Gut check - flights

Obviously, we will need a car. I'm weighing the direct flight ease against arriving in Rome and travelling to Florence either by train and picking up a rental at SMN, or renting a car in Rome and driving after a red-eye.

Am I correct assuming your first stay is in Pienza and you want to reach that destination the first day? If so, I think your best bet would be to fly into FCO, rent a car there and gut it out to Pienza. That would be a three hour drive. An alternate would be to train to Orvieto and rent the car there. Then it would be an hour drive to Pienza.

We flew into FCO, arrived in the morning and drove our rental car to Greve. However, because of Skymiles, we were able to upgrade to first class and slept really well on the plane. How long to you plan to stay at each location?

@DougMac - Yes, our first stay is in Pienza and we want to be there on Day 1. How I wish I could fly first class but alas we will be cramped in the cheap seats. I don't sleep well on flights but fortunately my husband, who will be driving, sleeps easily anywhere.
We are in Pienza 7 nights, 2 nights in Florence, and 3 nights in CT. I forgot that I do have one night "on hold" at the end of the trip in case we decide to overnight somewhere close to the airport.

I must tell you that I bookmarked another post you wrote about driving from FCO to Greve. It was very helpful.

I would not drive three hours under those circumstances, but we’re all different in our risk assessments. We have done under two-hour very straight-shot drives on arrival, so I am realistic—but this drive might be windy and challenging toward the end, just when you begin to get weary. Could the one-night you have for wiggle room be added to the start of the trip?

My gut would tell me not to drive that distance after a red eye
Also not to try driving from CT to Rome on flight day

Do you really plan to sleep in CT the night before your flight out of Rome?

I have found google drive time estimates to be "optimistic", and it shows 5 hrs from CT to FCO. Adding time for a rest stop, and a pre-turn in gas stop and the 3hr international flight check in allowance you would need to leave CT about 11 hrs before your flight time. That is the 'no problems' scenario. If there is road construction or some other delay on the way...... well, you get the idea.

I'd say IF you must travel after your overnight flight TRAIN not car! I've twice driven after arrival - bad decision. Now if I must travel on arrival date it is a train. The train to and from FCO is easy.

I would NOT drive 3 hours after an international flight. Take the train/bus. That’s a 5+ hour voyage, so it may make more sense to fly to Florence, then take a bus from there.

Always fly the simplest routing because Murphy devotes a lot of energy to messing up air travel