Best Routing Sequence

I don't think there is a train to Bellagio. It goes up the east side of the lake. You can take train to Varenna and then the 20 minute ferry to Bellagio.
The trip looks great.

Forget the day trip to Lucca. It's on the way to the C/T.
Looks just fine.

Depending on which trains you choose, it is 4.5 to 5.5 hours from La Spezia to Varenna-Esino on Lake Como from which you can take the ferry to Bellagio. Spend a 3rd night in the Cinque Terre and skip a 1 night stay in Milan. Unless you meant that night in Milan to be your last night before a flight? I’d still put 3 nights in the Cinque Terre and cut Bellagio to 3.

I would also not sleep in both Florence and Siena. Instead of daytripping to Lucca, see it on your way to the CT and day trip to Siena from Florence. That frees up two nights. Add a night or two to Assisi or add one to Assisi and one to Florence.

Assuming you fly out of Milan:

• Orvieto, 2 (pick up car)

• Assisi, 3

• Florence, 6 (return car; day trips to a Siena and Bologna by train)

• Cinque Terre, 3 (EDIT: stop in Lucca on the way)

• Bellagio, 3

• Milan, 1

Call up Autoeurope for your car; get zero deductible collision. They still may not be using Hertz in Orvieto due to complaints. In Chiusi Hertz is closest to the station. Half hour by train. All closed Sunday.

Orvieto do not take the funicular up to town; bus or cab.

To the CT village take the train from Campo di Marte at 7:28am.

Note that 2 nights yield only a single full day.

I'd miss sleeping in Milan, and go on to Bellagio 5 nights, and just day trip to Milan
As others have said train via Varenna.

regards

Follow Up: I appreciate all the insights shared! We have travelled in Europe a few times but still have so much to learn!

Clarificaiton-we do not fly from Milan. From Lake Como area, we are going to Switzerland for a week and then a couple of nights in Germany before flying back to U.S. from Frankfurt.

@k2wilde--Since we are not going until May 2020, I haven't figured out all the details but it is helpful to know know that Milan to Bellagio requires train and ferry. It still seems very doable.

@David--We were planning the day trip to Lucca rather than on the way to CT so we would have more time in Lucca (especially for biking the wall which sounds like fun) and would not cut into our time in CT.

@Laurel--Had not considered going directly from La Spezia to Lake Como. Honestly out of a month long trip, Milan would be the easiest stop for us to delete and therefore we only allocated one night. Since we are not likely to return, we thought it might be worthwhile for a single night.--not with intentions to do any major sightseeing but just to stay in the central area, walk around, and observe the culture. As stated above, we do not fly out of Milan but travel on to Switzerland from Lake Como.
Question whether we need 3 nights in CT but always open to input We have been to CT briefly on a cruise ship day trip which obviously only brushed the surface. We will not do any serious hiking so thought that 2 nights might be enough to do a couple easy hikes, travel between other towns via train, and explore the villages. Can you explain more about why you suggest 3 nights in CT?
Florence/Siena works out well for maximizing our hotel point stays. Florence (5th night is free) and Sienna (reasonably priced point redemption). Have also read (maybe RS?) that overnighting in Siena is preferable to day trip.

Assisi--Again can you elaborate on your rationale for 3-4 nights in Assisi? Others have suggested it as a day trip so we actually thought 2 nights would be adequate. Stay longer to spend more time in Assisi or for seeing the surrounding area?

@rzolezzi--I will definitely check with Autoeurope and make notes about your other recommendations.

@Gerard--Never thought about doing Milan from Bellagio. Maybe due in part to the fact that we can stay free in Milan with hotel points but in Bellagio, it isn't really feasible to use hotel points.

Mary,
Now a night in Milan makes sense. I would still put that after Lake Como as there are great train options from Milan to Switzerland. We take the EC train that goes between Milan and Spiez nearly every year when we go to the Lauterbrunnen Valley.

The reason I say 3 nights in the Cinque Terre is three-fold: I dislike 2 night stays, it is an awkward place to go for such a short stay, and if you have bad weather one day at least you have a chance at a good weather day as well.

If you want to cycle the wall Lucca, maybe devote 2 nights there instead of stopping in Milan.

Laurel--Thank you!

I have a tendency to give too much information but this seems to be a case where I have made it harder for those helping me by not providing enough.

When we leave Italy, we are planning to go to Luzern for 3 nights and Wengen for 3 nights, then on to Bern. So--not sure if you would still suggest traveling from Milan to Luzern rather than Lake Como area to Luzern. Just asking because I really don't know! Another possible option would be to go to Lauterbrunnen first and then back to Luzern but then it might make more sense to stop in Zurich rather than Bern. I should add that we try to find a balance between large cities and small towns but the small towns are generally the places that capture our hearts.

Assisi deserves more than a day trip.
I am mot overly spiritual, and certainly not religious, but I found a sense of peace and serenity in the town, especially early in the morning and in the evening, when day trippers were not around.

The places where you'll want to be are the places day trippers and pilgrims and people who are staying longer in Assisi will want to be, as well, so your plan is a recipe for crowds.

Each time I plan a trip to Italy, my mind wants me to include Assisi, even though the itinerary does not make any sense in some cases.

Do yourself a favor and give Assisi more than one day of banker's hours. It's worth it.
I think you will thank yourself for not having to hurry through all the sites and losing the sense of peace in the process.