Florence to San Gimignono or Montepulcanio ? Itinerary Help Please!!

I'm not specifically familiar with the Heart of Tuscany Driving Tour, but it is not difficult to drive from Florence to various Tuscan hill towns and back in one day. Florence to San Gimignano to Montepulciano and back to Florence is about 270 km, so maybe 4-5 hours driving. Adding the time you spend visiting the towns, it's a long day, but certainly doable.

However, with just three nights in Florence, you'll only have two full days plus whatever portions of the arrival and departure days you'll have. There's a lot to see in Florence, so giving up a full day there will limit your time to get the full experience of Florence. That may or may not be okay with you; just take it into consideration when you decide what to do.

Staying in Siena or Montepulciano is a possibility as well, but again, you'll lose time in Florence if you do that. Personally, I liked Siena nearly as much as Florence, and Siena is closer to most of the popular Tuscan hill towns.

Think about it carefully. Personally, I wouldn't try to hard to see too much. You have a lot of wonderful places to see on your itinerary already, so enjoy them and don't press yourselves to see more.

And congratulations!

Anna Beth:

First, congratulations on your anniversary. My wife and I did a very similar trip to yours in June 2014. (BTW, we were married 40 years at that time and are now at 42). If you are adventurous, you might consider renting a car and driving from Florence to Rome. We did and loved it. We stopped at a friend's house near Lucca and then wound our way to Rome where we turned in the rent car. The drive is part of the experience. You can select which towns you want to see and how long to spend in each. I suggest that you turn in your car at a remote location (airport) and take a cab/bus to your destination. We did not. We selected an in-town location and experienced 5:00 traffic in Rome. I am from Houston and know the definition of traffic. The drivers in Rome have a very different view! The white lines in the street are merely suggestions and not lane markers. Fortunately, it all worked and worked well.

Regardless, enjoy!
Albert

I would say you have 3 options that make sense to me and should choose the one that best fits with your interests:

Option 1
Stay in Florence and don't plan any day trips since you really don't have enough time. Not just Florence but Venice and Rome are also rushed so wouldn't want to push myself. The 4 nights in Positano will be more relaxing for sure.

Option 2
Stay in Florence but book one of those all day Tuscany bus tours that typically can pickup and dropoff at your Florence hotel. Believe a very popular one goes to both Siena and San Gimignano plus a stop in Pisa but others exist as well and I am sure there is a more Wine orientated one that would take you to either Montepulciano/Montalcino or the Chianti area as well.
These seemed very rushed but will give you a quick taste of the towns and scenery along the way.

Option 3
Instead of booking in Florence book those 3 nights in either San Gimignano or Montepulciano and get a rental car for those 3
This would allow you to see the town you stay for 3 nights in very well and during the day you can explore the Tuscan hillside to your heart's content and get to see a couple of hill towns as well ; I would avoid Florence most likely in this case but could include Siena, San Gim and Montepulciano in your time plus nearby Pienza and Montalcino without much difficulty.