride double behind an experienced driver. If you are driving the Vespa by yourself them Robert's comments are accurate. Learning to ride a Vespa in Italy is not a recommend first time experience. Use the search function for some prior postings on this subject.
We did a Vespa tour out of Florence and loved it. They took us out of the city to their base and spent time being sure we were comfortable driving a Vespa. Although I thought I was ready, I realized I was much happier riding behind my husband. (He had had a motorcycle many years ago, but he was confidant to drive, turn, etc). I LOVED riding behind him, as i was able to take pictures and really enjoy the scenery in Chianti. We were always on back roads and saw very little traffic. It was a wonderful day of enjoying the quiet of the countryside, the beauty of the area, and experiencing another part of Italy. I highly recommend it! .
My husband and I also did a Vespa tour out of Florence and had a little different experience than Shay. The details said we would have instruction on how to drive as we do not ride motor bikes at home. The instructions included "here's the gas, here's the brake, have fun!" We were taken out in Tuscany and the roads were definitely less crowded than a city center, but they were still two lane highways and we were often passed by other vehicles. Everything turned out fine and we had a great time and it was a very memorable part of the trip. But probably not the safest thing we have ever done. This is probably a better adventure if you are more used to riding motorbikes at home.