Hello! I'm seeking itinerary advice for a 9-day trip to Italy, flying in and out of Rome, arriving early Wednesday morning, 9/18 and departing Friday morning, 9/27. It's my husband's first trip to Europe, my fourth time visiting Italy (long weekend in college in Venice-Florence and two work trips to Milan). My priorities are history/culture, wine + food, countryside, and having a good balance between maximizing our time in Italy without feeling rushed. My husband is happy with whatever I decide, but knowing him, he will most enjoy visiting smaller towns in Tuscany and having more leisure time. So far, I've booked three nights in Rome, two in Florence (train from Rome-Florence), then TBD for Monday, 9/23 - Thursday, 9/26. We will have to spend that Thursday night in Rome for our 8am flight the next day. I envisioned staying in an agriturismo Mon.-Wed. nights and making that home base, but I'm having a hard time deciding where would be the best place to serve as a base and how to get back to Rome on Thursday without having to drive/waste most of the day in transit. Since I've been to Florence before, I don't really want to make that our base for exploring. Should I consider staying in a town that's more serviceable to and from Rome (Siena, maybe?) Or should I change up the itinerary to include Umbria so we can train from Orvieto?

Thanks in advance for your help! Really excited about this trip and want it to be the best first European experience for my husband

Me, I'd choose the Umbria option, but it's one of my favorite parts of Italy.

If you're actually staying IN Rome that last Thursday night you're going to have to get up a 0'Dark-Thirty to make an 8 am flight, but I suppose you know that.

You could head on to Florence upon arrival in Rome so you don't have to do the last night in Rome and split the stay.
Maybe focus in on which Tuscan towns you'd be interested in to help flesh it out. Look at Lazio too--so many just focus on Rome but there are some places on my radar around Lake Boleno (and southern Tuscany is my absolute favorite). That way, you could keep the reservations you already have and end up somewhere close to the airport with the car for the last night.

You might want to consider what you'd like to see/do in Florence and then investigate the days and hours the sights on your list are open. In your current plan, you'd be arriving in Florence sometime on Saturday and departing on Monday which means your one full day is Sunday. Lots of the most popular sights in Florence are not open every Sunday.

Heading to Florence immediately on arrival in Italy is one solution to that potential problem. Pick up the car as you're leaving Florence, spend time in Tuscany or Umbria, and have your Rome time all at the end.

Or put Tuscany/Umbria between Rome and Florence. You could train to a town to pick up the car (multiple options) and on Thursday 9/26 take the train to FCO (via Termini) in the late afternoon or early evening.

But if you leave Tuscany/Umbria to last, I wouldn't necessarily choose the Tuscany/Umbria location based on travel time back to Rome. For example, after returning the car, the train from Spoleto to Rome takes about the same amount of time as the train from Chiusi to Rome. Orvieto isn't quite as convenient for car rentals as it used to be. No AutoEurope office there, and the only option I'm aware of is Hertz. We've had good luck with Hertz in Orvieto, but some here report problems they've had.

>>> arriving early Wednesday morning
>>> booked three nights in Rome,
>>> We will have to spend that Thursday night in Rome for our 8am flight the next day.
>>> If you're actually staying IN Rome that last Thursday night you're going to have to get up a 0'Dark-Thirty to make an 8 am flight, but I suppose you know that.

Your number of days available is not bad, so you are not that pressed for time. However, did you know you have
1. Thrown away about half day right off the bat while spending more money without gaining much in return?
2. Made the trip unnecessarily hectic at the end when you have sufficient margin to eliminate it?

By staying in Rome twice, you have added one full check-in/out cycle.
You are arriving early. What are you going to do until you can check-in in Rome? If you go to Florence straight upon arrival, you are more likely, not assured, that you can check-in upon arrival. You are using the otherwise waiting time to move to the next location. Also, I do not how you are thinking of getting to Rome arriving early Wednesday. If you take car of any kind, you are heading into the city during the weekday morning rush hour. If you take a train from FCO to Rome then immediately to Florence, you are completely immune from the road traffic jam.

As one poster mentioned, if you are flying home from FCO, and if it is flight to outside of the Schengen zone, you need to be at the airport at insamely early time and even earlier wake up time. This means you would probably need to go to bed early.

>>> how to get back to Rome on Thursday without having to drive/waste most of the day in transit.
If you arrive in Rome late afternoon or in the evening day before return, you are only in Rome just to check-in, sleep, and check-out.

Thank you all for the tips!! All very good points - I didn't even think about rush hour traffic getting into Rome (and I live in Austin, TX, I should know better). And checking into the hotel - I certainly don't want to wait with our bags when we'll be jet-lagged. I was also wondering about Florence on Saturday and Sunday. I checked the Duomo and Uffizi's hours, and we should be able to see one or the other on either day, but I'm not sure about other sites (nor have I put together a comprehensive list of what we'll do there, which sounds like my next step). The early flight on Friday is going to be rough, but I expected that. We connect through London, so not sure if that means we will have get there extra early.

Sounds like I need to flip the trip, start in Florence and work our way down through Tuscany or Umbria to Rome. I guess my next question is how hard is it to drive into Rome? Sounds intimidating. I was thinking we'd ditch the car somewhere along the way, but not finding many train stations in central and southern Tuscany.

>>> how hard is it to drive into Rome?
Hard, You are not allowed to drive into Rome during the restricted hours = the hours you probably want to drive. https://www.autoeurope.com/italy-ztl-zones/
Same for Florence, and many many other Italian cities.

Many drop the car in Orveito, but you can always just choose the airport. Determine the plan first, then you'll be able to find a drop-off point.

Book Rome-Florence tickets well in advance to snatch nice discounted fares - www.trenitalia.com and www.italotreno.com - two competing railways using same stations and tracks - take whatever is cheaper. www.seat61.com has all one needs in assistance booking own tickets from home - general info trains www.budgeteuropetravel.com; www.ricksteves.com.

If Tuscany, I'd drop the car in Chiusi. (AFAIK, the only company with offices in Orvieto is Hertz.) If Umbria, I'd drop the car in Spoleto or Foligno. If you'd rather drop the car a bit farther south, Orte is an option coming from both Tuscany and Umbria.

Yorkshire mentioned the airport. If you went to FCO, you could take the train to Roma Termini. If you went to Ciampino (smaller and closer to the city center), there is bus service to Termini. From either airport, you might choose to take a taxi or car service directly to your hotel. Taxi fares from the airports are set, but I don't know what they are currently.