8 days free after leaving Venice and before going to Rome

From Venice ( if you choose not to add one more night there) you could go to CT and spend two nights there, then on to Florence/Siena for 3 nights each and do day trips to places of where ever your interests take you.

Same day train to Rome from Siena or Florence only slightly more difficult to do than finding a glass of wine in Italy. :)

You can do very well sticking to places easily visited on the train. Florence, Siena, Orvieto, Lucca. Definitely try and spend a few days in a smaller city. Siena might not be a break, it was mobbed when I was there in early November 2016, but I think it had to do with the fact that Nov 1 was All Saints Day. Cinque Terre is great too, could be a zoo though based upon what I have read of late (my wife and visited as a day trip from Lucca in 2007). Looks the travel logistics but after four trips to Italy, I regret not having visited Assisi. Also, Padua and Verona nearer to Venice (I have not visited those, I just think they look worthwhile based upon my research). Rome is worth three full days (four nights) minimum, and an extra day would be better. Trains in Italy are easy and relatively cheap. You might have to change trains once or twice to get from Siena to Rome, but it's not as hard as it might seem. Orvieto to Rome is a snap. I encourage you to push the "easy" button and go to places that are logical and easy to get to, you really cannot go wrong in Italy. Except I really, really encourage you to go to Orvieto, it's on the way to Rome and such a magical small city. I never made it there until my fourth trip and loved it.

The Cinque Terre wasn't quite a zoo last May when I visited (third time) though it sure wasn't empty. It can depend which day you visit - if cruise ships are docked nearby there will be more people.

Visiting somewhere in the beautiful Italian Riviera is a great idea - whether it's the Cinque Terre or somewhere else like Santa Margherita Ligure or Camogli or Rapallo or elsewhere. Frequent trains run up and down the riviera making it easy to do day trips all around to lots of places, depending on the time you have.

If you do wind up training directly from Venice to Florence, your train will pass through Bologna. One thought might be to stop there for a few hours en route and have a meal. Bologna isn't the most charming town in Italy, but the food is outstanding. and it's certainly worth exploring the old center too, even if you don't spend a night there. You can leave your bags at the train station, but you'll need two train tickets - you can't just hop off hop on.

To check rail schedules I prefer the Deutsche Bahn website. Cinque Terre is the name of an area, not a town, so you'll need to specify one of the town names. Until you decide where to stay, you can just use Vernazza.

When you progress to caring about rail fares, you'll need to look at TrenItalia.com or trainline.eu. TrenItalia is picky about city names: You have to use the Italian form, so it's Venezia, Firenze and Roma. Fares for the fast trains Venice-Florence, Florence to Rome, and possibly some short parts of other trips) will usually be cheaper if purchased early, because only a certain number of promotional-fare tickets are available. The cheapest tickets are non-refundable and non-changeable, so be sure you know what your schedule is before you buy anything.

Italy is wonderful, and all the places mentioned are great. I like your plan not to move to a new hotel every night or two. That's very tiring and reduces the amount of time you actually have to see Italy.

Hello - You will have a great trip. Truly you can't go wrong in Italy! I highly recommend a couple days in Cinque Terre; remember it is 5 hill towns in the region of CT. My husband was sick with a sinus infection when we visited CT so we just rode the train between each town and got off for a look around. It is possible to hike between the towns if you have lots of time. Also, we loved visiting the Banfi estate vineyards. https://castellobanfi.com/en/hospitality/winery-visits.php We splurged for the lunch and tour; reservations required. Castello Banfi is near the town of Montalcino. Another Tuscan town we enjoyed was Montepulciano. One of the reviewers regretted not seeing Assisi. We did visit Assisi and it was one of my favorite day trips. The trains are quite easy in Italy as long as you remember to validate your tickets in the little yellow box at the track. We forgot to do that and nearly got kicked off in Pisa. A kindly Italian talked to the conductor who allowed us to continue our trip to the Cinque Terre. Our son did all the driving while we were in Tuscany; it can be challenging but it is a good way to get around the Tuscany region. The trains are good for going distances. Have fun! Safe travels!

I thank all of your for your suggestions and ideas! We have booked Florence for 4 days after our 3 night Venice stay, we will be right in the city centre in both cities, and then are moving to Fiesole for 4 days of quiet time at Residence Fiesole. Will not undertake a car rental this first trip to keep it simple. I am hoping we can pick up some day tours from here, or not far from here, and maybe do some walking or biking in the area as well. Again, thank you!
Ciao!

I've never been to Fiesole, but I'd suggest investigating your side-trip options ahead of time so you know how doable they are from Fiesole. Fiesole has no train station, so many (maybe all) of your side-trips will require that you first get to the Fiesole bus station, then take a bus to Florence, then switch to a train or a second bus to reach your destination. It will be simpler to do the most commonly recommended side-trips (Siena and Lucca) while you're staying in Florence.

Fiesole is a small town on a hill overlooking Florence (nice views of the city below). AFAIK you'll have to take the bus from there to the train station for any day trips in Tuscany, either by bus or train. Consider staying in Fiesole and busing to Florence for sightseeing and maybe dinners, then staying in Siena to day trip to other places in Tuscany.

Fiesole is a beautiful small town on the outskirts of Florence, it is a quick bus ride from Florence and easily visited while you are staying there. I would suggest after Florence to Siena or Lucca, where again you could take trains or buses to the area. You could then take a quick regional train to Rome, avoiding driving.