Choosing Tuscan towns for day trip from Florence
 

My family and I are leaving for our first trip to Italy next month. We’ll be starting with 3 full days in Florence before heading to the Amalfi Coast and finishing in Rome. I’d like 2 days exploring Florence and one full day touring some of Tuscany. We won’t be renting a car and will be looking to book a private driver or tour for the day (our family is a group of 10). I’ve looked at so many offerings and I really don’t know how to choose which towns to visit. They all look beautiful and seem to offer similar attractions that I hope to see...beautiful scenery, medieval hill top villages with some small restaurants, cafes, shops with locally made goods, a quaint piazza with a centuries old church, a winery to tour and taste...if you only had one day to see the best of this region at a relaxed pace...what would you recommend? And if you have any specific suggestions for an awesome guide or company we should contact it would be much appreciated! :)

I do not think you will be doing anything at a relaxed pace with 2 days in Florence plus a day trip elsewhere. Siena is a easy day trip via bus and there are many guided tours to San G. There are also tours to Chianti and wineries.
if you did a private tour I would head to the Area around Pienza, Montepulciano and Montalcino, particularly if you like brunello.

I agree with mjs about timing, esp. if your days in Florence include Sunday or Monday when many of the main tourist sights could be closed. If you think you'll never, ever be back to Italy, I'd go to Siena and perhaps a small Chianti town before or after. Otherwise, I'd leave the idea of "touring Tuscany" for another trip when you have several days.

How many days do you have in Rome? Some people enjoy a day trip from Rome to Orvieto, a lovely hill town in Umbria easily reached by train from Rome. You might enjoy this as a break from the busy-ness of Rome.

For private tours in Tuscany, I and many here have had wonderful tours with Luca of hillsandroads.com.

If you want to see a small hilltown take a tour - for a nice big hilltown try Siena just an hour by bus from Florence.

Thanks for the suggestions! What I mean by a relaxed pace is I’d rather spend a full day enjoying one beautiful little town than a hurried day hitting as many as possible. We definitely hope to visit Italy again soon. This trip we’ll be in Florence, Almalfi Coast, and Rome. We’d like to visit again to see Venice, Lake Como, and more of Tuscany. We’ll have 5 full days in Rome (days with no traveling or relocating) and a day trip to Orvieto is definitely on the itinerary.

"I’d rather spend a full day enjoying one beautiful little town..."

Just so you know, Siena is not little. It even has rush-hour traffic twice a day.

If you really mean little, you could easily visit two in a day, esp. if you have a driver who knows the roads, where the parking is, etc.

Pisa or Lucca perhaps. Catch the local commute train in.

If I wanted to avoid the larger cities and towns of Tuscany, I would focus on Volterra and San Gimignano.
Neither one is quaint in the sense that you will be the only tourists there, though.

If a tour included a visit to a winery, I'd probably want that as a late lunch in the early afternoon hours when the heat is strongest.

IMO, the towns of Tuscany and the colors of the buildings look best in the morning - and after 3/4pm and later until sunset.
If you departed early from Florence, I'd do the walking around in any town first thing. And reserve "indoor activities" like museums, churches etc. for the midday hours.