Florence 3 Day Plan - Help

A Food tour might be fun for that first night. We did one with Walks of Italy and it was great.

My first thoughts are good luck! Have done a tour like this with a group of 9, it’s like Herding Cats!

You have too much planned, I personally and regret to say this, would drop the Uffizi. Too much visual overload unless really interested in art. Use this day to do a walking tour of Florence
Then take the bus #12 or #13 to Piazzale Michelangelo.

You Really need to rethink the night train.
Look at a budget flight from Florence-Munich.
You’ll get there at the same time if you leave the next morning and it will NOT take 10 hours.

Vueling
11:00 AM
FLR

12:20 PM
MUC
$49
Nonstop1 hr 20 min

Hope this is helpful.

Edit: agree w/ Poster below. Basilica of San Miniato is one of the best in Tuscany, stairs may be a killer for your mom.

https://florencetips.com/san_miniato_al_monte.html

If you do go up to Piazzale Michelangelo, in addition to the sunset, you should take a little time to visit the church of S. Miniato.

It seems to me that what you are actually saying is that you have two nights in Florence. On our first trip to Italy, we came from Rome on a train in the early afternoon, spent the next day in Florence and left in the afternoon of the 3rd day...two nights. One of my biggest regrets was not spending enough time in Florence. For our next trip, I've planned four night and maaaaybeee, we'll make it outside of the city. I'm also sorry we took a taxi from our hotel after we had kinda found our footing. It was very expensive and we could have done it ourselves to the train station.

I'd be wary of micromanaging the group activities. Been there, done that. When you aren't a paid tour leader, the whole thing is about negotiations and moving surly, footsore people about. Most groups of people have different levels of activities and energy. Is it multi-generational? With 8 people, it might be difficult to find suitable seating in a restaurant unless you have a reservation. I believe the market food court had group tables and food could be ordered from different vendors. That would tick a lot of boxes.

Each day, I'd book ONE local activity to shape the day to get people out and about. If your people are anything like my people, they want a little structure but not much. Afterwards, people could split up for their own explorations. I'd definitely take everybody to see David. It's a small, manageable museum that needs timed tickets. Maybe you go to the Duomo and climb the bell tower or not. Kids could spent a substantial amount of time riding the carousel, chasing pigeons and eating gelato. Walking over Ponte Vecchio to Oltarno and watching the sunset could be an entire afternoon's adventure. We actually took a free city tour our first afternoon there. It was fun and even with a tip, the price was right. You don't want to pay for things that people may not want to or feel forced to do.

There may be those in your group who would enjoy the Uffizi. Others might like buying shoes and leather products. (Everybody loved the wallets I brought home.) It's a small town. You can split up and regroup pretty easily. To me, the important part of Florence is enjoying the ambiance. I think it is important to breathe the air and enjoy the light. I perceive it to be a pretty safe place. For a teen, it might be a life-changing experience to wander alone through the Duomo or sample all the gelato their heart desires. Give them a sketchbook. Maybe they save their pocket money before the trip and buy the leather jacket that lasts a lifetime.

Leaving on a late train with a big group after having checked out earlier from your accommodations sounds particularly hellish. I've done this and it just gets really hard with a lot of people. Kids need naps. Folks want showers before a night train. People are bored or don't want to schlep stuff.

Good luck with the planning. Make sure to include other opinions and make sure the expectations are known. Remember, the less control you take and the more responsibility you give to others for their activities, the better chance there is for YOU to have a good time.

I'm extremely concerned about the plan for the night train. I'm assuming it isn't the case that all your travelers have night-train experience. Although some folks handle night trains just fine, I believe in most cases those are folks who can sleep anywhere, under nearly any conditions. I figure the odds that any group of eight people will be comprised only of people like that are vanishingly small. Some of your people are going to toss and turn all night and not be productive sightseers the next day. They'll either have to crash in their hotel rooms (which, of course, will probably not be available to them for many hours after you arrive) or drag themselves around, possibly making the rest of you unhappy. If they do crash for a major part of the day you arrive in Munich, they're likely to be off kilter and off their sleep schedule that night.

A major issue with most night trains is that they are far from non-stop. The one you are contemplating makes these stops:

11:45 PM Bolzano
3:25 AM Tarvisio
4:29 AM Villach
5:49 AM Schwarzach-St. Veit
7:01 AM Salzburg
Unknown time Rosenheim

Each stop comes with braking, station noise and then acceleration. I don't think many people can sleep through that, and it's going to happen at least five times when people would want to be sleeping.

"We're catching the OBB NightJet train for Munich at 10:30pm"

We've done this train on several occasions, and never really had sleeping issues. We did it more for the experience. I think only once we were a little restless, but the kids were out like a light. The beds will be pre-made when you board, as it is late at night and they expect you to be ready for bed. You don't mention how your group will be set up in the sleepers. Will you have three-four to a room or doubles? With the bunks, only the top person has enough room to semi sit up. The other bunks do not allow enough space between bed to top of the bunk above to sit up, so be prepared to literally go to sleep once boarding. In the mornings, they give you a boxed breakfast around 45 minutes before arrival. Depending on which accommodations you choose, the bathroom will be down the hall from the rooms, or the superior double rooms can have a bath in the room. We've had both. The stops really didn't wake us. What time of year are you going?

An earlier poster mentioned flying which is probably an easier option. With Vueling, it is a nice airline, but depending on your ticketing options, you will pay extra for pre-selected seat and luggage fees. Do the math. Also, you will find that "hanging around" until 10:30 can get boring unless you can have a late checkout at the Air BnB or take a late dinner to fill your time. You will not have meal options on the train. Take snacks and drinks with you on the train.