Tuscany
 

I am planning a last minute trip to Italy in mid May. There are four adults and we will be flying into FLR from the east coast. My original plan was to rent a car upon arrival and travel to an Agriturismo in the area of Siena. Thoughts were to stay there for five nights then return to Florence for three nights.Towns that we had thought might be fun day trips are: Pienza, Montepulciano, etc.
Found a great Agriturismo outside of San Gimignano.
The other couple would like to go to Cique Terra. I realize weather is always a factor.
Please advise me as to whether this would be too much travel in a short time or can we make it work without too much hassle.
Many Thanks!!

Well, let's get the spelling of Cinque Terre correct for a start!

Things to think about:

Are you sure you want to do a possibly 1 hr or more drive to San Gimignano after overnight flight?

San Gimignano area is not a great base for visiting Pienza or Montepulciano (1.5 hrs) as day trips. Certainly doable. But you might consider Volterra or Monteriggioni, which are closer. Double check drive time from the exact location of your agriturismo.

When would you fit in the Cinque Terre? Instead of the 5 days San Gimignano/3 days Florence? If you are interested in the art museums and churches of Florence, I would not take from time in Florence.

I think your plan is very reasonable. My favorite area in Tuscany is the Val D'Orcia (Pienza, Montalcino, Montepulciano, San Quiricio d'Orcia)

Others can advise on car rental.
You might want to rent the car somewhere close to San Gimignano, like Poggibonsi, instead of driving all the way from Florence.

Cinque Terre is possible as a day trip from Florence if you leave early. If that's something you'd like to do, plan for 4 nights in Florence and 4 nights in your agriturismo.

We arrived in Florence and took the train to Cinque Terre the same day. You could take a couple of nights off of the Agriturismo in the area of Siena to do two nights there. Just relax the first night and hike and tour all the villages the next day. You might be able to get a car rental in Pisa. The train will stop there.

It's not clear to me how many days/nights you have, so I can't comment on whether adding the Cinque Terre is "too much travel."

When considering how long you can safely drive after landing, also consider the time and attention spent in the process of renting the car. You'll need an International Driver's Permit which is available same-day at AAA offices.

The drive between San Gimignano and Montepulciano would take closer to 2 hours each way, so if Montepulciano and Pienza are high on your list you should probably stay somewhere in that area. However, as mama_mia mentioned, there are other good day trip options from San Gimignano. In addition to her suggestions, I'd add most of Chianti(Castellina, Radda, Greve, etc.).

Beyond driving times, also add some time to find parking outside of towns, walk into the center and return to the car. Day trips are not simply a matter of driving from one town to another.

AFAIK, there is no car rental office in Poggibonsi, but there is a Hertz agency within walking distance of the Siena train station.

Thank you for your keen insight.

So..thinking that maybe we should head a little further south and stay four nights around Pienza. then on to CT, maybe staying either a night in the CT area or 4 nights in Florence.

Myself, I could skip CT this trip, but have others that this is high on their list.

Any other thoughts, please comment

If you add a town in the Cinque Terre, I don't think it makes sense NOT to stay a night.

It would take close to 4 hours to drive from the Pienza area to, say, Vernazza. Onward to the Florence airport to turn in the car would be another 2.5-3 hours. Time to turn in the car and then taxi or bus into the city, another hour.

But for me, in a somewhat short trip, this is a time-eating detour. You wouldn't actually be seeing the Cinque Terre, just one town for a few hours after you arrive and a couple hours the next morning.

I agree that staying near Pienza is a better plan.

This is a fantastic place to stay, located just 3km outside of Pienza and surrounded by the most beautiful countryside-

http://www.fontebertusi.it/en/

The owners are very helpful and the property is lovely. I've stayed there many times and will continue to return.

I almost always rent at the airport and then make the 1.5-2 hour drive to my base. There have been a few times when my flight arrived in the late afternoon and I stayed in Florence that night to avoid jet lag problems and drove south the next day. So, if your flight arrives late, you might consider staying in Florence your first few days and then head to the countryside.