Pick up the pace: Italy itinerary advice for the “slow traveler”

Sounds like fun! Four night stays are nice. To me this looks like a fun intermediate stay-length itinerary.

I think those times will be fine, but it's going to be hot, especially in Rome and (probably worse) Florence, so you may need to scale back your expectation for how much you can cover in 3 days and a few hours.

I like Orvieto a lot.

Read hotel reviews with an eye out for comments on the quality of the air conditioning.

I fully approve this itinerary. As noted, sure to be hot, but the days are long. Figure on morning/evening sightseeing with a siesta between. Have fun!

I think it is doable, but do a detailed itinerary. For instance, will you train from Rome to Orvieto for the first night, then stay the next night? That only leaves you one day at Orvieto.

Personally I'd cut Monterrosso. It will be incredibly crowded that time of year.

It's funny we used to fast travel, then dropped to slow travel, only staying in one place. We just took a faster trip with a local college group to Vienna, Ljubljana and Salzburg. The trip was 12 days on the ground. Even at that, moving and traveling 4 times was more than we care for.

Putting in a suggestion to take a day trip to Via Reggio, a beach town, from Florence. It's lovely and will be a nice break

Thank you, all, for the feedback. We are giving this itinerary a try!

Perfect allocation.

For Venice 4 nights might also afford a day trip to the lagoon islands (Murano and Burano) or Padua.

Just be aware that if the farm is too far from the town in Orvieto you might need a rental car, which, with a kid under 12 would require a baby seat or booster (depending on age, height, and weight), which adds to the rental cost (about 30 euro/day for a full seat).

Thank you, Roberto! We are staying at Podere Sette Piagge, which is within walking distance to Orvieto, although it is more like an up hill hike than a casual walk. We three are in good physical shape so not concerned about the hike. My 15 year old will probably run up the hiking trail in fact!
https://poderesettepiagge.it/en/

Looks good.

The only tweak I would give consideration to is to add one more night to Rome ( at the expense of Venice).

With a Noon arrival from PDX, Rome really has less time than either Rome or Venice, and Rome has a lot to offer.

The walk up to the city center is on a very dark and steep country road. Take a flashlight with you. Or even better, ask the host if they can arrange a taxi. It's not an ideal route for a walk, even if you are in good physical shape. There are no sidewalks.