July Itinerary

Both have too many locations
You only have 8 nights
I would stick to no more than 3 main locations
Each location change eats up a half day or more.

Ok if you don’t feel like traveling forward on arrival day- just give Milan 1 night
Milan has the least amount to see. Get Last Supper tix for late in day on Day 1 if of interest
Head to CT early am on Day 2
Spend 2 nights

Then train to Florence, pit stop in Pisa, check your luggage at train station
Onwards to Florence 2 nights
Not much time for a day trip to Siena a as you will only have 1 full day in Florence

Then train to Rome 3 nights

Milan 1
CT 2
Florence 2
Rome 3

If you can skip MIlan then go straight CT
CT 2
Florence 3
Rome 3

If Lake Como can be substituted for CT I’d recommend going there on arrival, it is closer and easier than getting to CT

Naples and Amalfi are too far for day trip. Save for next trip.

Thanks for the input.

I was thinking it might be…” looks more like a been there but didn't actually see anything trip”

I don’t want that! I’ll tinker with it.

Hi MG,
You are flying home from Rome, correct? With eight nights skip sleeping in Milan. The easiest thing is to visit Florence, Siena and Rome. The Cinque Terre is the outlier so removing that is a good idea because it involves transfers which are never fun when hauling luggage.
On arrival day buy train tickets at the airport (Malpensa Aeroporto) to Florence (Firenze S.M. Novella station): https://www.trenitalia.com/en.html. At 12:37 there's a train with one connection taking 3h 30m. Sleep in Florence for four nights. Two months out buy tickets for the Uffizi Gallery to guarantee reservations.
On your third day in Florence take a direct bus to Siena that will drop you off outside the old town (1h 15m). Do not take the train that takes longer, if you do you’ll need to take a bus from the train station to Siena’s old town.
From Florence’s S.M. Novella station take a direct train to Rome’s Roma Termini station (1h 45m). I would purchase this ticket now. The longer you wait the more expensive it becomes and there’s a good chance the seats will sell out. If you have trouble with Trenitalia’s website, try: https://www.italotreno.it/en.
Let me know if you need help.

We do fly out of Rome.

Since we land in Milan midday, I figure we will need some recouping time. The following day, my daughter really wants to see some sites and fashion. I wasn’t sure we could do much the day we land. That’s why I figured we would stay 1.5 days in Milan.

Also, we want to see a coast, so I thought we could stay two nights is Veranazzo. Then two nights Florence, two nights Rome. It’s about 1.5 days in each spot. Hard trying to eliminate much more.

Night 1,2 Milan
3,4 Cinque
5,6 Florence
7,8 Rome

Have you been to Italy/Europe before?

Have you checked lodging availability for three people? July is peak season , so availability and price may influence your itinerary. You must have AC.
I like the Lake Como suggestion, but there may not be any lodging available at this late date.
Sorrento/Naples/ Amalfi is too much, do drop that option.
I agree , cut Milan back to one night, or zero nights.
Also, count by nights , not days.
Two locations are best for eight days. You will have heat and crowds , which eat away at the energy levels.
A mother-daughter's trip sounds delightful, tho, so glad you have the opportunity to share this time together, and kudos, for planning this.
Safe travels!

You might need to eliminate CT just because there could be no availability left

Rooms for 3 are very limited
You might need 2 rooms

I’d stick with a hotel
Not an apartment or airbnb
Not worth the trouble for only 2 nights

Go to booking.com and see what you can find
Use the filters

Rethink Milan
We’ve seen the Last Supper and spent 2 nights
No need to return
Milan has the least of interest
To us it was just a big busy noisy city with a few things to see
If I had only 8 nights I would not give any time to Milan ( unless you want and are able to get tix to Last Supper- doesn’t sound like you are)

In 2022, we went to Europe (primarily Italy) with our “children” who were 22 and 20 at the time. Generally, we were in most locations 3 nights. Our family loved it, but all of us agreed we would have preferred spending more time in fewer places.

I agree with the guidance on Milan. We spent one night there because like you, it was the best place to fly into. Based on our experience, spend one night in a hotel, check in, get some rest, a good dinner, and maybe as others have suggested Last Supper tickets and then head on the next day. We stayed near Milano Centrale.

Where to spend the remainder of your trip…? Because you depart from Rome, plan for several days there. On our first trip due to us needing accommodations for 5 while in Rome, we stayed in a Best Western on Via Ippocrate—1 room, 2 true queens and a pull out sofa, with air con. It fit our needs and our budget.

Regarding the other stops, I think the most important issue now is what is available. We live on the gulf coast and are accustomed to heat and humidity, but I would NOT travel in Italy in July without air con. Maybe see what is available in the other cities you are interested in and plan from there. FWIW, we do most of our hotel research via booking.com—to enter a review for an accommodation, you must have stayed there, so we have a little more confidence in the reviews. Depending on the situation we book directly with the hotel, but we have also used booking.com to reserve accommodations with good results.

Also, we want to see a coast, so I thought we could stay two nights is Veranazzo. Then two nights Florence, two nights Rome. It’s about 1.5 days in each spot. Hard trying to eliminate much more.
Night 1,2 Milan
3,4 Cinque
5,6 Florence
7,8 Rome

If you don't, you will wish you had.

You provide no clue where home is, so how well you hold up in the heat may significantly affect how much you can do in a day.

My $0.02

I love Milan, which is a big city with many interesting and important historical and contemporary attractions. However, it is difficult to get a good sense of the city in a day or two.

Have you thought about Santa Margherita Ligure instead of a Cinque Terre village? You might get a more Italian--or at least more European--experience, and depending on your schedule the train transfer time from Milan and then onward to Florence could be shorter, though accommodations will still be tough to find at this stage.

You might also choose either Siena or Florence.

Do you have a list of things you want to see in each location? That will help you determine how long to spend.

I have been to Italy once many years ago, but not the kids.

Coming from the US, Do y’all think it’s possible to land at MLX at Noon, bus over to Milan and do the three hour crash tour that’s in Steve’s Italy book, eat dinner, then train down to Cinque to stay the first night? Or, I stay in Milan first night?

Sure
It is MXP then you take the Malpensa Express - a train to Milano Centrale
Check your luggage at train station and go tour
If flight is on time you might be in town by 2:30-3- no way to predict
It takes an hour to get to Milano Centrale from the airport (Malpensa)

Be back at Centrale in time to get your luggage - that could take time

No idea what time latest train to get you all the way to Vernazza
Use Trenitalia
https://www.trenitalia.com/content/tcom/en.html

Or really easier to stay overnight near the train station- you can drop your bags there on arrival
Then get up early and take train in the am
Remember you will be jet lagged

There are many forum favorite. Milan hotels near the station
A forum search will bring them up

We come from Texas, so we are accustomed to the heat.

I think we will eliminate the night in Milan. I have a hotel booked already in case we change our minds.

We will head to a coastal town , then Florence and Rome.

I sure appreciate all the input!

If you are going to Vernazza- make sure you have lodging!

We loved Santa Margherita Ligure. Not as crowded as CT, nor as touristy. You can visit the CT towns from there if you wanted to.

The 2 last trains I see now from Milan to Vernazza require 1 change in Sestri Levante- takes 3 hr 18 min.
Leave Milano Centrale at 6:05 pm, arrive Vernazza at 9:23 pm
Or
Leave Milano Centrale at 7:05 PM, arrive Vernazza 10:23 pm

That's a random day in July- looks like the July schedule is up for your route.

It is an IC train- which is a fast type train that makes some stops. You will have reserved seating.

Make sure your lodging in Vernazza will be there to check you in if you arrive late.

I went ahead and found lodging for Vernazza the day we land and for Milan (just in case). I thought maybe we can see what we want for a half day ( we land at noon), then take a late train to Vernazza .

According to the train schedule, I saw a 9pm departure on July 9th. Does that seem right?

That 9 pm train arrives Vernazza at 12:29 am
Make sure your hotel or lodging has a 24 hour desk to check you in!

Keep in mind this first day you will be jet lagged
You will have had no rest at all
Very few are able to sleep on overnight flights

I would want to be in bed by 9 pm

I understand wanting to sleep in Vernazza but there are direct trains from Milano Centrale to Monterosso meaning no changes and takes less time. Train travel after a night of no sleep will make you doze off so set your alarms.

What about staying in Levanto? Is that easy to train into? Would it be nice to stay in that town and maybe go hike monterosso to Vernazza?

Are rooms available in Monterosso? Hiking will take half a day and isn’t easy. However, the hike from Monterosso to Vernazza looks easier than from Vernazza to Monterosso.
There are direct trains from Milano Centrale to Levanto (3h). The train from Levanto to Monterosso is direct and takes 10-minutes.

What about staying in Levanto? Is that easy to train into? Would it be
nice to stay in that town and maybe go hike monterosso to Vernazza?

Levanto is a popular choice when the CT accommodations are full and/or the budget won't accommodate them. There's nothing difficult about taking rail there (explore your options on the Trenitalia site) and there are trains from Milano Centrale with no changes. It's also just a few minutes by train from Levanto to Monterosso. Still, I'd heed the caution not to take a late train from Milan the same day you arrive; you will be toast!

If you keep the late-train-to-Vernazza plan then you do need to make sure your accommodation can check you in very late at night (reference the check-in hours for hotels in Levanto too). Especially in the CT, hotels as you'd think of them are few, and many do not have 24/7 desk services. As well, some involve steep climbs or many steps to access and you don't want to be trying to find them in the dark.

Vernazza tends to be THE most overrun of the 5 villages.

Hiking Monterosso> Vernazza or the other way around:
https://community.ricksteves.com/travel-forum/italy/which-hiking-route-would-you-suggest-monterosso-to-vernazza-or-vernazza-to-monterosso
You'd need to purchase a park pass for this hike, and the trail is likely to be busy. Closed-toe shoes are required.
https://www.parconazionale5terre.it/Ecinque-terre-card.php

I have reserved places to stay in Milan and Vernazza and will decide later. I verified that we can check in after midnight in Vernazza.