Italian trip over Christmas vaca

Just to make sure, although you likely already know this, you’ll need to bring the written consent of both her parents to travel with her internationally, ideally notarized and including authorization to make medical decisions in case of emergency.

Personally think it is too ambitious. You really have not allowed for travel days. You lose at least a half day if not more when changing locations. That could be maybe three days with your plan. You id 12 days in location and assuming a arrival and departure day, gets you to 14 days. In my opinion. -- too much. And you lose Christmas day and most of Christmas eve.

I would consider skipping Venice since it will be cold, damp, and somewhat dreary at that time. I would fly into Milan and come home from Rome. You could do three days, including arrival, in Milan, Is there a reason for Medisimo? I am not familiar with Medisimo so am reluctant to have an opinion as to a visit. You need to carefully plan for Christmas day as little will be open. A few restaurants may be open but don't plan on it.

Will wait to see your response before offering more suggestions.

I would take a much closer look at your itinerary with particular attention to your travel days and how long each connection will take (door to door) and by which route. Especially around a stay in Madesimo (note the correct spelling) . It does not have a train station and getting there and onwards will involve a combination of trains and buses. Going from there will take anywhere from 6-7+ hours to Florence or Venice. Essentially a whole day. Spending only one day in Venice (given the amount of time it takes to get there) seems a waste of time. And remember how very short the daylight hours will be. Note closures or reduced hours from Christmas Eve through St Stephen's day.

We have, what I hope are, the needed documents.
Granddaughter asked for some snow days and looking around at the various choices, the Madesimo slopes say they open in November and the Christmas season is crowded everywhere so we’re hoping she can have some ski/toboggan for a few days before the crowds. We are assuming some snow and no crowds, and it is not far from Milan. Also, we have tried to fit in travel days. For instance, about three hours from Milan to Madesimo, then 2 full days in Madesimo, and about 5 hours from Madesimo to Venice, then one full day in Venice, then about three hours to Florence, after which 3 full days in Florence. Then about 4 hours to Rome on Dec 26, after which 5 full days in Rome. So the days listed in original do not include the travel days. Of course, the best laid plans of mice and men …
We’ve thought about eliminating Venice, and I know one should plan with returning in mind, but we also are thinking this could be the unique opportunity.
Thank you for your comments!

There's a Santa Claus regatta in Venice, most likely on Sunday December 20. If I understood your itinerary, you'll only be there on the 19th, but if that's something you think your granddaughter would like, maybe it's worth adjusting your plans a bit?

This sounds ambitious, but I haven't looked closely like you have at the trains.

Florence, after which 3 full days in Florence. Then about 4 hours to
Rome on Dec 26

Christmas Eve expect quite a bit to close early, not sure what are your plans but I would book ahead or plan dinner that day, and what to do on Dec 25th as well. So if you wanted to see anything that requires pre-booking, like the Academia, book ahead. Frankly Dec 24th might actually be a tiny bit quieter, with Italians perhaps focused on getting ready for the evening, who knows? Just so you're aware, Dec 26th is also a national holiday in Italy, but in central Rome we found lots open, especially restaurants filled with Italians enjoying a day off. I would happily skip Milan as you don't have enough time to enjoy much there, give yourself a bit more breathing room. Hope you have a great trip!!

Thank you all for your ideas. The Venetian regatta is appealing, we’ll have to think through that carefully. And Sandancisco made me realize that my “3 full days” in Florence is a bit exaggerated. We’ll enjoy walking and wandering but there is really just two days when museums will be open. Per internet search, it appears that the hours for at least some of the sites should be enough on Dec 24. It will be the meals that we’ll have to plan for. There seems to be some restaurants offering fixed menus. And I hate to not use Dec 26 as a travel day (or the 25th) because things are more generally closed those days. But December 25 is likely to be wholly memorable if we stay in Florence. There is still much to look into as we plan, especially the timing of planes and trains as everyone has suggested. Thank you again.

There seems to be some restaurants offering fixed menus. And I hate to
not use Dec 26 as a travel day (or the 25th) because things are more
generally closed those days. But December 25 is likely to be wholly
memorable if we stay in Florence.

I agree, stay and enjoy Florence on December 25th, especially in fine weather there are some parks across the river, walk up to Piazza Michalangelo & I don't recall the name but a church further up in those hills with fine views of Florence. And there's always church services! I dislike those Christmas & NYE set menus, tend to be pricey and too much food. Might sound weird, but we usually go to a pizza by the slice place on NYE, easy to find something open & no need to eat a large meal!

Thank you again. I’m sure we’ll be wide-eyed with wonder throughout the trip, especially during the slower opportunity on Christmas Day. Planning at first seems daunting, but ploughing through the first few iterations has created its own excitement. Happy travels!

Is this what you're thinking?
15 arr Milan
16 Milan
17 Milan to Madesimo, arrive hotel early afternoon
18 Madesimo
19 Madesimo
20 madesimo to venice, arrive hotel 2-3pm
21 Venice
22 Venice to Florence, arrive hotel early afternoon or later if you want.
23 Florence
24 Florence
25 Florence
26 Florence to Rome, arrive hotel early afternoon.
27 Pope

Yes, that’s the draft idea. We hope to have a day’s travel between each city, as Chris notes. We have not got much further, except to think about the Passo Tonale and its glacier for early snow. I know we’re not giving Milan, Venice, and Florence their due but it would be great to have another trip. Besides nailing down some of the cities, we still have the mechanics of the travel and the stays to do. For instance, the search for places in Venice, I’m thinking, should start around the train station since it could be that we arrive later in the day and I believe the city is very walkable, or is that part of town less likely to have accommodations? Alternatively, I’ve read in the forum that, upon arrival, getting on a vaporetto to the area one is staying is also a good idea. And I need to get schedules out to see how the timing of the different modes of transportation work. Still a lot of fun planning ahead!

Somewhere around day 8-10 should be a "chill out day" where you really don't have any plans during the day. Maybe something at night or a nice dinner but use this day to sleep in, vibe, relax, be a spectator, read, just chill.

I don't love the zip in/zip out Venice part. I just think you're burning a lot of time and hassle for relatively little sightseeing. You could borrow a day from Florence I guess, or Rome. I would probably borrow from Rome but I get the impression that's a big draw for you guys and the Christmas celebrations will be pretty cool I'm sure.

Thank you for your good suggestions. We’re revising things a bit: a day earlier into Milan, potentially creating another day in Venice, but as you noted Chris, Rome on a Sunday is one of the wish-fors. We tried flipping it over, but fear the crowds in the snow after Christmas. I see in some posts that smaller hotels are recommended. Do you have a suggested area in Rome for us walking-oriented tourists to stay, keeping in mind we are with a teenager and do not want to miss the major sights. We hope to go one day to a Pompeii and thinking another day to the Palace of Caserta, so how important is proximity to the train station?

I will not add to the previous comments, but address Pompeii and Caserta. Pompeii is a long, full day from Rome, and you need to consider winter with shorter daylight hours. If you really want to do both, I suggest planning two nights in Caserta. Take an early train out of Rome and visiting the palace in the afternoon. The next day take the train to Naples and change to the commuter train to Pompeii. Return from Pompeii and back to Caserta. Your other option might be to check out of Caserta and store luggage in Naples and return from Pompeii, retrieve luggage and return to Rome.

We spent four days in Caserta last spring which allowed us to visit the palace there, Pompeii and Hurculaneum. It all depends on your priorities and time. I also don’t know their closings or hours over the holidays.

Maybe some other experts will offer their advice. This is what we experienced.

Happy travels!