We are traveling to Italy in November. Wondering whether we should drive from Rome to Florence and see a few towns along the way or, instead, take a day trip from Florence after we get there and see places like Montalcino, Pienza and Siena. We already have our hotels in Rome and Florence.

You didn't say how long you will be in Italy, which of course makes a big difference for your trip. I highly recommend staying 2 nights in Siena between R & F. It is a magical town!! You can spend the first day when you arrive seeing the sites, and then pick up a car rental on day 2 and drive down to Montalcino, Pienza & Montepulciano easily on day 2. Do book your rental before you leave as it is much more expensive if you rent in Italy. Wandering the small back roads were absolutely magical.
The best part of Siena is the night when the day-trippers leave and the Italians come out. You'll love El Campo and the Duomo.
Remember that Florence is large and Rome much larger, so Siena gives you a completely different experience. I returned to Florence for my 50th birthday, to find it as wonderful as ever 27 years later. You'll love it!

Thanks for your response. We will be in Italy 9 days. We already have all of our hotels and destinations. We are just trying to figure out whether it makes sense to drive from Florence to Rome and check out Tuscany or simply to take a day trip during one of the days we are staying in Florence.

I would definitely rent a car in Florence as we did once, and drive around Tuscany for a day. Driving in to Rome to return a car would be a nightmare. You'll be amazed at how much you can see in a day. Siena will certainly be one of the highlights of a day of wandering. Just follow the signs for the centro, park in a lot, grab some food and wander for a couple of hours.

Just do the daytrips from Florence after you arrive in Florence either by driving or by taking the train and/or bus. I also recommend visiting Siena.

Hi--
Just my 2 cents... just got in today from a 12-day trip to Positano and Tuscany....

I think it really depends on what you like/wish to achieve during your visit. At the recommendation of others, I planned on seeing Montepulciano, Montalcino and San Gimignano in a day, but loved Montepulciano so much and ended up spending much of the day there. Later we hit Sienna for 2 days (we day-tripped to Florence on one day), hung out for the Wednesday market in Sienna, and then circled back to my personal favorite, Montalcino for a night before heading back to Rome.

If you like running from town to town to check them off your list, then yes, you can do several cities in a day. However, if you want to take the activity in the piazzas, taste some wine, and stroll through the towns, then more than a day is needed (especially if part of that day will be spent driving to and from.)

In either case, all are a relatively short driving distance from Florence. (I think Montalcino is about 2.5-3 h from Rome)

Enjoy your trip... make sure to bring warm clothes.... it's gotten really chilly in the last 5 days!