I have been struggling with 2 nights in middle of our itinerary, and would love some feedback - I know no one but me can make the decision but I am so torn!
Itinerary as of now is:
First trip to Italy
Arrive Venice am- 2 nights
Train to Florence- 4 nights (This is over Sun/Mon so I feel I need to keep 4 days since so much closed on Mon)
Get rental car- to Tuscany area- 4 nights (Siena, Montepulciano, etc)
To Assisi- here is my problem!
I had planned 2 nights in Assisi then drive to Orvieto to drop car and take train to Rome for 5 nights.
After reading more about Orvieto and all the great recommendations here I wanted to add a night to Orvieto or at least try to see town/cathedral. Seemed to make sense since we would be right there to return car!
Bear with me please-
Trying to work around the car rental return hours (closed 1-3) and train schedule to Rome is a pain. We really do not like arriving in a new city after dark- so returning car at 4 then taking 5:30 train to Rome gets us there later than we would prefer- close to 7:30 (Sept so it is getting dark by then)
There is a 3:23 train that we would not be able to catch even if we returned car at 3.
So basically I would like to be on that 3:23 train to Rome.
Should we-
Stay just 1 night in Assisi- arriving there before noon stay over and leave next day early afternoon to Orvieto. Gives us an evening and a morning in Assisi.
Drive to Orvieto- drop car about 4 then check in to Orvieto hotel for 1 night. See Orvieto that evening and next am- catch 3:23 train to Rome. Again- just an evening and morning in Orvieto.
I don’t care for the 1 night stays but can’t figure how to fit Orvieto in and still be on early train with car drop off hours limited.
Other option would be to leave Assisi really early on Day 2 get to Orvieto for a quick day visit then drop car by 4 and take the darn 5:30 train.
I hate to give up time in Assisi and I have already juggled days as much as I feel I can- I know people will say- save something for next trip- but even if we do go back to Italy (so many other countries we want to see!) I doubt we would go to Rome again so I want the 4 full days/5 nights there.
Should I just skip Orvieto completely? Just look at photos online of that beautiful cathedral? Or avoid it completely by returning car in Spoleto?
Should I cut time short in Assisi? Will I regret that?
Suck it up and arrive in Rome in the dark?
Sorry this is so long- but it has been keeping me up at night. I need to reserve our rental car and want this settled.