We will be traveling to Florence in September and would love to take a Vespa tour of Tuscany. Has anyone used a specific company and would it be better to depart from the city or have them bus us to the countryside? Any advice would be great.
Don't have experience with that just yet but we did just book a Vespa tour of Tuscany in September with Tuscany Cycle (tuscanycycle.com) out of Florence. They bus you out of Florence and then do lessons before guiding everyone through Tuscany. There are a few companies who offer Vespa tours out of Florence but this company had the best reviews so you may want to check them out! Good luck!
Haven't done it myself, but I've only heard good things about Laura's suggestion, tuscanycycle.com.
You can also try checking with tuscanybyvespa.com, although I think they're a bit more expensive.