Something similar to Orvieto from Florence

Orvieto is indeed stunning, especially the cathedral. You will love it. Regarding Florence, using public transport somewhat limits your access to the hill towns in the area, but you might consider Lucca (about 1.5 hours by train) or Siena (about 1 hour by bus). They are larger than Orvieto, and they won't be uncrowded, but both are easy to explore on foot. But Lucca is lovely for its medieval walls, which you can walk or bike, and its charming center. Siena is one of the most special towns in Tuscany, IMO. There's no place like it. And you can't do better than Siena Cathedral for "wow" factor. You won't have traffic whizzing by in either town, at least not in the areas you will want to explore.

Just curious, why is Bologna now off the list? You can reach it by fast train from Florence in under an hour.

Since your schedule is already so tightly packed, consider making Orvieto an overnight stop - or two - between Florence and Rome. A problem with day trips is that you spend precious time going both to and from, so you may gain some time by an overnight stay instead.

Often smaller towns are at their best both early in the morning and later in the evening, when the daytrippers are on their trains. So you should end up with a better experience, which appears to be important to you.

Lucca is almost the default on this forum and was my first thought, also. Easy to go by train, and the medieval wide wall is wonderful for renting a bike or walking. The city inside the wall is very nice for a day-trip, although I also stayed there several nights. It will be the busiest one of these three.

Ferrara will have less tourists than Lucca and is interesting and also an hour by train. (Choose the Frecciarossa option to avoid train connections & longer travel time.). Ferrara has a castle in the historical center and lots of nice restaurants. If you like archeology museums, there’s a very good one about the items uncovered from Spina. My adult daughter & I stayed here two nights and enjoyed it.

Arezzo is an hour by train from Florence, also. Go to the upper portion of the city for the historic piazza and some great food. Depending on when you’re going, Arezzo could be very busy if you’re there during their jousting festivals….but they are a lot of fun to attend!

I would go to Siena. Lucca is a pretty town but Siena is just prettier to walk around and Siena has wow inducing attractions like the Duomo and the Piazza del Campo that Lucca cannot match. Every inch of the Duomo is filled with great art from the facade to the floor to the roof. The Piazza del Campo is the best piazza in Italy, it’s great place to have a drink, relax, and people while facing the Palazzo Pubblico.

If you’re looking for “little to no crowds/tourists,” then lucca and Sienna won’t work. Their charms attract lots of both.

Then there’s Assisi (town of St. Francis), but you’ll get crowds, and also traffic whizzing by on very narrow streets with no sidewalks - very unnerving to be a pedestrian there.

Very close to Florence is Fiesole. It’s been on my visit wish list for some time, but I haven’t made it there yet. As such, I can’t guarantee what it would be like as far as crowds, but it should be a relatively nice break from the intensity of Florence.

Any town with no crowds is going to be harder to get to, i.e. you'd need a car.

If it were me, I'd choose Siena.

Last year I had a free day in Florence so I went to Pistoia, less than an hour by train.
It was market day, so lots of local people out shopping, a couple of great churches to visit, a stop for coffee, and back “home” again to Florence.
And no other tourists!

Perugia and/or Assisi

Pistoia is good choice but I'd choose Arezzo.... I really like it and it is compact and beautiful. There can be tourists but the Italians outnumber the non Italians. Prato is another easy train ride from Florence and is easy to walk around. Both are very short train rides. Orvieto is one of my favorite cities and I've been many times..... I would stay over night there if possible. Lucca and Siena have a lot of tourists.

Thank you all for your responses, as always they're greatly appreciated! I am busy researching each and those that didn't appeal to me in the past, I am giving a second review.

My trip begins in Venice for 2 nights, onto Florence for 4 nights, Naples for 4 nights and ends in Rome for 5 nights. Overnighting elsewhere is not an option, as you can see there is no wiggle room whatsoever without loosing valuable time in each of those locations.

I have not taken Bologna off my possible day trip locations. Bologna piqued my interest far more than the other day trip location mentions in guidebooks and online searches. But I am thinking it may be a bit busier than I would prefer.

I did come across the flower town of Spello. Charming, not many tourists, flowers and flower pots everywhere, but not so sure if they would be as beautiful October 4-8.

I will ask again when I come up with more questions.

Thanks again!

Personally, I think 4 nights in Naples sounds long. Instead of making Orvieto a day trip from Rome, could you consider overnighting there en route from Florence to Naples, and spending 3 nights in Naples instead? With 5 nights in Rome you'll have little time for day trips - too much to see and do right in the city.

Spello looks lovely but you'll spend almost 3 hours each way on the train there and back, so decide whether that's worth it to you.

There’s some work being done right now on the train route from Rome to Spello, so a portion is switched over to a bus ride making it longer, too. Or, there’s a route up near Cortona and then down to Spello. Either way, it’s not a day trip from Rome.

We visited Spello in mid-October two years ago, while staying at an agriturismo near Spoleto. Several homes had floral displays in window boxes and by the front door, but late Spring and summer probably have more, of that’s your main focus. Some had elaborate statues and other ornamentation that may stay up all year. Many homes have tiles set into the stucco wall, showing what places they received in the flower decorating contest over many years.

It was a Sunday, and there were actually a lot of people, almost all Italians, I think, waiting outside the main church for the service to end. As people exited the church, the absolutely loudest bells in the world rang for a minute or two. There was a small garden to the right of the church that pretty much everyone popped into, but nobody lingered long. I took two or three photos there. Tables at the couple of restaurants open for lunch were almost all full, and we two were able to sit at a 4-top where two French women were already sitting. The hilltown was nice for strolling, some interesting architecture and narrow streets, except for on where pigeons perched high along it, depositing a carpet of droppings for a 70 foot stretch. I hurried along it to avoid getting bombed by any birds. The lower town, outside the ancient gate, was a a decent place where most people seemed to live - not decorated with floral displays, but free parking on the street.

Nearby, Bevagna is a wonderful town, too. Unlike the rest in the area, it’s not a hilltown, but has remnants of ancient Roman and medieval times.

Cortona is a lovely hill top town, and just a tad over an hour from Florence. Been many times in October, and the weather was beautiful, and the town.

Orvieto was my favorite portion of my trip (which included florence, venice and cinque terre).

I agree - spend a night in orvieto on way to florence.

Lucca got booted from my itinerary by teenagers for Cinque Terre (was lovely, and we made it work but not ideal day trip)