Where to Get off the Train?

It may be a little more than a 'jump off the train' stop, I would recommend Lake Como, I stayed in Varenna. Beautiful setting, check. Beautiful village, check. Ferry rides, yes, not sure about bikes. Beautiful gardens. Gorgeous setting. For sure there will be tourists there, but I went in July, and the people didn't bother me. It is easily accessible by train, and once there, you would be on foot.
About the luggage, you keep it with you on the train, and take it with you when you leave the train. Don't bring more than you want to lug around. Read Rick's advice on packing light ;)

Julie... so random. I live in Frisco as well. Thank you for your suggestions.

There is no such thing as a "a small, untouristy, typical Italian village" but train to La Spezia (museum) local bus to Portovenere.

The best Michelangelo works are in the Medici Chapel, not the Academy {Florence)

Venice: San Marco borders on being a waste of time because the dim lighting makes it impossible to see the glorious decorations of the church.. If you must, go mid-late afternoon when there is chance of walking right in rather than spending an hour in line

The best Michelangelo works are in the Medici Chapel, not the Academy
{Florence)

I'll disagree with that. While my favorite "David" is not Michelangelo's, his "Deposition" in the Museo dell'Opera del Duomo (Florence) is a heart-wrenching piece of work as he carved his own likeness into the figure supporting the dead Christ. I found the Medici Chapels overly flamboyant, and Mike's female forms to be weirdly masculine. IMHO, not his best work.

That aside, if your daughter loves art and you only have 10 days, then you will find more in just in Rome, Florence (!!!!!) and Venice to take in than you have time for. Just 2 days in Florence? Not NEARLY enough as it's a gold mine for fabulous Renaissance art!

Truly, you have barely enough time for the three main cities. Many of us would say you really should only go to two of them. If you want to include a smaller town, I recommend that you cut either Florence or Venice. They are both intensely touristy places. As it is, with only about 1-1/2 days in each one, you're likely to be spending most of your time at the same famous sites all the other tourists want to see. Cutting several hours (at the very, very least) out of one of those destinations to stop off somewhere else will only make matters worse.

I'm with acraven on this. 10 days, really 11 nights and 10 days, is a bare minimum for the classic Rome-Florence-Venice trip. Not much time for romantic bike rides in the Tuscan countryside and the quaint agriturismo.

I'd say cut Venice out completely. 2 nights is not enough. Instead, do Rome and Florence with a couple of nights elsewhere in Tuscany. Lucca is a small city with a wide wall surrounding the old city suitable for a nice bike ride. Or Siena. Fly out of Pisa, or do it the other way, into Pisa and out of Rome.

Since you are planning for next year you haven't bought plane tickets yet so I'd fly in to Venice and out of Rome. Or if you decide to cut Venice and just do Florence and Rome, fly in to either.

Venice is sort of a pain to fly out of as there are not many direct flights from there to the US so you have to take a hop to a European hub like Amsterdam to catch your flight to your home airport. That is compounded by having to take water transportation to the airport for an early, early flight. It's just way easier to fly in there, take the water ferry to your hotel area and then fly out of Rome where you can easily get a taxi or train to the airport.

I'd agree with just 10 nights on the ground you'll be pushed to do Venice, Florence and Rome so probably don't have time for a say in a smaller town.

editing to add: If you decide to consider a tour, the Heart of Italy stays in the smaller hill town of Volterra which I found vastly interesting. It is 9 days but I'd want to arrive to Rome at least one day ahead. Ideally I'd suggest arriving 2 nights ahead and staying 1 after in Florence but time is what it is and so is money, lol! This was my first RS tour (started an unfortunate addiction) and I did it with my brother, SIL and their 2 adult sons who were 20 and 25. We had a fabulous time. The early dates have dropped off the "Dates/Prices" list because they have passed but you can call the office to see when they will generally start running these tours.

https://www.ricksteves.com/tours/italy/heart-italy

High speed trains don’t stop in smaller cities. They only stop in Regional capital cities and occasionally some provincial capitals, but none of them are small. Also with only 10 nights you don’t have time for all of that. Stick to the 3 big ones. I also suggest I fly to Venice and return from Rome. The nights allocation should be Venice 3 nights
Florence 3 nights
Rome 4 nights (or at least 3)
If you want small villages eliminate Venice and add nights to Florence. From Florence you can visit several Tuscan towns in day trips.

I believe you should go where you want with the amount of time you have (within reason). Years ago (1996) I had a weekend in London and I went to Scotland for 2 nights, and saw Glasgow and Edinburgh. Too short? Yes. But I wanted to do it not knowing when I would be back. I am so glad I did, because I still have not been back.
So, if you want to do 3 cities plus a more scenic smaller one, this is what I would do:

Day 1-2 Rome, and see what you can, Colosseum, Vatican, Trevi Fountain, Pantheon.
Day 3 morning in Rome, then train to Florence (1/2 day)
Day 4-5 Florence
Day 5 train to Lake Como (less than 1/2 day, and a pretty ride)
Day 6 Varenna
Day 7 train to Venice (1/2 day)
Day 8-9 Venice

Another smaller town option is Verona (where Juliet's balcony is, but that is a waste of time). Easy train access on the way to Venice.

"The best Michelangelo works are in the Medici Chapel, not the Academy {Florence)".

Obviously people differ, but I think this is some of the worst of Michelangelo. You can see that he never actually saw a naked woman as his female figures are ridiculously inaccurate. And the chapel is garish. The Davis and the slaves in Academia are among his best. I think the two greatest Michelangelo's are in Rome -- the Moses and the Pieta which is now alas displayed badly as it was attacked a number of years ago by a loon with a hammer and is now distant and under glass.

With this much time I would choose two places and that would give you a night to go to a smaller town. Small picturesque Italian towns are entirely tourist driven; there is no real economy besides tourism in such places, but they are gorgeous. With 10 days you don't have time to do justice to 4 places especially places like Rome and Florence with such depth of artistic heritage.

Keep in mind, with a 10 Day trip you actually only have 8 nights. The first day you travel and arrive the next day. You also leave on day 10 so that's not a viable day.

If you can expand you're trip to 14 days, 12 nights what you're dreaming of is possible.

3 nights Venice. ( first day jet lagged) 4-5 nights Florence (including 2 day trips) and 4-5 nights Rome. ( easy day trip from here too)