Sounds like a great trip... I'm going to Lucca (among other places in Tuscany) in less than 2 weeks as well Unfortunately I never go to Tuscany in Autumn + I don't drink wine, so I won't be much help regarding your questions, hehe However, I have a sweet tooth and definitely recommend getting traditional Panforte bread (dried fruits and nuts) in Siena, in case you haven't tried it yet They sell them everywhere across Siena, but one of the most famous places is Nannini bakery (owned by the family of the famous Italian singer Gianna Nannini).I've enjoyed reading through this tread to get ideas for my upcoming trip to Tuscany the last two weeks of October! We are arriving in Rome and spending one night before renting a car and heading north. We would like to spend one night in a smaller town or Agriturismo before heading to Florence for 3 nights. I see there are a bunch of chestnut and other fall festivals around this time. Are there any you would recommend? Most festivals haven't posted their dates yet but I'm crossing my fingers for the Monte Amiata region for Oct. 21/22nd.
I would also love recommendations for wineries with lodging and other places to visit. We are going to Lucca, Siena, and Montepulciano but haven't made hotel reservations yet.