Family itinerary help

Fly in Venice
-take a car at the end of Venice visit
-Go to Verona
-Go to Milan
-Go to Cinqueterre
-Go to Pisa
-Go to Orvieto
-Go to Pompei
-Go to Rome and drop the car

It depends on the pace you think will work for you, but you could do it all. Time of year would determine if I went north to south or vice versa (Into Milan or Venice, out of Rome or Venice). So, group it together by location, and then eliminate the outliers (based on transport or geography reasons).
For a more relaxed pace, if you can find an alternative to Pompeii (well nothing can really compare, but you can certainly find other impressive ruins to see), then you would not have to go that far south. I consider it too far for a day trip from Rome, but it is doable--or there is Ostia Antica outside Rome. If you stick with Pompeii, you could eliminate Cinque Terre and do the Amalfi coast instead (the hiking is even better imo).
Perhaps spend some time on the trenitalia website--this one is a bit of work!

First, I'd forget the car. Everything can be done using trains and it's a lot less hassle. Fly into Venice, then to Verona, Milan, the CT, Pisa, Orvieto, Rome and then fly home. Forget Pompei as it is a bit out of the way and will require backtracking.

Yes, it does seem like Im trying to do a lot for 3 weeks. Pisa and Verona could be easily be done as day trips, though. And I could easily cut down on the number of destinations. It'd be nice if only moved to a new destination every 3-5 days.

Most likely this trip will take place next July, since we have to deal with school and college schedules. I figure at that time of year it's not going to matter whether we start in the south and head north, or vice verse. Or does it? Does it just get hotter and hotter as the summer drags on? I've only been in May and late October/November, so I'm not sure.

I hadn't thought about a car rental. My previous trips to Italy I took trains and buses everywhere because it was just I, or I and a friend. I guess a car makes sense for a larger group... especially since I'm aware that at least 2 people in our party are time wasters and feet draggers. But I don't know if I want to deal with the hassle of a car rental. One hears so many horror stories!

This is what I've come up with so far, with your suggestions in mind:
Rome 4 nights
Sorrento 3 nights
Orvieto 2 nights
CT 2 nights
Quick stop in Pisa
Florence 2 nights
Venice 3 nights
Verona 2 nights
Milan 2 nights

This definitely needs some work!

OK, here's mine. First drop Pompeii, too far south.
Fly into Venice (Nights 1 -4), 2 days in Venice plus
Train to Verona (5&6)
Train to Milan (7&8) Duomo, Last Supper, Galleria, Quadrangle, etc
Train to 5 Terre (9&10) See towns, swim, hike
Train to La Spezia, rent car, drive to Lucca (11-13), day trip to Pisa, Devil's Bridge, Montecatini Alto, etc
Drive to Siena, via Volterra (am), San Gimignano (pm), arriving evening (14&15), see Siena
Drive to Orvieto (16-18), see Orvieto, day trip to Todi, Montefalco, Assisi, Carsulae Roman Ruins, Spoletto
Drive to Rome (19-21)
Fly home from Rome
I have done most of this trip in one form or another. You can drop any location you want and add time wherever you want. It is a lot of moving around but that is why you have a car, to minimize the hassle of moving around. Plus, you get to see a lot more with a car than just a few cities. Trains and buses take time and coordination, although both are wonderful conveyances in Italy. I love using a car to maximize experiences. Driving is easy in Italy.
A note about Carsulae, they are Roman ruins on the Via Flaminia and very lightly visited. You will have them to yourselves likely. Google it.

Have fun. Drop a message if you want to discuss.

My two centissimi

Fly into Venice - 4 nights, get over jet lag
Train to Verona - 2 nights. If you go early in the day you have time to see it, then rest, then opera which is late. Next day, take a day trip to Milan for the Last Supper wish list item.
Train to 5 Terre - 3 nights
Train Orvieto - 3 nights. Stop in Pisa on the way. You'll have to leave early and plan carefully, but it is possible. If the goal is to see the tower, it is enough.
Train to Sorrento - 3 nights
Train to Rome - 5 nights
Fly home from Rome

That is 20 nights, not including the night of the overseas flight, so three weeks. It is a fast pace so if you want to relax more, drop something. Try to go in June, not July or August.

My 2 cents would be to follow Laurel's schedule. Minimizing the number of 2-night stays will definitely be a plus when moving 4 people - and two of them foot draggers - around. I also like ending the trip with 5 nights in Rome: it'll give you a nice long stretch to catch your breath before heading home, and there's a LOT to see in that one. You'll be be dealing with July heat and crowds so not having to rush around to cram everything into a short couple of days will make it less wearing for all.

Thanks for all the great advice!!! This board is the best 😎

After a short discussion with the husband, he's decided to drop CT in favor of more time in "Tuscany" and Amalfi coast. So I'm thinking it's best to start in Milan to get those few "must see" things out of the way, then head east, then south, ending in Rome.

Would it be a good idea to do Verona as a day trip from Venice? How would that work out if we went to the opera? Or I suppose there are music venues in Venice as well. Vivaldi, etc. I should look into La Scala in Milan as well.

I'm liking the idea of a car just for Tuscany. As one person mentioned we could see a whole lot more that way. Hubby would LOVE that! maybe stay at an agritourismo. I've always wanted to go to Volterra, but bus and train travel to there was spotty. I'd also love to see Ravenna.

How would this be... pick up a car after Venice, visit Ravenna, maybe a few other stops around Umbria and Tuscany, then drop the car off near Orvieto, then head to Sorrento and finish in Rome.

I think I'm making progress here!

I came up with 2 different itineraries:

2 nights Milan, 4 nights Venice, 2 nights Florence, 5 nights in an agritoirismo exploring Tuscany and Umbria by car, 3 nights Sorrento, 4 nights Rome.

Or 100% by train:
2 nights Milan, 2 nights Verona, 3 nights Venice, 3 nights Florence (includes Pisa day trip), 2 nights Orvieto, 3 nights Sorrento, 5 nights Rome.

Any fine tuning you can suggest? Obviously I'd need to hammer down more details if I go with the first itinerary. But this is fine for now, and we shall have a family meeting to discuss this very soon.

Would it be a good idea to do Verona as a day trip from Venice? How
would that work out if we went to the opera? Or I suppose there are
music venues in Venice as well. Vivaldi, etc. I should look into La
Scala in Milan as well.

What about opera in Rome instead? It's too early (probably?) for next year's dates but here's what ran at the Baths of Caracalla this summer:

https://www.romeing.it/festival-caracalla/

I'd be cautious about shorting Florence or cautious about how you schedule your dates there. You don't want the single full sightseeing day planned to be the one that the major museums are closed, if those are on your list.

My family just came back from 3 weeks in Italy. My kids are 10&13. With all the help from this board this is what we did.

Flew into Milan
3 nights in Como (went to Bellagio)
Took the train to Rome for 4 nights
Train to Florence for 6 nights
Train to Bologna 2 nights (this was one of our favorite places)
Train to Venice for 4 nights
Train to Milan for 3 nights

We stayed at airb&b's which worked out great for our family they all had washing machines also
We each had a carry on suitcase to get around easier

We wish we could have seen so much more or gone to more places but knew that would make it a crazy and not so enjoyable vacation. We really loved our vacation and didn't want to leave. Traveling by train was so much fun and we loved interacting with the locals. In Bologna it was movie night at the piazza with American subtitles. Sorry for going on.

I didn't visit Verona during opera season, but it is one of my favorite Italian towns. I met a couple who went to the opera and they said it was a great experience even for a non-opera lover (as one of them was) because of the venue. The opera ends late a night so unless you have a car or are staying the night, it's a non-starter.

In general, take into account the amount of time it takes to change locations (figure about 1/2 day on average, what with packing, getting to train station, etc). Remember that you can only go as fast as whoever happens to be slowest at any given time (sleepy-head, gawker-walker . . . ). 3 weeks is a long time to be on the road. It's tiring to change locations often, you'll need to buy supplies, do laundry, etc.

Thanks for all the help!

Turns out the 19 year old already has a ton of plans for next year, so she wants the trip to be much shorter. Of course we still want to see and experience a lot. If we cut the trip down to 2 weeks we would just have enough time for Venice, Florence, a couple nights in CT, and Rome. Or we may just end up doing a Mediterranean cruise out of Rome, and tack on a few days before and after for Rome and Venice. Oh, the fun realities of having a grown up daughter!

Renting a car is an option in Italy, but finding parking will be problematic or very expensive in the larger cities like Milan, Rome, Florence. Also, if you drive on the autostratas, the tolls are huge.

In any event, if you still want to rent a car, I highly recommend not taking in south to Rome and Pompeii.

Of course we still want to see and experience a lot.

Angela, if you've been on a cruise before then you have a handle on the drill but if not, the ability to "to see and experience a lot" is precisely why we don't do them. The ships usually aren't in port long enough to do much at all (in any depth, anyway) and ports can be a loooong way from the cities advertised. Civitavecchia and La Spezia, for example, are not Rome and Florence!

Shore excursions are also very, very expensive - this forum sees ???s all the time about how to avoid them - and it takes the same amount of digging to strike out on your own as it would if you were staying in those locations; more, actually, with sorting transport to-and-from the ship and figuring what you can do with the little time allotted.

IMHO, your young people will have a richer experience in the art of travel if you choose the other option you're considering (Venice, Florence, a couple nights in CT, and Rome). You'll also have far greater flexibility to work around weather and attraction closures with multiple days in each place. It's no fun if the only day the ships give you to do ___ is the one that pours rain or that the major museums are closed?

Italian trains are fun and I'll bet your young people will enjoy them! They'll be very easy to the 4 locations on your list, and inexpensive as well if you can land super-economy/economy tickets in advance.

We've cruised the Med., and have traveled quite a bit in Italy on the ground. Agree completely with Kathy about it being a much more rewarding experience on land rather than by sea. If you do cut back to two weeks, then Venice, Florence, the CT, and Rome should be more than enough to cover the high points without wearing yourselves out.

Send the 19 yo home early and enjoy the three weeks. Her loss.

Those are some excellent points. I do know some about cruises, although my experience is limited to Alaska and Hawaii. And yes, I'm sure I could manage the few ports in Italy since I have been to Pisa and Naples before... but the stops in other countries not so much. The cruise would also go to Cannes, Barcelona, and Palma de Mallorca (which I admit is a bit of waste of time on our ITALY trip). And we would experience some on the ground travel as we would take the train from Rome to Venice right after the cruise.

But you're right, we would have a much richer experience doing things on our own. We can do things at our own pace. Search out the little artigianale gelato shops, and eating the local cuisine instead of stuffing our face at the buffet every night. The cruise may sound like a great deal, but there are a ton of hidden costs.

So I made a few assumptions about our most likely travel dates for next summer and went ahead and booked apartments. I added a few extra days in Rome and Venice, and figure I can easily adjust the dates if needed after we've got our plane tickets. The exact dates of the cruise I divided between CT (3) and Florence (4), so should we ultimately decide to book the cruise I will just cancel those apartments.