Looking for a few suggestions

Scott, it's uncertain exactly what sorts of "suggestions" you're looking for? Could you clarify, please? :O)

I will mention that if you're looking at 4 nights in the CT during peak high season with a family of four, you need to put some urgency on finding and booking your accommodations. That region books up fast and early before the season: we've seen posters who were having trouble in January finding suitable rooms for May. If you can't find anything in the CT, try Levanto. If that doesn't work, try La Spezia.

Overall I think you have a nice pace. Let’s lay it out move by move.

July 31 arrive Lisbon, 6 N

August 6 fly to Venice, 3 N

August 9 train to Florence, 4 N

August 13 train to the Cinque Terre, 4 N

August 17 train to Rome, 5 N

August 22 fly home

It will be hot so moving slowly and allowing lots of time is key. Enjoy lazy afternoons and embrace evening activities. The Cinque Terre can be quite charming after the day trippers leave. There are things to do at night in Rome, too, after the heat of the day has passed. Make sure you have A/C in your lodgings!

We are heading to Italy in July as well with our 12 year old and 20 year old who has autism. We are planning a slow pace as well, due to the autism, as well as crowds and heat. Our "place we can just relax" is going to be Ischia. We are buying tickets ahead for the important stuff, but not over scheduling. 20 year old loves volcanoes and Roman history, so we are planning the trip around his interests (Colosseum, Pompeii and Vesuvius) and leaving plenty of free time to chill, plus doing our research to find off-the-beaten path places (e.g., ship museum in Venice, Tomb of the Scipios in Rome) and things that are open late (e.g, Doge's Palace) to avoid crowds and stay cool. Also bringing along books and movies to keep him occupied if things go bad!

Scott and clange: Be aware of the heat - the incredible heat - in much of Italy in July, especially in places with no shade - which includes Pompeii and Vesuvius. Those are places where you will want to go FIRST thing in the morning! Florence, too, can be surprisingly stifling; it's in a valley, and just soaks up the rays. Plan lots of rest stops and gelato. And drink lots and lots of water. Many Italian interiors, like restaurants and museums, are not air conditioned to the extent that such places are often cooled in the States. I've been very glad to have a paper fan with me, for example, in the Uffizi.

I feel like Debbie Downer today. The Cinque Terre you visited 20 years ago do not exist. Over the last 10 years the CT has become a very popular tourist sight, especially for day trippers off mega-cruise ships. Both Florence and Venice will also be very crowded during the day at the main sights and the center. Canareggio and Dorsoduro areas of Venice are less touristy. I'd add another day there and take it slow, exploring the back canals during the day - and a gondola-rowing lesson. Bologna is a good place to settle in for several nights. It's not a big tourist destination, so it is probably going to be less crowded and it's a major rail hub, so there are lots of good day trips.

Thank you all for your suggestions, we are still up in the air to exactly what we will do, but I think we will eliminate Cinque Terre:( Venice is a non-negotiable and of course Rome is necessary as we fly from there, so we will do a week+ in Portugal and then have 2 weeks to do Venice, Rome and somewhere else?

Thoughts are to fly from Lisbon to Geneva, spend a 4-5 days around the Lauterbrunen Valley, then train to Venice or fly to Venice and maybe a ferry to Crotia? I need to start booking, we need to get our family on the same page:)

I like that you're slowing your trip down a bit. Croatia is beautiful and the Adriatic is stunning but it is somewhat difficult to get from Venice to Croatia and back -- it's doable but not easy. Once in Croatia, you really need a car -- the roads are excellent and it's easy to drive there. You could fly from Split to Rome (I assume). I use the website Rome2Rio to figure out my transportation options.

Another thought is to rent a car and spend a week in the Tuscan or Umbrian countryside, at a place with a pool. You could visit small towns, hike, go to the thermal baths, visit a working farm -- lots to see and do. Just a thought!

Enjoy your trip!

A farm stay might be fun, somewhere near Rome. www.agriturismo.it/en

We are planning a ferry from Pula, Croatia to Venice this summer. It looks like there are lots of options from various cities along the Croatia coast, but they don't go frequently - sometimes just 3-4 times a week each direction, so look at those carefully when planning. www.croatiaferries.com