Italy Itinerary

Unless you deal well with jetlag and you sleep well on planes I would consider an extra day in Venice. By the time you get there and check-in it'll be close to 7, unless you get there early and your hotel is on the mainland. I would be exhausted for the whole time I was there. There's a lot to do there and imo the best part is just walking around, but it's not always easy walking.

If it works transportation wise I would look at Venice, CT, Florence, Siena, Rome. That way you won't be backtracking. CT to Rome would be a long travel day. Eh, just looked, train from CT to Rome is only around 5 hours so not that long.

I would go with the longer itinerary no matter what you decide though, you're already there, you've already paid for the flight so what's an extra couple nights?

I would suggest you take away days 7,8,9 from Florence and head for the Tuscan countryside. That would mean staying in an agriturismo with a rental car and touring around to the different hilltowns. That would include Siena.

Pisa is a very popular flight destination, but most skip going into the city as it's just The Tower and a beautiful Duomo there.

I'd be hesitant to hit the C-T in October ;as it's more of a summer place. It might be a good time to hit Lake Como and the Swiss border towns, however. They're less than an hour north of Milan.

And never cut your time in Rome short as it's such an important travel city. You're just so fortunate to have so much time that you can choose from many alternative stops.

Congratulations on your upcoming trip! 2020…. : (

First, yes to adding the two extra days.

A possible route for your 20 vacation days in Italy, not counting flying
Venice (Venezia) - 4 nights
(Do a day trip out to Burano - others, if interested)
1 hr train to Verona - 2 nights, lovely city!
4.5 hrs trains to Cinque Terre (Monterosso) - 2 nights
2.5 hrs trains to Florence (Firenze) - 4 nights
1 hr bus to Siena - the bus will leave you off in a convenient location. - 3 nights
(Schedule some wine tours that take you to Montepulciano, etc.)
Bus and/or train combo to Rome (Roma) - 5 nights
(Day trip to Orvieto - 1.5 hrs by train from Rome)

I’ve placed the Italian name of the cities in parenthesis, so you can look up travel times & options on www.trenitalia.com or their app

I’ll attach my last trip report that had some fun activities in Florence. I especially recommend the pasta cooking class!
https://community.ricksteves.com/travel-forum/trip-reports/mother-adult-daughter-italy-trip-aug-sept-2022

Venice: On arrival day settle in at your hotel, freshen up then treat yourself to a nice meal to end the day and the next day hit the ground running. I would spend the first day in Venice seeing the sights. That evening at twilight, hop on a vaporetto (water bus) from the train station or San Marco Square or even further so you can see the palaces that line the Grand Canal fully illuminated and not the erosion on the exterior. The experience took me back in time. I’ve done it twice and will do it again if I return. The following day get, lost. I feel three nights in Venice is enough.
Florence: Take a direct train from the Venice train station to Florence’s (Firenze) S.M. Novella station: https://www.trenitalia.com/en.html. Also, buy tickets for the Uffizi Gallery two-months out to guarantee a reservation. You need three nights in Florence by itself. If you add day trips add a night per day trip. Since you would like to visit Siena, Verona and Bologna sleep in Florence six nights.
Siena: I don’t recommend sleeping in Siena unless you rent a car so you can explore the Tuscan countryside. I do prefer Siena at night more so than as a day trip, but it will be easier as a day trip when it comes to logistics since you are visiting the Cinque Terre. Do go to Siena but as a day trip from Florence by direct bus that will drop you off outside the old town (1h 15m).
Pisa: I like this plan and you can store your bags at the Pisa train station so you can see the tower and the Field of Miracles. This is a good stop since you must switch trains to get to the Cinque Terre. The direct train from Florence’s S.M. Novella station to Pisa takes 1h.
Cinque Terre: Monterosso al Mare will be the easiest place to stay because it involves no transfers if coming from Pisa (1h 15m). If you don’t hike you only need two nights here. If you do hike add a night per hike. Note: the hikes here are not easy.
Rome: you will have to connect from Monterosso to get to Rome’s (Roma) Termini station (4h 30m). Be prepared to carry your luggage up and down stairs so pack light and do laundry often. From Roma Termini you can take a train to Rome’s Fiumicino Aeroporto (45m).

I like your 22 day plan. You could add the extra day to Venice to see Verona. It's a wonderful city and you have roots there. I would leave the rest of your itinerary as is. It's a nice slow pace with time to stop and smell the roses. Many day trips you can take from your extra days in Florence. Pisa, Lucca or Bologna. From Rome you can always take a day trip to Orvieto if you find yourselves with an extra day there.

Thank you everyone for your input and response. We appreciate it so much! We are going for the 22 days! I think the last thing we are really on the fence about is the order of travel… original thought has been Venice>Florence>Siena>Cinque>Rome we are flexible with all the middle plans except Venice and Rome as that’s where flights will arrive/depart. Someone mentioned that we do Cinque after Florence then down to Siena and onto Rome… would that make more sense as far as travel times to places are concerned? I know the travel from CT to Rome is far.

If you are interested in Verona I think you might consider spending 2 nights there because there is so much to see. I’ve stayed there twice, for 2 nights and for 4 nights. My favorite place I’ve stayed in all my travels is an agriturismo just outside Siena and you could have that experience without a car. Friends stayed there upon my recommendation and they walked into town. You could also easily take a taxi. If you really want to explore the smaller towns in Tuscany a car is the best way to do it. The agriturismo serves dinner (optional) and it’s the best food I’ve had in the 6 weeks I’ve spent in Italy over 2 trips. I would eat there every night. If you’re interested just PM me for more information.

We did the opposite itinerary, starting in Rome, then Siena (agriturismo), Florence, one night Lucca, then stopped in Pisa on our way to the CT. We stayed in Vernazza and we didn’t have to go to Monterosso first on the train, so no backtracking. From Vernazza we went to Lake Como, Venice then Verona since we were going to Germany from there. You might want to play around with train schedules to see if you should go to Florence and Siena before the CT or if it would be better to go to the CT before those places.

You've got a lot of good suggestions above. I just wanted to congratulate you for resisting the all-too-common approach of "I've got 20 days and I want to see 19 places" travel planning. You'll enjoy your trip much more staying longer in each city, doing day trips as you like. That said, I'd encourage you not to shortchange Venice, Florence and Rome with too many day trips. They are gems on their own and deserve as much time as you can give them.

A direct train from Venice to Verona’s Porta Nuova station takes 1h 30m. The train from Florence’s S.M. Novella station takes 1h 45m. I agree with Joyce about going to Verona from Venice.
The problem with the Cinque Terre is it’s an outlier. You can take a train from Monterosso to Siena that will require multiple transfers but it can be done in 3h 15m. There are direct buses from Siena to Rome (2h 45m) but no direct trains.