Impromptu stops

Between Milan and the Cinque Terre, there’s Levanto, Sestri Levante. Santa Margherita, Portofino and Porto Venere.
Between Florence and Venice, I vote for Padua (Padova).

Are you sure you want a car for all those locations?
Have you priced rentals?
Have you figured out where you will park it?

Between Florence & Venice, we like Verona. If you’re there during their opera season, you will want a reservation ahead of time. Other options are Padova or Ferrara. Check photos of Ravenna’s mosaics to see if you want to take more transportation time to see these stunning mosaics.

Between Milan & Cinque Terre, Parma has excellent food, and you could do a Parmesan, Prosciutto, etc. tour. Parma also has my favorite cathedral interior.

Since this is your first time in Italy, you definitely don’t need a car for Florence, Verona & Venice. The trains are very easy & fast. You could easily do the whole trip without one. Otherwise, be sure you understand the ZTL restrictions, so you don’t come home and find out you now owe several fines. I have traveled all over Italy down to Rome and always just traveled by train or the occasional bus.

The train website is trenitalia.com.
Venice is Venezia
Florence is Firenze
Milan is Milano

Thank you all for the suggestions. I am reseaching them all. We are fine with a car as we turn it in before Venice and we have booked before that based on parking to leave the car while exploring each previous area. Our idea for the two unplanned days is spontaneity, adventure and serendippity but I also want to know that that is possible or if I should just go ahead and plan a stop and book.

I think Padova might be worth a thought. The Scrovegni chapel is special (you MUST book in advance), the markets are fun, but not so much on Mondays as that day is quiet. The Orto Botanico is worth visiting, with five micro-climates in a spectacular greenhouse. Maybe you de-hire the car in Padova, and take a 30 minute train ride to Venice.

Or consider Verona. The Castel Vecchio is my favourite museum.

If you stay in a smaller city like Reggio Emiglia, you might check whether there is still a weekly "market day", and if it coincides with your visit. I'd mention Palladio's villas and the Villa Pisani towards Venice. How about Parma, Modena, Vicenza, Bologna. Despite it's being well-known on this board, I like Lucca a lot.

I personally don't travel without hotel reservations, and I avoid car rental when it isn't vital (for example, multiple days in Tuscany). Have you researched "Car rental annoyances in Italy"? You have too much chance of a second-rate place or a high walk-up rate. It's not 1952 anymore. (... when my parents took their postwar Babymoon with their belinio bambino.) And July is a high occupancy month. I'm inclined (at age 70) to consider air-conditioning essential in July, 2022, and not all places will have it. (I grew up in 1960's NYC without air conditioning ... )

You are all so helpful and I am going to have my husband read this as he is the one insisting on a car. Our first week is in Valiano, Sienna and Lake Como with our son in law driving. I would love to turn the car in but he is completely resisting. Thanks for the ammunition!

Agree with Verona in between Florence and Venice. We loved it!

I suspect most first time visitors to Italy think that traveling by car makes sense, then as they research and plan they realize that a car is mostly an expensive headache that often results in unpleasant surprises after you return home.
There are some areas where a car is best- Tuscany is one of them.

As I asked above- have you priced the car rental? They are super high this year. You will need a car that fits all of you and has room for all your luggage- hidden.
Renting a car strategically for JUST the days you really need usually makes the most sense. Trains are easy, fast and relatively inexpensive.

Be sure you all understand the pros/cons of driving in Italy. ZTLs are not the only issue. Parking and speeding tickets are as well. You won’t know you got that ticket til you get home. You will also get dinged by the rental agency- fees for providing your contact info to the police.

Assume all towns and cities have ZTLs, basically anywhere inside the walls.
If you stop somewhere en route, make sure all your belongings are well hidden before you park and take your valuables with you.

All drivers must have an IDP- International Drivers Permit- get at your local AAA
It is required by law, car rental agencies will ask for this, you may never need it but if you don’t have it the fines are substantial. Not having it may void your car rental insurance.

Have your husband (and any other drivers) read this info and familiarize themselves with Italian road signage:
https://www.ricksteves.com/travel-tips/transportation
http://driventoit.blogspot.com/2015/01/driving-in-italy-including-dreaded-ztls.html

We always use www.AutoEurope.com for our rentals - excellent customer service and usually best rates.

I completely agree with Tim about having hotels with AC booked in advance. I would never travel without reservations. My 91 yo mom is always amazed that we can't just go with the flow as they did for years in Europe and around the world.

I didn’t see anyone mention Ravenna as a stopover. It’s a bit of a pain to reach by train so if you do keep car from Florence to Venice might consider an overnight there to see the mosaics. Parking and access by car is probably a bit easier than Verona for example (which is a bit further away).

You'll need the car in Valiano (Sienna) since it is rural, but that's it! If your next stop is Venice, I would perhaps drive there for convenience, but if it is lake Como, definitely not. Trains between Florence and Milan are really faster, and the drive is a bore, plus you do not need or want a car around lake Como in July...

Actually, it wasn't my intent to give your husband a lecture about the freedom of the open road and how only losers and poor people ride public transportation. But Siena is an example of a car being an annoyance. My GPS kept trying to take me right through the center of the city (and ZTLs) to the huge peripheral parking lot I gave it as a destination. And where we finally gave up and parked (with waiting and searching) seemed like 150 feet or more below the main part of the city - endless steps.

You're not going to Sorrento, but every night we left our big hotel to walk downtown for dinner, we saw a line of 40 cars waiting to enter the underground parking garage. What a way to spend your vacation!

I haven't been to CT, but posters here say a car is worse than useless there.

We are convinced! No car for the two of us but the first week with our adult kids we will let them drive as we are mostly in Tuscany. Also, thank you all for the great suggestions of where to stop. I have lots of research to narrow it down but it seems there us a lot to choose from and we can't go wrong.