We are a group of 7 (5 adults, 2 little children) and will be staying in Buonconvento for 6 days this May. This is our first time in Italy for most of us. Our plan is to take two day trips to Florence and see (perhaps) climb the Duomo, visit the L'Accademia Galleria and take a paper marbling workshop. I need to book the tickets/passes and am wondering about the timing of everything. I've heard it's best to book the early spots but getting out of the house, driving to Florence, parking, etc. will be quite the feat. I would appreciate your thoughts and recommendations on planning these two days. We're considering driving the first day and then once we get our "sea legs" taking the train on the second. Thank you.
Take the train. Leave the car at the Buonconvento station. There may be no-connection trains to Florence in May, but otherwise it's a simple connection in Siena. It's super simple. Don't be intimidated - Nothing could be easier. A car will just unnecessarily complicate your trip.
There is no reason to buy these tickets far in advance because it's a local/regional train. You can buy them at the station from the ticket window or a machine -or- you could download the Trenitalia app and buy them the night before. I doubt it's even possible to buy them this far in advance.
Train schedules will come out a couple of months before travel. Take a look at the schedule then. You may end up being somewhat limited for evening activities in Florence, but I honestly don't know how late the last train connecting to Buonconvento would be. Maybe you'll be lucky and see a late departure when the schedule is posted.
Tickets to the Accademia and Duomo are a different matter. Those get gobbled up in advance. Alternatively, you can take a tour (from the same people who gobble up tickets) booked much closer or even same day sometimes.
Taking the train will take a little more than 2 hours and a half, but I do not believe driving would be significantly faster; Google maps says 1 hour 40 minutes, in real life I would add half an hour, plus the time to find parking (for example, going to Villa costanza parking area and taking the tram, that could add another half an hour).
Taking the train would be much easier than driving, if not fast; but you should realize that Buonconvento is fairly distant from Florence and transportation in rural Tuscany, with its endless row of hills, is slow. If you manage, for example, to take your marbling workshop in Siena (I do not know if such a thing exists there) it would be much closer.
We drove into Florence from outside the city in the countryside last summer and I won’t do it again. My usual parking spots from visits in the past were full (by porta romana) by 8 am. We had to get there by 730 am to get the last spots . In the evening we couldn’t drive in because the parking was worse. Perhaps there are other garages that have more availability that others can comment on. If there is a train definitely would recommend that.
Thank you all for this excellent advice. I really appreciate it.