Alternative to Florence for one night
 

We're spending a total of 21 days in Italy and have four nights booked in Florence in October. We are considering reducing that to three nights and substituting the fourth night for one night in a town outside of Florence. While in Florence we have already booked a one day tour to SG and Sienna and Chianti region. This can be cancelled if necessary. What would you suggest as a one night destination outside of Florence? Would we access by train, bus or car rental? Or do we just stay put in Florence?

Where else are you already planning on going, besides Florence, in your 21 days total?

Rome, Naples, Calabria and Sicily.
Flying from Palermo to Florence.

No interest in Venice? That can be done as a "day trip" from Florence.

Lucca?

Venice by train...or Bologna, or Milan....but where are you going after this "1 day" jaunt....do you have to get somewhere for your flight home, or what?

Would you do this one night after you land at Florence or the night before you fly out of Florence? If the last night, you have to figure out the logistics of getting to the airport at the hour you need to be there.

All of these are easy and close by train from Florence:

Pisa
Lucca
Montecatini Terme
Arezzo
Bologna
Ferrara

But with only 4 nights/3 days in Florence, and one day booked out of the city, I'd probably keep the 4 nights.

Two days to see everything in Florence wouldn't be nearly enough time for me, and if your days there include Sunday and/or Monday, you may find some things you want to see aren't open.

I also really, really dislike one-night stays. I feel like I barely arrive and immediately start feeling pushed for time.

Unless there was some particular place that I was busting to see (which seems not in your case) my personal choice would be to stay in Florence that extra night rather than pack up and move on. I'd do a day trip with the extra day - probably by train - taking the full day and returning late after dinner if I felt like it.

btw a one day tour which includes Siena, San Gimignano and Chianti region makes my head spin. It would definitely just be a tiny taste of each. An alternative might be to take an early bus from Florence to Siena, then a bus to San Gimignano in the late afternoon then bus or taxi to Poggibonsi for train back to Florence. Still too rushed for my taste - I would choose one or the other - but better in my view than the tour which includes three different locations. Or choose a tour which is less ambitious. Bus timetables at http://www.tiemmespa.it/ Then a more leisurely Chianti tour on another day.

I'd just keep it in Florence. Unless you juggle things and can add a couple days in Venice.

I've been to Florence and it is an amazingly beautiful, historic & fantastically preserved city that is a real treat if you are fascinated by the Italian Renaissance.

But if you are not so interested in painting, sculpture, architecture, and are more interested in experiencing a different side of Italy -- a smaller town, a castle village, local markets, or just some variety -- then it makes sense ot spend a night someplace else if you are ok with changing hotels. Lots of good suggestions here about easy-to-reach alternatives. It depends on what you really want. If you would like to do something really unusual, check out going to Marradi for the chestnut festival in October. If you go there you can experience real Italian small town life. There are other chestnut festivals near Florence in October too.

Thank you all for your responses. We appreciate you taking the time! We are having a hard time limiting all the wonderful possibilities of things to see and do. We don't know if we will ever make it back to Italy and want to take in as much as we can. We will now look at a less adventuresome day trip so that we can truly enjoy our time and not feel rushed.
We have made adjustments to our 5 days in Sicily thanks to the experience of those on this forum!
Our 4 days in Florence are at the end of our trip before heading to Rome for one night and then our flight home. Will definitely check out the many alternatives suggested and might even try to take in a chestnut festival!