Itinerary Suggestions, Please

How about:
3 nights Venice
3 Florence
3 Siena
3 Sorrento
6 Rome
?
Three nights gives you two full days.
What time of year are you going?

I think the itinerary proposed by inbsig is good; however, I suggest one modification. If you take one day either from Rome or Siena and add it to Sorrento, you and nephew could do some hiking on the Amalfi Coast or Capri. The views are nothing short of stunning. I am not so big a fan of Siena as are some on this forum. If you just see it as a day trip from Florence, you will also have another day for that city and save yourselves the time lost to packing up and moving.

I'm going to assume you have reasons for 2 nights in Milan, so I won't suggest changing that, but I would agree with scrapping Vernazza. I'd also scrap the 2 nights in Siena. Give an extra day to Florence, and visit Siena as a day trip. Then add a day or 2 to Sorrento and the rest to Rome.
Milan 2 nights

Venice 3 nights

Florence 4 nights

Sorrento 4(5) nights- hike on the AC, visit the AC towns, see Capri and Pompeii

Rome 4 (5) nights depending on the time in Sorrento

Thanks for the helpful suggestions- much appreciated! I just changed our inbound flight to Venice (thank goodness I bought changeable/refundable!), omitting Milan from the itinerary. I'm thinking:
4 nights Venice
4 nights Florence
5 nights Sorrento
5 nights Rome

It's certainly much more simplified. Could it be better? Is Orvieto a good day trip from Rome, or is it better to stay overnight there? Once again, thanks for the help!

Hi Sara -
What a great trip you're going to have! If I was to make a suggestion, it would be to keep the CT and put Sorrento on the back burner for another trip. It's sort of your outlier, and there's enough in that region to see/do to give it more than just 3 nights. Yes, the CT will be busy but less so in the evenings when the day-tripper leave. You can also avoid the worst of the masses by hiking trails most others will skip. In other words, give the overrun "Blue Trail" a wide berth in favor of some others. Folks here who have trekked some of them can give you some great ideas! We found the villages themselves to be reasonably quiet in the early mornings; well worth getting up for a knockabout. :O)

Give Rome another night; I consider 4 nights/3.5 days to be the minimum for that one as there's so much ground to cover. You will only scratch the surface in 4 nights but will be able to do it a at bit more leisurely than with 3. Heck, you could even give it two more nights for 4.5 days; spend the extra day hoofing the fascinating Appia Antica, our favorite Rome adventure to date, and lots to see along the way.

https://www.parcoappiaantica.it. (if it doesn't come up in English, click the orange "translate" button in lower left and choose the British flag.
https://www.parcoappiaantica.it/smart-info-ita-eng/

I'd also add a night/day to Florence, or two if not adding two to Rome. You and your young companion might enjoy a day trip to Lucca (easy by train) to either walk or bike the 2.5 mile path on the old city ramparts. This day could be as active or as laid back as you choose!

https://www.ricksteves.com/watch-read-listen/read/articles/lucca-italy

EDIT: Oops, Sara, you've posted a new itinerary as I was banging away. Will give it some thought....

Thanks, Kathy, for the great suggestions and resources!

I like your new itinerary. I am one of those Siena superfans referred to above, but at least with 4 nights in Florence, you’ll have more time for a day trip, and might be inspired to come back some day. I also loved Orvieto, great day trip, and would recommend staying overnight if you were spending more time in Rome than you are.

Thanks for all of the useful information- much appreciated! My final itinerary is:
4 nights Venice
3 nights Florence
2 nights Siena
4 nights Sorrento
5 nights Rome

In the end, I couldn't give up on Siena since it's one of Rick's "must see" places, and because of the feedback I have read in this forum. And Kathy, thanks for the "hoofing the fascinating Appia Antica" suggestion- we'll definitely be doing that!

Looks good!
I'm OK with you keeping Sorrento; it just needed more time than your original schedule, and you were able to do that by scrapping the CT. I'm not sure you needed to add to Venice; I personally would have tacked that 4th night onto Florence for that day trip to Lucca but heck, you're down to 5 locations now versus your original 7 so nice work!!!!

The Appia: I'll suggest jumping on at a point further out from urban Rome (ours was at Casal Rotondo) and walking back into the city. I might suggest springing for a cab to get you to one of those points 'cause our chosen method certainly isn't one I'd recommend for everyone! HA! Also, if you are really conditioned walkers you could take a bus to Ciampino airport as there is an easy jumping on point very close by there. That's what we'll likely do next time.

Some info to get you started:
Maps:
https://www.parcoappiaantica.it/wp-content/uploads/2021/11/mappa-completa-del-Parco-dellappia-Antica-ENG.pdf

This map page linked below also includes open/closure days for some attractions along the way:

https://www.parcoappiaantica.it/wp-content/uploads/2021/11/Brochure-A-park-unlike-ENG.pdf
I'll suggest seeing one of the catacombs? (We did Sebastiano but Callisto is a good choice too). Good stuff for history teachers on both Roman pre-Christian and early Christian burial practices, and your companion is likely to find one interesting as well.

Print this next one out for sure! It's what we used to tell us about most of the piles we were seeing alongside the road, It could probably been picked up the park's Visitor Center but as we started our walk backwards, that wasn't an option.

https://www.parcoappiaantica.it/wp-content/uploads/2021/11/via-Appia-Antica_ENG.pdf

Pack beverages, snacks, wet wipes and a small trash bag along, and head out early in the morning. Nothing like a nosh in the shadow of a crumbling, nearly 2000 year-old tomb!

Editing to add: if you day trip to Capri during your stay in Sorrento, do the hike/walk up to Villa Jovis:
https://www.capri.com/en/e/the-villas-of-tiberius

With 4 nights in Venice, you’ll have time to take a vaporetto (with a vaporetto pass, if you don’t already have them) out to some of the islands of the lagoon. Burano and Torcello are my favorites. Torcello is very quiet and non-hectic, as well as historic.

Thanks again, Kathy, for the great resources! I have them bookmarked and copied. Given Trystan's passion for walking and my interest in early Christian and Roman history, this walk is going to be a highlight of the trip, I'm sure. Sorrento is important because of Pompeii and Paestum. CT will have to wait for a more off-season trip with they hubby that includes the Tuscan countryside- and Lucca!

I decided on 4 nights in Venice because it's our jet lag city, and because I hope to take a watercolor painting class from a local artist. Thanks lnbsig for the Burano and Torcello suggestion. I think this will be a must!

Sara

If you do make it out to the Burano island at Venice then there's a somewhat famous Restaurant there that would be good for lunch/dinner.

Trattoria da Romano

https://www.tripadvisor.com/ShowUserReviews-g1597326-d1516263-r146236758-Trattoria_da_Romano-Burano_Veneto.html

First saw it on one of Anthony Bourdain's travel shows. Other people seem to like it as well.

https://www.tripadvisor.com/ShowUserReviews-g1597326-d1516263-r146236758-Trattoria_da_R