Pre-book hotels in December- January travel

Hi Andrew and welcome to the forums!
First things first, more information would be helpful:
What exact date would you be departing California?
What exact date would you be departing Milan?
Were you planing on going immediately to Naples upon arrival in Rome?
Have you done the homework on driving in Italy?

I'm seeing some red flags in your plan but don't want to make any assumptions. Biggest issues are a potentially jet-lagged drive to Naples in the dark (most folks here wouldn't drive in Naples in daylight!), renting a car on Christmas Day, the actual count of nights, not days, you have on the ground in Italy, and trying to manage 6 destinations in that amount of time. Those 6 are:
Naples
Positano (day trip)
Rome
Florence
Venice
Milan: you'd need to be in Milan the night before your flight.

2 nights anywhere only gives you 1 full sightseeing day.

That's a very, very rushed itinerary, and I'd personally nix Naples and Positano right off the bat as it's not a great time of year for the coast. What more can you tell us about this trip?

To add: I don't know what your sightseeing plans are but you'd be working around New Year's Eve and New Year's Day. Expect practically all attractions to be closed on Jan 1. I won't swear to it - other posters here will hopefully confirm - but I'm betting you need advance reservations for dinner on New Year's Eve, and possibly New Year's Day as well. Same issue on Christmas Day.

You seem to be assuming that it is a quiet time of year, but it isn't. It is very common in the UK and Europe for companies to shut down the week between Christmas and New Year vs the US only giving Christmas eve, day and NY day. This means lots of people traveling, especially in the warmer southern European countries. I suggest you look at your dates in booking.com to get an idea of how many accommodations are sold out and what the prices might be. I am currently booking for a trip to Barcelona mid January and the apartment hotel I booked is 90-180E per night mid January, but I noticed it is 500E per night Dec 27-Jan 1 with only one apartment remaining.
Edit: The 500E is even higher than they are quoting for April which is a busy month in Barcelona, so suggests to me premium price nights.

hey hey andrew
totally agree with what kathy and syd have mentioned. my own opinion is the risks are high getting room/rooms during that week. don’t know your budget in euros. so many travel during holidays and booked months & months ago, families spending time together with many places closed. you may be biting off more than you can chew.
6 very busy crowded cities in 11 days, unless it’s 9 with first and last day are travel days, check-in is 3-4pm check-out 10-11am.
learn traffic/road signs and what they mean, do’s & dont’s, parking available or “down the road & how far”,
do you have an IDP for each driver? check AAA.com
I would omit naples and positano this trip. spending too much time looking out window of cars, trains/buses.
too many travelers try to see too much in short amount of time. your wants are from southern to northern italy. I would think it over again, what is most important to see, okay to miss
it’s your holiday and your decision
aloha

Thank you all. I have 11 full days, arriving in Rome 12/25 and depart Milan on 11/6. My 2 teenagers are not keen on visit too many museums and like a faster pace, thus my initial take of Naples and Positanos. That said, I will take the advice and skip Naples and Positanos. So that leaves 4 destinations, Rome, Florence, Venice and Milan.
The tour books generally cover summer travels so planning a winter holiday is a bit challenging in knowing what’s open or close. What would you recommend an itinerary now, factoring possible closures:
Rome-4, Florence-3, Venice-2, Milan-1

arriving in Rome 12/25 and depart Milan on 11/6.

Either your dates are wrong or your count is wrong. I count 12 NIGHTS in Italy

Rome 4
Florence 4
Venice 3
Milan 1

Puts you in Florence over New Year's

Again- counting your trip in NIGHTS gives a clearer picture.
And no way would I travel at that time of year without confirmed reservations everywhere. You'll most likely need 2 hotel rooms for your party of 4. Not many hotels offer rooms with beds for 4.

...arriving in Rome 12/25 and depart Milan on 11/6.

Yep, I'm counting 12 nights, 1 partial day (arrival in Rome) and 11 full days. The order is fine but how many nights to stay each place depends on your sightseeing interests. Florence is great. I loved Florence but I'm an art, architecture and history geek, and Florence is a museum-heavy city so it worked for me. Your family? You probably want to look at taking some day trips, just not on January 1. The historic center of Florence is reasonably compact; you can pretty much walk everywhere. For day trips, you could rent a car for a day - DO read up on the ins and outs of driving in Italy, especially ZTL areas - or choose destinations easily reached by train or bus. Look at Lucca, Siena, Pisa, etc.

Italian trains are pretty great too. :O)

Rome is gifted with ruins, catacombs and more glorious churches you can shake a stick at. It also has terrific smaller art museum (Galleria Borghese) that we enjoyed much more than the Vatican's museums 'cause they have such good crowd control. We found Rome to be entirely walkable as well.

Venice? It has been a long while since my last visit to be seen on foot, or take a vaporetto to one or more of its islands.

But what are your teens interested in? What have they said they'd like to see?

Same as the others above, I'll strongly recommend reserving your accommodations ASAP. The holiday season is not a 'low season' quiet time; the Italian Christmas season doesn't really end until after the Feast of the Epiphany on January 6, which is also a public holiday. Hotels that can accommodate 4 to a room aren't plentiful either but look for those which advertise "family rooms" such as this one in Rome:

https://www.hotelpresident.com/en/home-page.aspx

Some may only accommodate 3 people, and you want to check locations carefully as a listing can be for, say, Rome, but be far outside of the city center. Depending on the age of your teens, they may be considered adults, as they would be if booking the hotel I linked above. That could affect availability. Whatever the case, you do NOT want to be running around with your luggage trying to find a place to stay.

Great advices. Is there anything to do at all in Florence on New Year’s Day?

We continue to travel without advance reservations but we have done it for 50+ years. In the past we always used the TI, generally in the train station, when we first arrive in the city. You learn to be flexible. We now depend mostly on the hotel and hoteltonight apps and book one to two days in advance. It works for us and we have not slept in the train station, yet --- but, I suppose, there is always the next trip. We are comfortable doing it but many like to reserve everything down to the last hour. At that time of year you might be more comfortable booking in advance.

It's tougher to find space for four people (and massively tougher if you want them all to be in the same room) than two, just as it's harder to find a hotel with a room available for 4 or 5 nights than just a night or two.

Any city with a large historic district will provide many hours of pleasant wandering as you gawk at the interesting, different-from-home architecture, but not everyone is as interested in doing that as I am, and of course it's not necessarily all that pleasant if you're unlucky with the weather. Rome has the iconic Colosseum and Forum which can be seen to at least some degree from outside.

Italy has uncountable lovely churches, and they are often open when other points of interest are closed. However, except for the famous ones mentioned in guidebooks, it's not always easy to find information online about when they will be open.

Places you'll need to reserve in advance if you want to go inside them:

Rome:
- Vatican Museums (possibly already too late for dates in late December). They will be an overcrowded zoo and require a major time commitment. Your time might be better spent elsewhere. Just walking around Rome, stopping for gelato and pizza, is a fabulous experience.
- Colosseum (probably too late for online tickets for dates in late December, but you can line up at one of the ticket offices)
- Borghese Gallery (probably too late, but this is an art museum)
- San Clemente (buy ticket online before going to the church; one day ahead might be OK)
- Domus Aurea (you might get lucky with a late-December entry, but I'm not sure)

Florence (I think--haven't been there recently):
- Uffizi
- Academia
But those are both art museums that might not interest your family

Venice:
- San Marco (probably too late for online tickets, but the long line moves pretty fast)
- Doge's Palace (probably; I skipped it)

Milan:
- The Last Supper (very, very difficult ticket)
- Duomo roof climb (probably need to prebook, and it might already be too late)

Thank you all for your insights. I too have travel much and prefer only one or 2 days pre-booking. But it’s mostly travel with 2 people and never over the holiday break. Anyway, I will firm up my plan and start booking everything.
Thank you again for generously sharing your thoughts. Your advices are invaluable.