Solo Train "Tour" from Rome to Paris

Personally (which is the only way I can answer your questions because you don't share anything about yourself and what you're interested in), I would want to spend more than a day in Florence.

Is there a reason for spending 2 nights in Paris, considering that you will have just been there in September? Could you get a flight from Paris to Rome on Day 1? Or even Day 2?

What about something like this?

Day 1 Arrive in Paris at 9am, depart for Rome noonish, arrive Rome afternoon.
Day 2 Rome
Days 3 Rome
Day 4 Rome
Day 5 Rome
Day 6 Rome to Florence
Days 7 Florence
Day 8 Florence to Milan (arrive in 10am)
Day 9 Milan to Tirano by train, Tirano to Chur via Bernina Express (Arrive around 4:30 and spend night in Chur)
Day 10 Chur to Zurich to Paris (arrive around 2pm)
Day 11 Paris to Home (10am)

If your flight from Paris to Rome is already booked and can't be changed, consider dropping Milan so you can spend an extra day in Florence.

Thank you for the response. That seems like a good itinerary. I am REALLY into art history. I don't really have much interest in going to Milan other than to visit the Last Supper but it's not something I HAVE to do. I wanted to skip Milan all together but the train to Tirano ( the beginning of the Bernina Express) only leaves out of Milan. I have been researching the Bernina Express and a lot of people think that the regular trains are better so I may do that so I can spend more time in Florence and skip Milan.

I will be going at the end of November which can be a bit rainy so I'm also trying to decide if I should go through all the trouble and possibly not experience the views.

Why not fly back from Zürich? Saves an extra night at the end which you could spend at one of you other stops. For example Florence for which you have only ½day (afternoon of day 7) in your current plan.

I quite enjoyed riding the Bernina Express route via regular trains on an overcast day in late September or early October. It was certainly not the best nor the worst day, weather-wise. But your plan really places all mountain-viewing bets on that single travel day, with no backup plan. It's a fair investment of time (15 train hours?) and money that may not pay off. On the other hand, flying from Rome or Florence to Paris is cheap (use CDG or Orly airport, not Beauvais), and more time in Paris is pretty much guaranteed to please.

I too would fly straight to Rome on your arrival day.
Rather than risk disappointment with the weather in November on the Bernina Express, I would suggest travelling via Luzern. Two nights here gives you the option for one of the nearby mountain peaks if the weather is favourable. If not, Luzern itself has other 'ground based' attractions.

Day 1 Arrive in Paris at 9am, then afternoon flight to Rome.
Day 2 Rome
Day 3 Rome
Day 4 Rome to Florence
Day 5 Florence
Day 6 Florence to Milan
Day 7 Milan
Day 8 Milan to Luzern (3hr 55min)
Day 9 Luzern
Day 10 Luzern to Paris via Basel (4hr 43min)
Day 11 Paris to Home (10am)

If you are "REALLY into art history", then I don't understand only one full day in Florence. I even prefer Florence to Rome (I studied Art History in college). I'd take one day from Rome and give it to Florence. BUT, make sure you see Daphne and Apollo by Bernini at the Borghese Villa while in Rome.

If you are really into art history, note that Milano has several great museums, as well as churches with important pieces.

Thank you all for the feedback. I think I will Just do my original plan of splitting my time between Rome, Florence, and a bit of Paris. I will be back to Europe in January and could add extra days to take a train ride in the Alps.

Europe in September. Europe in November. Europe in January. What a lucky person !!! Extremely jealous.