Itinerary for Italy - please give sanity check

I would be tempted to skip Bologna altogether and add one night each to Venice, Sorrento and Rome.
If you are intent on Bologna, I would still remove one night and add it to Venice, where you only have one full day as it stands (arrival day is a jetlagged mess for most).

Also, I assume that skipping Florence is intentional?

I like the idea of adding a day to Venice. You're right on the jet-lagged arrival day. That's more or less a throwaway day.

Yes, Florence is intentionally off the list. I want to experience that in a future trip - and at my own pace (i.e. not with the family in tow),

. with the family in tow

Just what is the composition of family for this junket?

Agree with the thought to use the Bologna days for Rome and Venice

Are you guys recommending robbing from Bologna and giving to other cities because of what you know about Bologna (i.e. not worth seeing) or what you know about the other cities (i.e. need more time)?

Family = wife and kids aged 8, 20, and 24. None of these people have the patience for experiencing Florence at my pace.

what you know about the other cities (i.e. need more time)

Not been to Bologna, but know you could/would be well occupied with more time in Venice and Rome and reduce how much time is spent 'in transit' and moving in/out of hotels.

I like Bologna. It has a huge medieval district. Definitely worth visiting. But it's not Venice and it's not Rome. You're short on time in those two cities. From the logistical perspective Bologna can be part of your future trip that includes Florence.

Why not save Bologna and dump Sorrento; only 2 full days and lots of travel time.

I have not been to Bologna, but I would skp it this first trip to Italy. I liked the Sorrento and the Amalfi coast a lot. I agree to a day for Roime, Venice,

I'd either dump the Bologna part and add 1 day to Venice, 1 to Rome and 1 to Sorrento/Amalfi coast, or dump the Amalfi coast piece and add those days to Rome and Venice. The AC region is well deserving of a future trip when you can give it the time it deserves.

2.5 days isn't enough for the coast. 1 full, non-jetlagged day isn't enough for Venice. My personal minimum for Rome is 4 nights/3.5 days.

You don’t need a day for Pisa. You can see all of the components of the Field of Miracles; tower, cathedral, and baptistery in half a day. Lucca, on the other hand, could use more time.

In Pisa make sure you see the Campo Santo too.

It looks to me that you are underestimating time and strain spent in transit. For example, first consider Lucca to Siena is 2 hours and half with 2 changes or 3 hours with a single change. Then consider doing it with luggage.

And on that note, going from Siena to Sorrento is another slog. Going from Siena to Naples is at least one train change and takes at least 5 hours, then you have to change to the local metro train (Circumvesuviana or Campania Express) which runs every half hour at best and takes up to 1.25 hours to get to Sorrento. Even driving is at least 5 hours.

Pisa there are all kinds of things to see; and one can google for 8 self-guided walking tours:

https://wikitravel.org/en/Pisa

With respect to hill towns in Tuscany, it is better to stay in the Val d'Orcia rather than Siena:

https://www.wanderingitaly.com/maps/valdorcia.html

An Avis car can be returned in Chiusi [not Sunday], train time to Naples 3:19 with a change in Rome. Unless the Sorrento hotel is very close to the station, a driver [e.g. Sorrentocars] would be expedient. The Circumvesuviana train is downstairs at Napoli Centrale. On that train you need to hold on to your luggage because of thieves.

I have been to all the places you listed and more.

1) Why so much time in Bologna? We visited it and it was OK, but we were not wowed. To me it is second tier in Italy. You don't need three days there in any event.
2) I love Siena, but why so much time there, cut a day.
3) Don't see amazing Florence on your list???!!!
4) Your visit to the Naples area is too short, add a day.
5) Rome deserves much more time. Add 3-4 days.

Some good suggestions on here. Think I will add days to Venice, Sorrento, and Rome.

Question: Is there a good home base in Tuscany that a) is car friendly, b) has plenty of food options that are walking distance, and c) would allow me to take an easy train into Florence one day?

In general I prefer to spend a minimum of 3 nights in a hotel - giving you 2 full days in each location. To me- your agenda is way too much travel and changing hotels time. Having said that, I am on a RS Tour now, and his tours usually only stay two nights. To me the difference is, I'm not concerned with the travel arrangements. My usual disclaimer - I get a whole lot wrong, and we all have our own preferences. Enjoy.

Travis, see my Val d’Orcia link. Montepulciano is the largest and we prefer the Locanda San Francesco, 7 rooms overlooking the valley with parking on site. A Florence day trip would best be done earlier, as there are local villages to concentrate on.

I've been reading the feedback on Bologna with interest as we plan to stay there for our first time this fall. However I did a similar trip to yours with 3 kids a many years ago and think most of it is good.

I would add one night to Venice and take one from Bologna. In regards to your question re Florence, you could daytrip there yourself from Lucca or stop on the way to Lucca via train.

As you have a car in Siena, you might want to consider picking it up in Lucca to speed up the transport time.

Your longest day that I see is Siena to Sorrento. I'm not sure where you connect from Siena, but you will finish in Naples and then have to switch to the Circumvesuvia to get to Sorrento. I wonder if you could drop your car somewhere to shorten that journey.

Travis-this link offers info on side trips from Sienna that don’t require a car and has info on eating, etc. https://www.discovertuscany.com/siena/what-to-do/day-trips-from-siena.html.
Having to rent for just three days seems a bit of time/money use that could be better utilized?

We recently spent a night in Padua and a night in Venice. Our B&B host in Padua (who was AMAZING) told us he thinks more people should stay in Padua and take the train to Venice for a day trip. (The regional train from Padua to Venice is about 5-6 euros and takes 30 minutes). After dragging my suitcase over steps and bridges in Venice, I think I would agree with him. We were not able to get in the Scrovegni Chapel, but the sights we saw in Padua were great. Thinking we were near where Copernicus studied medicine and Galileo taught was pretty cool!! And just now......reading that St Anthony's TONGUE is in a reliquary in the Basilica of St Anthony......well, goodness......hate I missed that! (The B&B we stayed at was Casa Camilla. I would recommend it to anyone...the hospitality was beyond gracious...)

I'll be the voice of dissent and say that I visited Bologna on my first trip to Italy and loved it so much that on our next trip, we spent time in Modena just to revisit the region. It certainly depends on your interests but if you're a foodie, this region is unmatched. I will say that we preferred our stay in Modena over Bologna. There's also plenty to fill your days--we spent a month in Italy last summer and one of our favorite days was the one we spent on an AirBNB experience to Reggio Emilia to see a parmiggiano dairy farm. I would cut the Amalfi Coast before cutting Emilia Romagna.

I love Bologna and the food, but I agree with others that Venice and Rome each need more time. I would either scrap Bologna or Sorrento. Amalfi will be very crowded in summer, and Pompeii will be miserably hot. 2 nights in Lucca is good, as is 3 nights in Siena, just be aware of the parking in Siena, it is outside the city center.

Based on some great suggestions - and family input - version 2.0 is available for your analysis:

Day - Activity (Overnight)

1 - Depart for Venice late PM

2 - Arrive Venice early AM (Venice)

3 - Venice (Venice)

4 - Train to Florence (Florence)

5 - Florence (Florence)

6 - Lucca (Florence)

7 - Train to Chiusi (Montepulciano)

8 - Tuscan Hill Towns (Montepulciano)

9 - Tuscan Hill Towns (Montepulciano)

10 - Train to Sorrento (Sorrento)

11 - Capri (Sorrento)

12 - Amalfi Coast (Sorrento)

13 - Pompeii (Sorrento)

14 - Train to Rome (Rome)

15 - Rome (Rome)

16 - Rome (Rome)

17 - Rome (Rome)

18 - Flight home

Looks great

Assume you will pick up a car in Chiusi?
I’d just get the car in Florence then return in Chiusi

I thought about Florence, but pick-up/return in Chiusi at least appears to be easier. Close to Montepulciano and we don't have to backtrack to Florence before heading south to Sorrento on the return day.

That plan looks better to me, personally. I've heard great things about Bologna, but Florence is so spectacular, it seems counterintuitive to me to go somewhere "second tier" (although - don't get me wrong - 2nd tier in Italy is still amazing!!) instead of a "first tier" city that's so close.

PS, not sure when you'll be in Florence, but if you're there before July 31, there's a digital art exhibit in Palazzo Strozzi that might interest the younger ones in your group. At a minimum, you should pop into the courtyard (free) to see the giant digital art instillation. We were there last week and thought it was fascinating. (For more "traditional" art lovers, the Donatello exhibit is in the same location, but on a different floor.) https://www.palazzostrozzi.org/en/archivio/exhibitions/lets-get-digital/

Have a great trip!

Be sure that the rental agency in Chiusi will have the type of car that you need
and check their hours

Well, the flights are booked and lodging reserved. This is the plan for June 2023:

Day - Activity (Overnight)

1 - Depart for Venice late PM

2 - Arrive Venice early AM (Venice)

3 - Venice (Venice)

4 - Venice (Venice)

5 - Tuscany (Montepulciano)

6 - Tuscany (Montepulciano)

7 - Tuscany (Montepulciano)

8 - Florence (Florence)

9 - Florence (Florence)

10 - Amalfi Coast (Sorrento)

11 - Amalfi Coast (Sorrento)

12 - Amalfi Coast (Sorrento)

13 - Amalfi Coast (Sorrento)

14 - Rome (Rome)

15 - Rome (Rome)

16 - Rome (Rome)

17 - Rome (Rome)

18 - Flight home

I could use some guidance on the following:

• I want to pick up the car at some point on the day I leave Venice for Montepulciano. What are some easy options for this? NOTE: I'd prefer Hertz as I get a nice rate with them.
• Was thinking we'd take the ferry to/from Naples and Sorrento as opposed to the Circumvesuviana. I think the little one would enjoy the boat ride. Anyone done this? How'd it work out?

This was pre-pandemic, but I took the ferry from Naples to Sorrento and it was just fine. I had flown to Naples so took a bus from the airport to the ferry dock. When you arrive in Sorrento you are in the "little harbor" and need to go up to the town, but there is an elevator which at the time cost 1 euro per person, if you don't want to take the 100+ steps on the staircase.

The order is a bit awkward
Would be easier/smoother to go to Florence from Venice
Then pick up car as you leave, then Montepulciano and drop it in Chiusi

I don’t think there is a “good” place to get the car between Venice and Montepulciano
I suppose you could get it in Venice.
But that seems a long unnecessary drive

Taking the ferry from Naples to Sorrento requires a taxi ride from train to dock
It’s already a pretty long trip from Tuscany so you are adding at least 2 more “seats” to the trip, actually 3 because you also have to get from dock up to Sorrento to your hotel ( taxis or bus) or climb/walk if elevator isn’t working

You’ll have opportunities to ride ferries while in Sorrento /Amalfi

I need to be in Florence on those days because that's when my son is arriving from US, and he would rather see Florence than Tuscany.

I think we will take the train from Venice to Florence airport and rent and return the car there. Consensus seems to be that this is a good location if you intend to hit the road and head somewhere other than Florence. Hertz is there, and I'm getting good rate quotes despite the warnings that airports are more expensive.

Turns out the guy I'm renting from in Sorrento will provide private transfers to/from Naples, so ferry is out.

I like your itinerary but I'm sorry I was late in seeing this .... Bologna would have been great for a day or two. We loved our time there. BUT that said this latest itinerary looks good.