3 week Italy Itinerary help/check please & Thank You!

I think this is a well paced trip with long periods of time and the chance for day trips from Florence if you want to do that.
From Florence I would consider trips to Siena, Bologna, Pisa, and Lucca if that interests you. You will get a lot of rural Tuscany but Siena is the closest thing to rural Tuscan city and is worth a look all it's own.

You will need a car for any kind of serious Tuscany/Umbria exploration. You can rent and return to Florence with easy access to the train and avoid the drop-off fees but if you are in southern Tuscany that's a trek back. Many people train from Florence to Chuisi - Chiusi–Chianciano to be exact - and rent a car there since you are only about an hour from Pienza and Montepulciano at that point. And the return the car there and continue on to Rome. This means taking the slow train to and from Chiusi–Chianciano but you should be on Tuscany time by then and very relaxed.

This is a good overview of where you can get in Tuscany by train and with bus connectors.
https://www.wanderingitaly.com/maps/images/tuscany-rail-map.png

Rural Tuscany is as beautiful as advertised.

If you are going to go to the Almafi Coast then October is the time to go assuming the weather holds out. But be sure you get there in October because when November starts everything - including the ferries - go into off season mode. We visited the end of October 2024 and the AC seemed a bit crowded to me but I know it was a tiny fraction of the crowds in season. I personally think it is amazing from the water but loses its appeal the closer you get since it is given over to seasonal tourism, but people love it and it remains wildly popular. In Amalfi there are still markets and shops that sell fishing line and boat supplies but also I counted 4 gelato shops in a row on the main square.

We stayed in Salerno and I personally liked the "hint of southern chaos" vibe but we were there for Naples, Pompeii and Paestum and did the AC because it was there and the weather was nice. So if you're going for the AC then I think you should stay on the AC. The Salerno vibe is not the AC vibe at all but is a good base for ferries and buses to the coast with fast train access to Naples and Rome.

Hope that helps, sounds like a great trip!
=Tod

The weather can be tough to predict, so I wonder about putting the coastal time earlier. Tuscany/Umbria should be wonderful no matter when you go.
Since you have a week and are interested in doing so, you could easily split your time between a smaller village/town and an agriturismo.
I will say that if I had not had interest in Pompeii and Naples, then I would have given Amalfi a miss and chosen a different coastal area with fewer crowds and lower prices. Just something to consider.

Thanks for all the great information!

@GeoffB- I have seen your trip report, looks like you had a fantastic trip and your tips are excellent.
@hiredman - I believe I read one of your forum comments before and that is one reason we are considering Salerno. I will look into your suggestion for train travel to Chuisi as well and yes we planned on day trips from Florence-initially were not renting a car or staying in Tuscany or Umbria..still working on where and how long ;).
@valadelphia-I will definitely think about your advice on coastal areas..we are trying to avoid the (instagram) chaos by going near the shoulder season if there is such a thing these days.

Thank you all for your assistance and advice, it is greatly appreciated.

We were in Venice, Bologna, Tuscany in March, 2025. We rented a car from Bologna, but renting from Florence is good too. We spent 3 nights in Agriturismo La Terra, Via Di Petrignano 2, 53045 Valiano, Italy (you can find it on Booking.com) It's right on the Tuscany - Umbria border. It was a little off the beaten path, but that was fine. From there we did day trips to Siena (~1hr drive), Montalcino (~50min) and Montalpulciano (~25 min). Cortona and Arezzo are nearby but we didn't make it there, and Perugia is less than an hour as well. They offer cooking class which was 90euro/person including a multi course dinner. They also offer dinner to guests (35 euro, best deal ever!) I think 3 days was the minimum I'd recommend, maybe 4 if you want to visit more places as day trips, then we drove to Lucca where we immediately dropped off the car (outside the wall) and did the rest of our trip by train. If you rent a car, consider doing one way drop off, it's more expensive but really when you factor in any backtracking you have to do to return in the same place, it's worth the extra. Just get rid of it before you stay overnight inside any city centers.
Our first trip to the area was in March, 2023. 6nights in Florence, 3 nights in Venice, 4 nights in Rome, all by train. We lost a night in Florence due to cancelled flight (planned 7 nights). Florence was wonderful, we were off season and got the Firenze card and spent most days visiting museums, it was great. There's never enough time in Florence but your schedule looks great for a first trip.

Just FYI all the day trips I suggested are all doable by train in about an hour or less. Oh, and you could also add Arezzo to that list.
I'm certainly not suggesting all of them or even more than one but you're probably in Florence long enough that if you wanted to add in Siena or some other place else you could.

Have a great trip,
=Tod

Thanks @sanomh for that information, I will look into the place you stayed and appreciate all your help. It's so difficult to choose as the more you look the more you want to see but one needs to realize you can't see it all and just enjoy each moment and take in the culture etc....easier said than done ;)

Thanks again @hiredman, I assumed you meant the day trips were by train. Florence also has a lot of tours but we are pretty confident on using trains within Europe thanks to the help of people like you on this forum who provide such great advice.

Hardest part is waiting a year to enjoy all this, thanks again all.

Cheers,
KS

I will just add advice regarding Tuscany and Umbria.
Siena, Pisa, Lucca, San Gimignano, Cortona and Volterra are worth a visit.
For Umbria, Gubbio, Assisi, Spoleto, Perugia and Orvieto are great. We particularly loved Assisi and Orvieto.

Thanks @geovagriffith, we appreciate all advice.

KS

It's always a little daunting to select a place to stay, especially agriturismos, if there aren't a lot of reviews. We found Agriturismo La Terra on booking.com, which is what i've used almost exclusively in Italy. So far, I haven't been steered wrong. I had one poor stay (in London) through booking.com - it wasn't a complete scam, just 'not ready for prime time'. That was partially my fault, there weren't enough reviews, only a handful, and they sounded suspiciously similar. I've learned my lesson, read through all the reviews, look for details that are specific enough to indicate a real stay, including some negative comments. I'll also look at google maps, sometimes there are different reviews that help make the decision.
Good luck.

Hi KS,
Fellow Canadian here! I just wanted to chime in to recommend the area between Chiusi and Fabro in Umbria. We just spent a week there and loved it. We rented a car from Florence and drove to Fabro. From there we either took regional trains (cheap and easy) or the car to explore the many little towns in the region. Parking at the train station was free. Local buses were inexpensive.
Aside from Cortona and Siena (at the end of the trip), we found the cost of eating out roughly 30% less than we'd spend at home, including the exchange.

Renting a car from Florence airport and getting out of the city was pretty straightforward and the highways easy enough to navigate. A week's rental was about $600 Canadian, including fuel. But that will, of course, depend on the type of car you get.
The only other thing I'd mention is that the hill towns are vertical -- at least the ones we visited in Umbria. Most did have a central area at top where you could stroll at night. But the ones without funicular or escalator access were a workout just to get from the bottom to the top. And in mid-September it was still 30 degrees and higher.
Happy planning!