HELP: 8 days Italy Trip from midwest in early September

Do the 8 days include your arrival and departure days? Edit. Or is it 10 total vacation days with 8 days in Italy

"what big city we should fly in and out from."

What is the home airport?

8 days are excluding the flights in and out.
We just bought tickets. Aug 29-sep 8
Minneapolis to Milan
Florence to Minneapolis
We are thinking to Milan to cinque Terre/Italian riviera
And from there to Tuscany and Tuscany to Florence to fly back.
Any suggestion on that route. We are flexible to places to travel during our stay.

If you have two little people with you, that's way too much moving about....just my opinion.
Each time you move towns, that takes up more than half a day.
If you look at a big paper map, not an electronic one, you will see how far apart things really are.
Perhaps pick two places to sleep, and spend four days in each.

We are splitting our trips in 2 main stays:
These places are yet to confirm and that’s where we need help.
Cinque terre/Italian Riveria
Tuscany
Others for easy fly in and fly out - to accommodate the 2 main stays. We are not really planning spend time in the hubs.
But I’m trying to suggestions on what places we should spend most time.

Looks like you have 9 nights- is that correct?
What time does flight arrive and what time do you depart Florence?
You will most likely want/need to be staying in Florence the night before your flight.

At this late date securing lodgings will be your biggest challenge.
CT might not have much availability.
I'd get on booking .com lickety split and see what you can find- either CT or Lake Como for starters.

Maybe 3 nights in that first location- (first day is travel/jet lag)
Then 3 nights in Tuscany town- perhaps Lucca?
Last 2 nights in Florence

Are you planning to rent a car or will you rely on train/bus?

Thank you so much for the tips.
We want to use trains for longer drives.
We can rent a car if it benefits us and if it is any easy.

It will be hot during your visit and the major tourist areas will be crowded. There may be limited availability for accommodations in the Cinque Terre, with travel in just over two weeks. I visited the CT on a Rick Steve’s tour five years ago. Based on photos and descriptions, it was the part of the tour I’d most looked forward to, but it ended up being my least favorite part. The tourist crowds were just crushing! Tuscany, on the other hand, offers wide open spaces, beautiful views, lovely villages. I recommend that you check out Agriturismo Cretaiole near Pienza. They normally require a one week Saturday to Saturday stay, so you’d be there 8/31 to 9/7. If they have availability, your family would love this place! The optional Dolce Vita stay will provide you with a bountiful array of food so you can fix your own breakfasts, snacks and even a couple dinners. Having a kitchen will allow you to have a relaxed evening in on some of your days instead of always eating in restaurants. On the tour of the family’s working farm, your kids will get to pet the animals, and later in the week your family will take part in a pasta making class on the farm followed by a traditional Tuscan dinner with all the other guests. You’ll never meet more warm and gracious hosts than the family who run this agriturismo! They’ll help you plan your week. For example, they’ll guide you to one of two hot springs areas where you can swim and relax, for free. Neither is well known to tourists but they’ll tell you how to get there and where to park. You’ll need a car if you are going to focus on Tuscany. You could start your trip with a night or two in the CT or do that after Tuscany, if you really want to see that area. I’d save Florence for another time.

I would not loose time going to the CT.
Portofino and Camogli are more authenticité, less crowed and more accessible. In Portofîno, there are also little islets nice to visit if you get a boat at the porticciolo. Take two days for this.
Tell me what you mean by Tuscany.
Tuscany is big. Florence is the capital of Tuscany and deserves at least 3 days.
In Tuscany, you have various smaller regions such as:
- The Chianti
-The Mugello
- The Casentino with Arezzo and Cortona . This region is famous for the Chianina beef of which the Bistecca alla fiorentina is made. The other famous Tuscan region known for its beef is:
-Thé Maremma. It also is very famous for its cowboys. It is really lovely and the nearby sea is authentic and uncrowded. You can also see loads of birds. If you go in this region, visit Tarquinia
- The Val d’Orcia
- The Senese Crete with the desert of Accona near Asciano
- The versilia ( Viareggio)
- there are also the wonderful towns of Siena, Lucca, San Gimignano. the Medici villas
-The wonderful region of Garfagnana (Castelnuovo di Garfagnana, Piazza Al Serchio)
- The Tuscan Archipelago with The isle of Elba and other islands which I love and do merit a visit
However with 8 days you do not have time to visit all Tuscany, so you have to choose what you want.
I live in Florence, so let me know should you want further details

With 2 young boys, consider if you want to spend your first night in Milan rather than a 4 + hour train ride to Chinque Terre/Rivera. Only you can decide this.

Monterosso is the largest of the villages in Cinque Terre, has a beach, and your best bet for lodging. It will still be very crowded.

As an alternative, look at Santa Margherita and Rapallo in the Rivera. These will be much quieter towns. From either town you have easy train access, about 40 minutes, to the Cinque Terre by train.

An easy location with the kids, in Tuscany, would be Lucca.
It has good train and bus access, and is an 1:17 by train to Florence.

If you want to visit central Tuscany, a car is the easiest with young children. You would need an IDP ( translation of your license) and know italys rules of the road.

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

Florence itself gives you many places to visit by both bus and train.

Edited to add.

Rather than stay in theCT, look at accommodation in Levanto. Has a great sandy beach and is an easy train ride to any of the CT towns. Having said that, With two young kids I would question the wisdom of going to the CT, only one town has a beach, all the towns have many steps, steep streets etc. to navigate, not to mention the crowds. Even in early Sept it will still be busy.

Thank you so much. Great suggestions. I love quite places and still want to keep it fun for little kids and us.
We haven't set our mind on CT or Tuscany region. Very open to where we want to go.
Its just we will fly in to Milan and fly out from Florence. Please keep your suggestions coming.

I'll join the crowd in suggesting you avoid Cinque Terre in early September. Since you're arriving in Milan, you could easily substitute lake time. Lake Maggiore & Lake Orta are beautiful, Orta will be the quieter of the two. Might be too sedate for little ones, since key activities are walking and eating. But Lake Orta has a great campground with cabins that has a nice beach on quiet, shallow waters and a playground. Could be fun. Or, you could head northeast to Lake Garda, which has a great water adventure park as well as beautiful towns, great food, all the Italian things you're probably looking for. Maybe visit Verona while at Lake Garda for a bit of (beautiful) city time.

For a second home base, absolutely go to Lucca. It is wonderful with and without kids, big enough to see things and have fun, without the big crowds to push through. I spent four nights there on a 2016 trip and loved it.

If you still want to go to the Italian Riviera instead of the lakes, look further west around Genoa. Take the kids to the biggest aquarium in Italy, then settle into a smaller Riviera town such as Santa Margherita Ligure.

These are just a couple of thoughts...there's much more but I think you would be wise to stay out of the big cities until the kids are older. Heat and crowds are no fun for littles (or bigs.)

hey hey bushrat
Look at lucca, within the walls. rent bikes with the kids, piazza with shops, cafes, restaurants. apartmentslucca.com see if something there you like.
Pinocchio’s home nearby in collodi and an amusement park for kids. Also garzoni gardens and butterfly house. take train up cinque terra to villages or further north. it is still busy season and may be crowded in places, you can only go so much with the kids. hope this gives you some options to look at. have a great time and sit at cafe people watch, kids can run around, relax you’re in Italy.
If you do decide to rent a car, look for parking availability, free or a fee, ZTL (do not enter) and get a IDP (coincides with drivers license) at AAA/CAA. Read up on it. all drivers need one.
aloha

Following your thread as we are planning the same time frame coming from Germany (originally from the MidWest as well! So your post caught my eye). I was thinking of training into Florence. Spend 2 days then branch out to Siena, Arezzo, maybe Pizza on the way up to Cinque Terre. But am wondering if I should revise that thought based on the tourist season comments here.

I'm not a museum person, but love wandering the towns, old churches/buildings, markets. I love to cook, and a more authentic personalized trip sounds wonderful. But, it's hard to know where to start at this late date. I would love to find a wonderful argriturismo type environment that is shorter than the whole week duration.

bushrat, did you settle on final plans for your family?