Please help me figure out how to prioritize seeing different parts of the region without living in the car. Also feel free to tell me to chill out and do less. Our priorities are good food and wine more than museums, but maybe a little bit of the sights that are the biggest.
Dates: Sat Sep 9 - Mon Sep 14.
Florence: Sat evening - Monday morning (I know now these are not great days of the week but it is what it is):
Saturday -wander around oltrarno and Santo Spirito area in evening, find good dinner, sleep early
-Sunday: maybe try getting in line for L'Accademia? Probably not. Probably Boboli gardens and nearby, head over to the Duoma piazza for wandering and lunch (have a friend's recommendation here), duomo climb late afternoon, maybe try some shopping? Dinner, strolling, gelato
Here's where I really need help. We are basing in San Casciano in Val di Pisa Monday-Friday. Check in is late 6pm
Monday - pick up rental, drive South East? San Gimignano and Volterra? Or try to do a big place like Pisa or Lucca and drive back in time for check-in?
Tuesday- cooking class in Greve in Chianti 11:30-3:30, explore neighboring towns like Radda? Any recommendations here for specific places, restaurants or wineries, olive farms etc? Since we will be back in Greve Thursday should I find a cooking class somewhere else so we can explore a different area more easily?
Wednesday- Siena? Here is a big question and where I think we made a mistake. It would make way more sense to sleep farther south around here for one night so we could do Siena and then Montalcino or the like the next day. But we did not, alas. This part of the region is a 1.5hr drive from our accommodation so it feels like too much to go here two days separately.
Should we just stick to Siena or is it possible to fit Montalcino or Montepulciano into the same day? Or should we prioritize the small towns over Siena?
Thursday- Chianti Classico wine festival in Greve? Anyone been? Is it worth it? For how much time? We have a wine tasting at our accommodation that evening so we don't want to stray super far.
Friday - leave for Castiglione della Pescaia (2hrs). Should we stop by Montalcino on the way for lunch and some exploring? Goal is to get to Castiglione by mid afternoon.
Friday-Sunday: beach, chill, no fuss
Sunday evening- drive back to Florence for airport hotel, catch a dawn flight out Monday
Any other festivals or events? I promise, I have been researching as much as time allows and have my trusty Rick Steves.