Itinerary Help

The only difference being having a day trip from Florence versus an extra day in Rome, I'd poll the family.
We would know what you want to see in the two cities to compare, but I think skipping the day trip might make it feel like you are moving less than you are.

I think both look great. I agree with last post about polling your family. Personally, I like more time in Florence but that is our preference. Your going to have a great time no matter what. I would suggest when your going to Capri pay attention to the weather or ocean report. To see if the water will be rough on that day to see the "Blue Grotto". The only reason I mention this is because out of three separate trips to Positano, I planned a day trip to Capri. I wanted to see the "Blue Grotto". However, each day trip to Capri was set in stone. I had other things to do on different days. Each time I went to Capri the water was so rough they did not let us go into the cave. It has been a number of years since I visited that part of Italy. Next time I am in that area. I am keeping my Capri day trip flexible. It is the one thing I wish I seen. Don't get me wrong, Capri is nice but I wanted to see Grotta Azzurra.

Safe Travels

I’m going option A, if only because a day trip out of Florence feels like a bit much on this itinerary. Just that you’re going a fair bit of travel, so getting on another bus/train for part of that day feels like a drag. You can see a lot of Florence in two days with aggressive and organized sightseeing. So, two full days isn’t necessarily short-changing it either. I’m in the minority, but magnificent art treasures aside, I didn’t find Florence itself particularly attractive or interesting. This is especially true in contrast to Rome. But both itineraries look solid.

Yes, I've read about watching the forecast for Capri. It doesn't seem like we'll need to pre-book any of the day trips from Sorrento, so we should be able to flip those days around any way we want at the last money.

I should mention that we arrive via direct from to Rome and then are going right to Florence so that's a little extra travel. We do have a direct flight from US to Rome though.

Accomodations are all booked using option A at this point. I'm sure I can rebook everything if I wanted, but bit of a pain. That being said, I'm still not fully convinced on A. It sounds like we can do Florence with 2 full days without short-changing the city too much. If we were going to do an extra day there, we'd probably do something like this
https://www.viator.com/tours/Florence/Small-Group-Wine-Tasting-Experience-in-the-Tuscan-Countryside/d519-5292P25 I'm not that concerned about the extra travel in a van out to wine country. I'm more concerned about short-changing Rome. We don't have to do a day in Tuscany to have a great trip, but we do need to make sure we have enoguh time to enjoy Rome and I'm not sure if Dinner, 2 Full Days, 1 half day, 3 nights is enough in Rome.

2025 is the year of the Jubilee in Rome. My guess, Rome and Florence may be extra crowded if that is even possible. I suggest you sit with your family and make a list of all the sites you want to visit in Rome. Not only will it be crowded but also hot. If you think you can see everything in 2 full days then go with option B. If not, then option A it is. Enjoy