3-Week Itinerary Advice

Looks like you have 18 nights?

I'd add a day to Venice, a day to Rome, and a day to Tuscany or Amalfi.

Maybe
Naples 1
Amalfi 3 or 4
Rome 3
Tuscany 4 or 5
CT 3
Venice 3

Remember: when you say "2 nights here, 2 nights there" what you actually get is one full day to spend in each place - one of those other "days" is consumed by travel.

The start of your plan looks fairly reasonable, until you get to Rome...

Rome certainly deserves more than one full day. (!!!)
CT doesn't need 3 full days.
What exactly is "Tuscany" (in your plan)? How do you plan to spend your time there?
CT is nice (nice and crowded). I think Americans who go to Europe for "beach time" make a huge mistake. Your days in Europe are precious. You can go to a beach somewhere closer to home, no? (not sure where you're from) Better beaches in places you may be able to get to quickly and easily.

So glad you were able to add another week!

But, even, so, this is a lot of time for most kids to be spending in trains (and train stations!), packing and unpacking, getting to and from your accommodations, and, in the height of tourist season, stuck in lines and tourist crowds. You are planning on going to the six most popular locations in Italy. And it will be very hot.

Imagine in as much detail as possible what this will actually be like. When we took our grandson and his baby sister to Italy in March, our first thought was to take the train from Rome to Brindisi in Puglia ---- "Oh, Isaac loves trains" --- but when we really imagined that journey we decided to fly instead. Later in that trip, the relatively short train ride from the Rome airport into a Rome train station convinced us that we were correct.

Of course, it depends on how old the kids are and what each one is like and what each one's interests are, but I would seriously consider picking three (maybe 4) places and spending more nights in each. Then they will experience more of the joys of Italy instead of traveling through Italy.

Also consider skipping Naples and the Amalfi Coast (driving a full-size van? Or two cars?), flying into Venice and out of Florence or Rome (what time would your flight leave Venice?), and staying in one villa or an agriturismo (maybe two in different areas) in Tuscany that has a pool. Tuscany has beaches, too.

The Italian Riviera is wonderful. The Cinque Terre is just one part of it - the one most tourists seem to focus on. Consider going north up to Santa Margherita Ligure or Camogli. It's very easy to get up and down the riviera by train between these towns and the Cinque Terre.

I think you are moving around too much, especially with a large group. What are you thinking with amalfi coast? We spent 10 nights on it two years ago. I will say the beaches are good for a day of relaxation but would not say they are a highlight. On the amalfi coast anyway they are rocky so bring water shoes and expect to pay to rent chairs unless you like to sit on pebbles for the day.

Since you are flying into Naples and out of Venice, I would eliminate cinque terre and add two to three days to Rome and one to either Tuscany or amalfi coast depending on what you want to do in those areas. I am not sure what you mean by amalfi coast. Many people stay in sorrento but it is not actually amalfi coast. Amalfi town I think is better to stay in than positano especially with children.

Moving around takes time and is harder with large group. We stayed five nights in Rome. Personally I think it is not worth the trouble for two nights. It is a big confusing city and I think you will like it much better if you spend more time there.

Beth

With the size of your group and, especially, with 4 children, I suggest you rent a large house with a pool, for a week, for the Tuscany portion of your trip. And be sure to have at least 2 or even 3 cars, rather than 1 large van. That would allow some of your party to take a breather while others pursue the sights that interest them and would reduce potential friction over decisions about where to go. The Tuscan Coast also has some nice beaches. As you are planning for high season, I would get cracking on finding accommodations.
See my advice about choosing lodging in my reply to “Tuscany and Umbria help Planning ,” posted on 10/31.

Thanks all for the input. I edited this to correct that we have THREE nights in Rome not two. The kids are 8-12. We planned to rent two economy cars, not one large van. In Tuscany, Florence is a must of course, also for three of us Pitigliano (which I realize is quite south but we have family there).

Economy cars are quite small
That would be 5 people PLUS luggage in each car
Be sure you travel light!

Be careful when choosing cars. The term, “economy,” is just above the “mini” class in Europe. I should think you will want 3 economy cars, or go up to the “compact” level.

I would not be that jazzed about a trip to CT in July. It is crowded (understatement of the century) and there is just one little rocky beach at Monterosso. You know Tuscany has a coast, right? It also has some of the best beaches I have seen in Italy, many in close proximity to Pitigliano. You snuck that one in there, but it is very significant to your trip planning. Where in Tuscany were you thinking about otherwise? Pitigliano is a wonderful option I hope you are considering. It gets its fair share of day trippers, but you are going to all the most popular places, and a respite might be nice.

For your Naples, Amalfi Coast portion, to select a village you need to indicate what day trips you are interested in, such as Pompeii. Minori and Maiaori have sandy beaches and though you won;t need a break starting off, the kids might enjoy kicking it there while some of the adults go on day trips.

Rogue,

Here's my take from personal experience.
Family trip, us, (grandparents), our 3 kids & their spouses, 4 grandchildren ages at the time 2/10 yr olds 2/14 yr olds. The time it takes to move this group is twice as long as moving as just a couple. I've also traveled with a group of 9 older adults. Complaints were different, but moving around from place to place presented some of the same problems.

Here's what I'd suggest.

1 N. Naples as you arrive so late in the evening.

The next day train to Salerno. Ferry to Maiori or Amalfi.
As noted above, Maiori has a good beach and ferrys to the other towns. It's easy to reach Pompeii by train from Salerno if that's on your list.

https://www.travelmar.it/downloads/orari_travelmar.pdf

3 N. AC.
Edit. This is where my daughter (who lives by Naples) and her friends stay.

https://www.simplebooking.it/ibe/hotelbooking/search?hid=3274&lang=EN&cur=USD&REFCODE=MOBILESITE#/q&guests=A,A&in=2018-11-23&out=2018-11-26&coupon=&REFCODE=MOBILESITE

Check booking.com using filters to narrow down your choices. For apartments and villas.

Return to Salerno for your trip to Rome.

4 N Rome.

Make sure you book for the Colosseum and Vatican Museums if their on your list.

Taxi to Rome Tiburtina station to pick up rental.
I use Europecar. You will have easy access to the A1 from here. If you've never driven in Italy, please read this and their PDF

https://www.italybeyondtheobvious.com/dont-mess-with-ztl-zones

Our g-kids enjoyed this park on the way to Tuscany. Pack a picnic, and let them stretch their legs. (About an hour from Rome)
https://www.italysbestrome.com/bomarzo-monster-park/

From Bomarzo head to an agriturismo, if this one is available, take it. It's stunning.

https://www.homeaway.com/vacation-rental/p6377683

4-5 nites Tuscany. Close by, (Acquapendente) very cute village, good market, wonderful cheeses, hams,
Wine and olive oil. They also have a blues festival in July and a art and food festival.

Things to do in the area.

https://saturniahotspring.com 1hr away. Everyone should enjoy it. Bring water shoes or flip flops. DON'T wear jewelry!! It turns black.
Another picnic spot, at least bring plenty of drinks.

Easy day trips. Pitiglino 30 min. Pienza, Montalcino and Montepulciano 1 hr. The whole of the Val d'Orcia less than 1hr. Radicofani, Vignoni, Castiglione d'Orcia. Could all be visited in a day.

Drive from here to Siena 1 1/2H or Castellina 1H 45m on your way to Florence. Drop car in Florence. Be aware of ZTLs.

2 N Florence. Should give you enough time to hit the highlights. Hotels are your friend here.

Afternoon train to Venice.

3 N Venice.

I really would avoid the CT. While they're some of the prettiest villages, they're also extremely crowded. For the time it would take to get there and the lack of things for the kids to do, I don't think it's a good fit with the rest of your itinerary.

If you have any questions, PM me.

.

Thank you all so much. We have dropped CT in favor of a few days at Lake Garda. This has been very helpful!