Initial itinerary help

It's hard to know how to advise about your length of stay in Rome since there is certainly enough there for much longer than five nights. One factor might be whether you want to see the Vatican Museums, which are large and potentially time-consuming, and/or the Borghese Gallery. The latter is a 2-hour experience, but I believe you need to be there a good bit early, so figure on about 3 hours all told. If neither of those is on your list, 4 nights might be OK since a lot of Rome's other sites (though plentiful) are quicker to visit if you can manage to avoid the lines.

You might sort of finesse the issue by planning to pick up the car in Orvieto late on Day 5 (after your fourth night in Rome) or early on Day 6 if you can get a good rental rate there. I believe Hertz has an office in Orvieto; not sure about other options. Orvieto's only about 90 minutes by regional train and there's no price penalty for buying the ticket on the day you travel on a regional train.

If there's still lots you still want to do in Rome that day, you can spend much of Day 5 in the city before heading to Orvieto. If you're ready for a change of scene, you can head up to Orvieto rather early. It's a very pretty hill town with actual sights to see, including a fine cathedral and a nice museum. There are good restaurants, and it's a very nice town for strolling around. Much of the historic district is pedestrianized. So Day 5 would be sort of "Rome or Orvieto". If you've managed to see enough of Orvieto on Day 5, you get an early start the next day and have a shorter drive than if you had spent five nights in Rome. Just a thought.

I'd be inclined to skip Venice on this trip and spend my time between Rome and Milan, with the Cinque Terre or Varenna included if the final itinerary has some slack. Maybe re-visit Venice on your third trip and add on some new destinations in northern Italy (Padua, the Dolomites, etc.)

Thank you so much! I am still struggling a bit with this but am inclined to agree that I should consider leaving off Venice and Varenna this trip. Wish I had more time!

A couple more questions if you do not mind: If do decide to take the train to Orvieto to get the car rental, do we miss much, if any, scenery on the drive vs. the train?

Does it sound like a good plan to possibly get up early, drive to Orvietto and explore, drive to Siena later in the day, stay Siena; next day explore Siena and stay another night there; see San Gimignano on way to Florence? Was just trying to minimize the "moving hotel days." Also, I guess, could just consider seeing Siena from Florence for a day trip? Definitely going to the Cinque Terre.

Thanks again.

I have never driven in Europe so am not the best person to address your most recent questions. The plan sounds reasonable to me, though.

I also can't comment on the scenic virtues of the train trip vs. the drive to Orvieto. Rome2Rio.com suggests that the rail line and highway are close together for most of the trip, and the transit times are similar. I think it might take less time to pick up a car in Orvieto (folks say that's not as quick a process in Italy as it is in the US), and you wouldn't have to drive out of Rome, dodging the areas you're not permitted to drive through. You also wouldn't have to worry about where to park the car in Orvieto. But it may well be that rental rates would be higher in Orvieto, and if you need an automatic transmission, I'd be more confident renting in Rome.

Couple of thoughts:
Pienza is a good place to stay a couple of nights to see Scenic countryside on your ride from Rome to Florence.
Nearby Montepulciano and Montalcino also good options.

The day you move from Pienza hotel to Florence is ideal time to visit Siena, Siena is easy to drive and park in route and well worth seeing. I would choose Siena or San Gimingnano give the time you have.

Would give Cinque Terre 3 nights, especially after a long drive and it being a bit of a hassle to get there, often with stairs to where you are staying and then get to your next destination that 2 nights feels like a lot of work for the time. 3 nights feels much better.
You have 15 nights ; if you did 5 Rome, 3 Pienza while you have the car, 3 Florence including a day trip by train to Lucca one day, 3 in the Cinque Terre that is 14 , stay the last night in Milan see the Duomo and not make your last morning too crazy.
This is a proper amount of time for each stop I feel.
I think you could squeeze in Lake Como in for 2 nights if you dropped Rome to 4 nights but would also have to leave very early the 21st. May want to pay for a car service rather than rely on train.
Don't see Venice working out well with your need to fly out of Milan, if you could fly out of Venice it could for 2 nights instead of Lake Como.

Umbria's countryside is as lovely as that of Tuscany. I am a slow traveler and was quite happy to spend 2 full days in Orvieto. If you can get a good deal on a car rental from there, it may be better to take the train from Rome. Do spend a night or two in Assisi as well, you won't regret it. It's not served by the fast trains, so getting there without a car can be time-consuming, so you might as well take advantage of being fairly close with a car and seeing it.

If you want to include both the CT and Venice/Varenna, you will spend more time traveling. If you eliminate Venice, it's pretty convenient to get to Milan from the CT by train, and there are sigts enough in Milan to fill a full day or even two.

Thank you so much. I will keep working on this and certainly will probably have more questions. Appreciate all the help very much.

If you decide to pick up the car after Rome, I think Orvieto makes sense, but what we did was book an agency on the ring road of Rome through AutoEurope. We took a taxi from our hotel to the rental place, checked out the car and got right on the Autostrada, easy!

I love Lucca and Venice, so I'd probably skip the CT since it's a bit remote and work Venice in before Milan. If I remember right it's about 2.5 hours by train from Venice to Milan, stay your last night in Milan.