What time should I depart Montepulciano to catch 11:50 am FCO flight to US

Depending on your route and if current roadworks is still underway it would take at least 2-3 hours to drive it. Your are recommended to be there 3 hours before the flight...and if last summer was any indication, 4 hours prior would be better. Then however much time to get the car returned and to the actual airport. So cautious guess is depart 9 hours prior. It may sound excessive, but it gives wiggle room for when life gets in the way.
If asked, I would suggest driving to airport area the night before.

The recommendation to arrive in Rome the day before is one I would follow. There are simply too many details that could interfere with your timely arrival at the airport otherwise. A night in Rome is a small price to. I am already thinking of some great places to go for dinner.

Wise advice above! Professional transfer services estimate the drive at 2.5 hours BUT those are experienced drivers who've made the trip many times where you have not. That's also not taking into account any potential roadwork, heavy traffic or even accidents that could cause delays. Add the time to get the car turned in and to get to your terminal the recommended 3 hours before an intercontinental flight ...

It's a lot less risky and stressful just to stay in Rome the night before. My guess is that a much shorter trip to the airport will also make the trip home feel just a little less lengthy?

What time should I depart Montepulciano to catch 11:50 am FCO flight
to US

You should depart Montepulciano the evening before your flight and stay in Rome.
Anything else would be extremely risky. You'd have to leave Montepulciano in the middle of the night to arrive at FCO at least 4 hours preflight (1 hour to find car rental and drop car and get to terminal, 3 hours flight) - so you are not getting a night at your Montepulciano lodging anyway.

You might consider dropping your car in Chiusi the day before and taking train from there to Rome for your last night.

Besides, security, you will also have to go through exit immigration.

And as August is a popular travel month for Europeans, heed the three hour advice.

Stay near Rome the night before.

The day before.

Sleep at the Rome Airport Hilton or any other hotel you want, but be in Rome the night before your flight.

It took me almost 7 hours to drive from Arezzo to Fiumicino last summer. Due to a fatal accident on the A1 near Orvieto I was stuck on the freeway for hours under 100F sun. S..t happens. Fortunately my flight was the next day.

No later than 430AM ( which means getting up around 330)

hey hey js
spend the night in rome or at FCO airport.
drive daytime, return car, check in times are usually after 3pm, have dinner and relax.
no stressing out at 3:30am to start your drive to rome, as joe says. not knowing rome or italy roads, why would you put yourself in that position.
aloha

We just booked the Hilton Garden Inn by the Rome airport. There is a regular Hilton in the airport, but it's almost $300 nite the last time I checked, and wanted to charge resort fees. The Garden Inn has a 24 hour shuttle and is under $200 nite, at least for our May date.
Safe travels!

WOW! I never received as huge a response to a post as with this one!
I definitely am feeling we are a community.💕
Thank you so much for your heartfelt replies🙏🏻

JS

Jumping in, you got the best advice anyone could give. Would not even attempt to try and make the drive day of an International Flight. Spend the night, and save yourself a lot of headaches and worry. Not worth it.