Taking Mother and Daughter to Italy in October HOPEFULLY to find NONNA

It's difficult to say what is a safe time to book entries to high-demand sights, which all that you list are. You won't want to do it unnecessarily early for fear of losing your money if the trip unravels. I'd suggest you start looking at the websites now to check on ticket availability for dates in the immediate future. Is there availability for tomorrow? Two days from now? Three days? A week? By monitoring current availability you should be able to develop a feel for how far in advance you need to buy.

Special tours (lower level of Coloseum, Doge's Palace Secret Itineraries Tour, Vatican Scavi, probably early access to the Vatican) have in the past sold out quite early, so you need to decide whether you want any of those.

I can tell you that even before COVID-19, Scrovegni Chapel tickets had to be purchased at least one day ahead of time. I believe they've cut the number of people allowed in at one time, so 24 hours in advance might not be sufficient now; it was fine for me in summer 2015.

The high-speed train tickets will probably cost you less if you buy them as soon as they go on sale. However, you again have the risk of losing that money if the trip cannot be completed as planned. It's a judgement call. I'd look at how much I stood to save and decide whether it was worth the risk. The way things are going now, your outbound flight could easily be rescheduled, causing you to need to shift the dates of your hotel bookings and train trips.

Most likely you won’t get much sleep on your flight so stay in Venice for two nights and then take a direct train from Venezia Santa Lucia station to Padua (30-minutes). The nearest car rental agency seems to be less than a mile from Pauda's city center: https://www.expedia.com/carsearch?dagv=1&subm=1&fdrp=0&rfrr=TG.LP.SrchWzd.Car&locn=City+Center+Padova&loc2=&date1=10%2F01%2F2021&time1=1030AM&date2=10%2F02%2F2021&time2=1030AM&kind=1.
I also recommend reserving tickets before leaving home. I would skip the Cinque Terre because it’s not a day trip from Florence.

Do I reserve high speed train ahead or is it necessary? (schedule not online until 6 weeks? before)
Schedules should be on line now. Schedules change in June and Dec but the changes are often very small. Tickets should be available roughly six months in advance. There are three levels of fares -- Super Econ, Economy, and Base. Fares do not change daily like airlines. For SE, E tickets the number of tickets available per train/time are fixed and once sold out there are no more. Those tickets come with restrictions mostly related to no change, no refund. Base fare is always available. Trains rarely sell out unless it is a special holiday or some event. But there are lots of trains all day long. The ONLY reason to buy in advance is to take advantage of any discount ticket that might be available. Trains are cheap in Italy and the base fare is very reasonable.

How far in advance to reserve ? Scrovegni, Vatican Museum, Colosseum, Uffizi, Etc. ? How crowded now? Who knows these days ??? Prior experience doesn't count right now.

Would love to go to Cinque Terre for a day (without mom) from Florence, but maybe crazy? Too far. Too much time on the train. CT is an area - five villages so you would need to pick a village. Save it for the next trip.

I prefered staying in Vicenza to Padova, but different strokes for different strokes....

At least try to get a walk through Vicenza - it is quite special.

I agree if you can to do the jetlag recovery in Venice,

If you have a car Bassano del Grappa is quite an experience too....

Can you tell that I miss that area. Last time I stayed in Vicenza I was there 10 days and didn't get to everything around. But then I also do Venice a week at a time, and with your Mom along I'm sure you only have so many days to spread everything onto.

I agree with the others about a day trip to Cinque Terre.

"I have an Italian genealogist I have been emailing and arranged one day tour of town."

I have no answers for your questions but I would love to know how this turns out for you. Contemplating trying to find something like this to see where the GGparents came from north of Milan.

I second Nigel’s recommendation of a visit to Bassano del Grappa, beautiful with an Alpine feel. We loved the Veneto and made a dedicated trip to it. Vicenza is very worthwhile.

Pat,
We stayed in Padua for 6 nights in October, 2019, around the corner from the Basilica.
I suspect that your Mom will enjoy the Basilica.
Daily mass and usually an English speaking priest available for confession.
We also enjoyed the botanical gardens, Scrovegni (book ahead), walking the streets, and the food.
We visited several nearby towns by train, including Vicenza. The trains are so easy and comfortable. It wasn’t a problem to book the train at the last minute.
If you have time , spend a few hours in Vicenza.
It is a lovely town.
Good luck!

We stayed in Padua for 9 nights in September 2019 and at that time you could book special back-to-back evening tickets for the Scrovegni Chapel that allowed us to stay inside the chapel for 40 minutes (after the required 15 minutes of watching a little movie and getting de-humidified). I had visited the chapel almost exactly 50 years before while on an art history tour --- you could just stroll in then and spend as much time as you wanted to. But it's better now that they are trying to preserve the paintings and also the paintings were restored at some point during those 50 years. Anyway, it's my favorite artwork in the world and there is no way each fresco scene can be seen in the 15 minutes of a single booking.

Check to see if any high speed train really gets you some place THAT much faster to make the anxiety over possibly missing it and then forfeiting the price if you do miss it. We've pretty much given up on taking them. So much more relaxing and flexible to just buy a regular ticket at the train station.

I know Velo D'Astico as I lived in Vicenza many years and our favorite summer swimming spot was the Contra Pria in Arsiero, right next to Velo D'Astico. It is a beautiful area and as others have said, I would try to include Vicenza and Bassano in your trip since you'll be right there. Marostica is a sight to see as well, with the old walls up the mountain still intact. Good luck on your trip, it sounds amazing!

Check to see if any high speed train really gets you some place THAT much faster to make the anxiety over possibly missing it and then forfeiting the price if you do miss it.

One example would be Bologna to Florence. It is possible to take an occasional Regional, but not directly. You need to go well off your straight route and change at Prato (or Pistoia, I don't remember, I'm writing this from memory) and the connection isn't a quick one, and you don't go into Firenze SMN, you go to the through station out of town (Campo di Marte I think) where you need yet another train for the hop to SMN.

It wasn't much cheaper than the direct nonstop Freccia between Bologna and Florence - and way slower and less comfortable.

voice of experience

Thanks to all for the great advice!

Rik- so glad to hear of someone that knows Velo D’Astico!

I am following Rick’s Italy forum daily to get an idea how this new world of travel needs to be navigated.

Praying we will go September 30!

Your itinerary sounds great. I think others might have missed that you are flying business class from ORD-FRA. You'll get plenty of sleep, and even if you don't, it's only a 45 minute drive from VCE to Padua.