Some Serious Help Needed with Itinerary

What month will the trip occur?
Italy is like a smorgasbord so it is hard to relate to not being to pick out anything! But I understand being overwhelmed. Here are some ideas that will hopefully identify what you don't want if not what you do want.

After Cinque Terre, you could go to Genoa (though I would upgrade from a hostel there) or a different smaller riviera town like Camogli, Rapallo, or northern Tuscan towns like Sarzana, Lucca, Pistoia. I'd be scanning Liguria and Tuscany books for this week. You'd be well placed to get to Florence for your flight. The Ligurian coast is well served by train.
From Milan, I'd head to Emilia-Romagna--Bologna, Parma, etc. This area would be convenient for day trips by train and put you again in position to easily reach Pisa.

It certainly isn't easy to be a mom, want to be with daughter as much as possible and yet still not spend your days twiddling your thumbs waiting for her to finish class.
If she has just arrived, then does she know her scheduling enough to know what amount of time she needs to commit to homework? Of course our kids are going to say "I want to spend time with you when I am not in class" but how realistic is that - really? Maybe 1 or 2 afternoons a week? Personally, I would plan some overnights for myself during the week ensuring there was a day or two in Florence to make plans with her.
Your last Friday/Saturday is cramped with that Sunday noon flight, so maybe Siena, Arezzo, or something just an hour or two away by train.
I don't know how into gardens you and/or your daughter are, but there are loads in Italy and because they are mostly structural and evergreen, season won't be too advanced into Fall for them. You could review what are close to Florence (there are a few) to use as some 'themes' for your afternoon trips. Also, there is a website 'atlas obscura' that lists obscure things in areas. She might get a kick out of seeing things off the beaten track or funky close to Florence.
It might also help to know exact dates so we can see if there are Italian statutory holidays that might mess up your plans.

I arrive October 16.

I figured if I'm staying in say, Sienna, she can take a train to spend the night with me after class then head back to Florence in the morning.

She thinks I should spend all my time staying with her for free in Florence and doing day trips. (Saving my money so we can splurge in Morocco.) I would like to do an Agriturismo in Tuscany though.

All the car rental places are closed when I arrive in Milan BGY. And there is only 1 bus still running to Milan Central Station. Trying to figure out what to do from there! :( I'd like to head East from there.

I arrive October 16.
That is soon and you need to get accommodations sorted!

I figured if I'm staying in say, Sienna, she can take a train to spend
the night with me after class then head back to Florence in the
morning. She thinks I should spend all my time staying with her for
free in Florence and doing day trips. (Saving my money so we can
splurge in Morocco.) I would like to do an Agriturismo in Tuscany
though.
I was answering as if you would do your own thing during the week. Doing day trips from Florence would certainly simplify things, and limiting your choices to places within your daughter's reach from Florence would also help you make decisions. Do you have a good Tuscany book that details which places are within the travel distance she would prefer?

All the car rental places are closed when I arrive in Milan BGY. And
there is only 1 bus still running to Milan Central Station. Trying to
figure out what to do from there! :( I'd like to head East from there.
I'd just stay that night in Bergamo. Then Sunday your daughter can head home if she is on the same flight, and you can head east, toward Verona perhaps?

but she has school Monday through Friday 9am - 12pm

First, some clarification is in order. Folks commonly use 12pm when they mean noon, or 12am. I'm assuming you mean she has morning classes and her afternoons are free. Using a 24 hour clock like Europeans and the military sure prevents misunderstandings (1200 = noon, 2400 = midnight).

On the days your daughter is free after class, there are a number of short trips to places near Florence you can take using public transportation. I would assign your daughter to scout out the possibilities and you and her work out the details together before you leave. For instance, Greve is an easy and inexpensive 40 minute bus ride from Florence. Let's say you could leave at 1300 after your daughter's class. That puts you in Greve at 1345. You could grab a quick lunch and explore the town, which would take only a few hours. Then, according to the last bus heading back to Florence, you could either had an early (1800) dinner in one of the many choices in Greve or head back to Florence and have a later dinner there.

You could also explore a winery tour leaving from Florence that includes a late afternoon winery tour with a food and wine tasting dinner.

Friday leave at 12pm: Cinque Terra? (Early before the weather gets too bad?)'

Huh? I'm not sure I understand the correlation between the weather and time of day. It sounds like you'll be there in mid-October, which should be before the winter storms, but there's no guarantee. Have you made reservations yet? I don't know how availability runs then. I think you have a better than average chance of good weather, but if it is cold and rainy, unless you like to be out in the elements, there's not a lot to do.

I meant visit Cinque Terra early in the trip vs the end. In hopes of better weather around Oct 18 vs Nov 3.
I have nothing booked anywhere yet! EEK!!!!!!

Is your daughter's apartment really comfortable enough for two people? If so, I vote with her that you stay with her and save money. Two years ago I spent 5 weeks in Florence with only 2 day trips and there was plenty to do. And I'd already seen most of the major things to see on a previous trip!

It is so easy to do day trips by yourself or a weekend trip with your daughter (like to Siena or to stay at an agriturismo) using Florence as your base. I think you would struggle with both transportation and accommodations (and your suitcase!) if you try to stay in too many locations during your 8 days and it will eat up your precious time.

I have nothing booked anywhere yet! EEK!!!!!!

That leaves you with two courses of action regarding CT. You can go ahead and see if you can find something and make a reservation, counting on the weather being good. I agree, there's a better chance of good weather at the beginning of the trip than the end, but you may have a better chance of getting a nice booking with more lead time.

The other course is to not book. If the weather is ugly when you get there, make alternate plans and try to go at the end of the trip. I don't know how successful you'll be able to find something last minute, though. Things have changed over the years, especially in over-touristed areas like CT. The good places are often booked up months in advance. Out of curiosity I looked up a nice villa near the town of Radda for next Spring. It was booked up for Spring and all the way through summer.

I did a quick check on Vernazza for your dates and right now there are either few rooms in the 100-120 euro range or rooms in the 230+ euro range.

Bergamo is a worthwhile destination, so definitely take advantage of this opportunity to see it. The historic upper town is the place to stay. There's rail service from the town of Bergamo to Milan, from which you can travel on to wherever you decide to go.

I'd immediately buy a guidebook with comprehensive coverage of Tuscany. The easiest/cheapest thing to do is to see some of the lovely places you can visit while crashing with your daughter. Without the pressure of time, you can spend a day going to a place San Gimignano, not trying to squeeze in visits to two or three other places the same day. Volterra, Lucca and Siena are other good options. You might consider taking a small-group tour one day to some smaller towns that wouldn't be convenient to visit via train and bus.

I like Bologna a lot, and its large historic area is heavily arcaded, offering considerable weather protection on bad days. The tourist office offers walking tours. A day-trip to Bologna would be a very full day, but you could also spend a chunk of days in Bologna, seeing the city and taking day-trips. Weekday hotel rates in Bologna are not particularly cheap, however.

For trips involving express trains (including Florence-Bologna and possibly the trip south from Milan), you can save quite a lot of money on non-refundable, non-changeable tickets if there are any still available for your travel dates. For closer and smaller destinations you'll be on regional trains and needn't worry about planning in advance.

My two top priorities for the time in Morocco would be Fes and Marrakech. Casablanca is a modern city and totally skippable.

I booked Cinque Terra for the first weekend. Now I still have to figure out the rest of my time. I'm just not sure her roommates would want me around that often.

Personally I really think you can be flexible. It is only you travelling mid October and into November. And you have your daughter's place for back-up. I would suggest towns like Lucca, Volterra and/or Sienna for your first week. You'll be closer to her, and if you don't find the accomodation you want you can train back in the evening, and if you do she can train to join you.

The second chunk you might want a little further afield, or wait and decide based on weather. Something like Verona, Bologna and back to Florence, appeals to me. ( Good Italian food once it is getting colder!) And all fairly easily done by train.

Since your daughter has a lot of free time while she's in school, I'd assume that she's been to most of the places you could visit together on school days. Or if she hasn't had time yet before your visit, she will afterward. So do you want to spend all your mornings in Florence to have half-days with your daughter (assuming she has all that free time with study responsibilities), or do you want to use some of that time to go off on your own for 2-4 days while she's in school?

Staying anywhere but Florence during the week, means one of you will be commuting. It makes more sense for you to be the commuter. If you're in Siena, for instance, it will take her as much as an hour and a half to get to Siena (one hour just on the bus). And you can sleep in after a late night. Florence also makes the most sense because it has the best transportation connections.

As for hostels . . . are you willing to stay in a dorm room? Single rooms are booked well in advance and you may not find any by this time.

The CT is problematic not just because of weather, but also because of overcrowding. You could go to Assisi or Orvieto or Ravenna for a weekend. All are great places for a 2-night stay. Remember you'll want to be back in Florence Sunday night so your daughter can get to school in the morning.

We visited our daughter when she was in Granada Spain for a week. We stayed in Granada and took a day trip one day during the week with her and then went to Sevilla for the weekend. I would not have wanted to stay in a different town than she was in. We had more time than she and this way we maximized our time with her. Now we did not stay with her both because there were two of us but also because she had a room in a private home not an apartment.

We saw the trip as primarily seeing her and anything else was gravy. But it really is fun to see a city through the eyes of your child who is living there.

Maybe stay the first couple nights with her and then get a place of your own after you return from your weekend jaunt? Personally, I would stay in Florence and day trip to other places.

Beth

Thank you!! I appreciate all the advice! I think I will take it! She hasn't done much because she is on a tight budget. So she is definitely looking forward to me coming and splurging on her! I think I will enjoy Florence and my time with her. She has her own room with a full size bed that we can share. She is looking forward to me coming and helping her figure out ways to cook on a budget. I think it will be fun to help her find local markets and delis.

Does the RS Florence book have more details than the Italy book?

Click on the guidebook in the RS shop and then click on "Is This the Right Book for Me"