Before and after
Making a longer trip of it
The weekend is the fixed point. If you're flying all this way, it's worth staying on. Here's where we'd point you, and how long to give each place.
Worth the detour
Where to go from Florence
You've already paid for the expensive part of the journey. These are all reachable from Florence, most of them by train, and October is an excellent month for every one of them.
Hard-won advice
Three things worth knowing
Book trains a few weeks out
High-speed fares are cheapest well in advance and climb steeply near the date. Trenitalia and Italo run the same routes, so check both.
Base yourself, don't hop
Two or three nights per city beats one night in six places. Packing and unpacking will eat your holiday.
October is a gift
Warm days, cool evenings, a fraction of the summer crowds, and everything still open. Probably the best month to be in Italy. The first week is the warmest of it, which is not a coincidence.
You're already in the countryside
Most people base themselves in Florence and day-trip out. You'll be starting in the hills, forty minutes from the city, in a wine appellation with three serious producers within twenty minutes. Consider doing it the other way round.