Italy in December starting in Milan

From Milan you could take a train to Florence, then take a train to Rome where you could fly out.

Pick up a guide book (see if your library has some) to narrow down what sites you want to see.

For accommodation reservations always book direct but use a third party (like booking.com) to search and read reviews.

Since your daughter (and her colleagues) will be doing on-the-ground research in their time off... enlist her to check a bunch of things out (while you are doing your guidebook research) ... and have her help you build the itinerary in early November. On the subject of flying in and flying out... Although you will just have your luggage for two weeks with you (carry-on only I hope), she will probably have quite a bit more from her sojourn. If she can ship it home from Milan freeing herself of carrying it, then flying into Milan and out of Rome sounds great. BUT, if she needs to haul her stuff home as "extra" baggage, you will both need to depart from Milan... In that case some of her baggage could travel as your checked luggage.

Where to start? Rick's guidebooks of course, and his many videos. Also check out Rudy Maxa and Samantha Brown. Make a list and then translate it to a calendar. Don't overdo it, there is way more in Italy than you can see.

Flying open jaw-into Milan, out of Rome- is always preferred
It saves time and money but do heed advice above about your daughter’s luggage

I wouldn’t expect either Florence or Rome to be “warm” in December
Not sure I’d want to be at Vatican on Christmas but YMMV!

Figure out how many nights you’ll have
Try to stick to 3-4 location changes and be in your departure city the night before your flight
If that has to be Milan then travel right away to your furthest destination and work your way back

Travel could all be done easily by train
With a good guide book and some research/ advice from this forum it should be easy enough to plan your own trip.

I use Booking.com and usually do book thru their site as I often get better discounts than with the hotel. It’s nice to have all your bookings in one place
I never book anything non refundable.
You can set your filters and really narrow down options.
Read the reviews closely for each property, only those who have actually stayed can leave reviews so you can trust they are accurate.

I feel for you! I travelled to Italy many times as a solo traveler for work. It was quite overwhelming at first. So I get it! You will have your daughter and her friends hopefully doing some planning ahead will be helpful. Reach out to her and see if she can come up with some kind of schedule once she has been living in Italy for awhile.The great thing is- you have taken the first step by reaching out to this travel forum of experienced, kind travellers that will give you lots of advice.
I agree with every single thing posted here! We have lived thru it and actually quite happy to help.. I know I spend quite a bit of free time on this forum and try to give some tips from my wheelhouse if they might be useful!
Next- if it were me….. just a couple of tips to reiterate what others have mentioned and some of my ideas.

First- get a map of Italy. I always start with a giant great thorough map. Rick Steves actually has a great one. Or just go online. This will give you an overview of where you may want to visit. And it will be invaluable as far as figuring out logistics.
Next- I agree with everyone on this one- Get some travel guidebooks on Italy. Figure out what may be interesting. Book some tix ahead.
- travel- the trains aren’t that hard to figure out. Read the forum and RS website for tips. Also. If you get into a train situation where you just aren’t sure. Just ask! Travellers are so helpful and kind. I don’t want you to get stuck anywhere, but in my experience- I owe my life to some that have helped me when I was lost. Just a BIG side note- be sure to PAY IT FORWARD. Us travellers research and plan and try to be professional in travelling. But those that help us when we are stuck deserve a standing ovation. Ok I’m getting a bit ahead of myself…
-Once you have done your bit of homeworK, and have some concrete ideas about what you and your daughter want to do… check back on the forum, you can get some great ideas about how to accomplish what you wish to do (skipping lines, great hotels etc)
If you are nervous about taking trains- look for tours leaving from Milan. There are lots of single day trips. Or hire a private driver. Much more expensive- I advise trains. But if it makes sense to you. May be easy way to travel. I love the trains in Italy. Cheap and easy. But you may need to do a bit of research ahead. Nothing difficult at all.

Next! Do your homework, book some things, keep in contact with your daughter about travel.
Last- I would always fly into Milan and out of Rome. Worth the extra bit to fly into one place and fly out of another if that’s your travel trajectory.
Best wishes! I hope you have a fabulous time! Sorry if this is so long, trying to make you feel
Comfortable about travelling on your own to Italy. Honestly, it’s a cinch if you do a bit of homework. I think you are going to have a great time. And the research and the planning on the internet! My goodness. So fun. As far as I’m concerned the planning is just as good as the travel.
I hope this helps….
Happy travels, Lisa

Milan 2 nights
Venice 4 nights
Florence 4 nights
Rome 4 nights.
Adjust one night up or down depending on your preferences/needs.
Fly out of Rome.
Transfers from place to place by high speed train (www.trenitalia.com or www.italotreno.it).

On both web-sites linked by Roberto, use a day of travel before December 11 to get an idea of schedules and prices.

The 2023 train schedules will be gradually uploaded in the weeks Leading to the December deadline.

I would use one of the 4 days in Florence to make a day trip, to Siena or maybe Lucca.

Wow! Thank you all for for your advice! I'm wondering what an average price for a hotel room is and have you noticed a spike this year due to the pandemic? Should all hotel rooms be booked in advance so we have a destination point in each city? I would love to hear about favorite places to stay, eat, visit, must sees that may not be widely known, small places that you discovered. I love train travel so looking forward to that! I need to put together a travel wardrobe for December weather too. I grew up in MN so understand cold weather clothing! Advice on clothing brands for women that travel well and are interchangeable for day-night. Should I bring boots or find a great pair there? I have the Away Bigger Carry-On suitcase that could be my only bag. Love the advice about having my daughter send most of her things home once she's done with her program. I have lot's of planning to do. Please keep the advice coming! Thank you!

As always, excellent advice from everyone. Regarding hotel research, you should also look at Rick Steves Italy travel guide. We were in Italy in May and June, in Milan, Rome, Pasteum, Florence and Venice. Our accommodations in Milan, Pasteum and Florence were in the Rick Steves book and we booked directly with the hotels (and agritourismo). We would stay at every place again! Our accommodations in Venice were via booking.com and again, we would stay there again and had no issues.
We were in europe for 3 weeks+, our daughter for 4 weeks, and we limited ourselves to one carry on per person and one backpack. While it is easier to pack lighter in the summer, I would pack light layers and stick with carry on luggage. We love the trains in Europe and its a lot easier to use them with a carry on.

You can use www.booking.com to check average hotel room prices in the cities you want to stay. There are prices for all budgets. At the end of June I stayed here in the Trastevere district in Rome. Great 3 star hotel. The price was about €150 per night, but the end of June is peak time and the same room would cost you less than half that in December, which is low season. Making reservations far in advance is not necessary, especially in low season. I booked the hotel above in Rome just a few days before going, and it was very high season. I would book only once you know your travel plans are set in stone, in December you can easily find hotels even on the same day. Venice is the only city where you should book a bit sooner than the others, but even there you will easily find vacancies in December.

Temperatures in Italy are never as low as in Minnesota. The northern cities (Venice and Milan) will be a bit colder than Rome, but even in Milan temperatures rarely go under 30F at night, even in December. During the day you should expect temperatures in the mid to high 40s or even low 50s. Rome would be a few degrees warmer than that.

If you plan to travel by train, pack light. You are the one who will need to haul the luggage aboard the train and place it on the overhead compartment. Having a huge suitcase is not ideal. If you can pack everything in a carry on size suitcase and in a small backpack that would be best.

To figure out appropriate clothing (and other stuff too) I use timeanddate.com to look at past weather conditions. I've linked to Rome for December 2021. You can look at any city for any month for the last ten years. Pay attention to the humidity as well as the temperatures. While 50 degrees may sound balmy, if it's really humid, it will feel a lot colder and it will stay with you longer because your clothes get a bit damp as well. For mostly outdoor days, thermal tops and bottoms are good. Most indoor places will be heated, so you'll want to wear layers for them. Churches are cold. With two weeks, you are likely to have at least a few sunny days when it's a joy to sit at an outdoor cafe with a cup of coffee or a glass of wine.

Yes, you should book all your hotels in advance. If you don't want to share a double bed (not queen- or king-size, which are rare), you'll need "twin" rooms, which are less common than double bed rooms. You'll be running into high season shortly after your trip starts. Also plan carefully for where to spend Christmas. Rome is usually very packed with tourists then. Many sights and restaurants are closed from early on the 24th and all of the 25th.

Does anyone have a hotel suggestion in the Brera area of Milan? Some place you love!
Also in Amalfi Coast for 4 night

Susan, your last posting ran up a red flag for me. You should check carefully as to whether the Amalfi Coast is a good destination in winter. I’m inclined to doubt it. At any rate 4 nights would be too much on such a short trip.
I recommend reserving a hotel, at least for Venice. On our first trip to Italy, (1984, pre-internet) we couldn’t find anything in our price range there. We settled for a hotel in Malcontenta, which was fine and just a 5 minute ferry ride away. Still, if you reserve only hotels with free cancellation, you have nothing to lose. I’d do it now. Btw, Venice was freezing, literally. It snowed while we were there, though nothing stuck to the ground.
Another issue to be careful about is holiday restaurant meals. As soon as you settle on an itinerary, it would be wise to secure dinner reservations for 12/24 and 12/25. 12/26 is also a holiday, so some places will be closed.

The best city in Italy is Florence by far! It also has many beautiful little towns and villages surrounding!

Congratulations on your first trip to Europe, you will love it! A lot of fantastic advice here, I especially liked Roberto's advice on how to structure your time.

I want to second the advice against the Amalfi Coast. The ferries will not be running and A LOT will be closed for the season. And there is not a lot to do inside. You could definitely have some dreary weather. That gorgeous, sunny, beachside visit will not be what you get in December. And it gets dark so early.

Also, about your question about boots, definitely get them at home and have them broken in, you will be doing a lot of walking. For our trip in May to Ireland, I loved having waterproof hiking shoes, I got Oboz because they were the lightest and most comfortable to me, I don't think you need the boots, though.

If being at the Vatican for Christmas is meaningful to you, then go for it! I would want to steer clear of it, it will be mobbed. I also second to get your reservations for hotels and restaurants immediately for Christmas, that is a very crowded time. I hope you find some fantastic cozy restaurants with a roaring fire! And some charming Christmas markets, maybe do a cooking class! Enjoy

Thanks Rosalyn for your suggestion. I'm wondering where a good place to be for the Christmas holiday would be. I decided not to go to Rome for Christmas. It's not important to us. So far I have only booked a flight into Milan 12/14 and out of Rome 12/28. My daughter suggested staying in the Brera area while in Milan until the 17th when she will be done with her program. Then we may take a trip to France because she loves it there, and then head south in Italy.
Or we will skip France and just explore Italy. She has mentioned that perhaps Venice will have a lot of rain and this isn't the time to visit there. And based on suggestions here we may just need to eliminate Amalfi Coast too.

I think since you have flights into Milan and out of Rome, you should limit your trip to Italy. I would not cut out Venice. It could rain at any of these locations and Venice has a lot to do inside. Get a vaparetto pass and when the sun breaks through, head out. Venice is so unique and breathtaking and it will be lit up so beautifully for Christmas.

Florence will also be lovely and day trips into Tuscany would really be great!

Since you are leaving from Rome on the 28th, you probably should be in Rome for Christmas. I wouldn't want to be trying to get into Rome for my flight with all of the holiday travelers, I would want to already be there. I think Rome would be beautiful and energetic! I just wouldn't stay near or eat near the Vatican. I would still want to visit it, maybe the 27th.

I would try to go for coffee, drinks or dinners sometimes in places with lit up pretty views on some of the less cooperative weather days. Relaxing and savoring everything would be the way to go.

We arrived in Rome the day you are leaving. You made a good choice! Rome was packed( with Italians) over New Years. It was difficult to cross through the famous piazzas due to crowds.

We are actually getting ready to head to Milan next week for a 2 week trip. Here's the itinerary we are planning on:

Flying into Milan and spending 3 nights there. We plan on doing a day trip to Lake Como. If you plan on seeing The Last Supper, be sure to buy tickets/make reservations in advance.

Taking the train down to Florence and spending 3 nights there. We may do a day trip to Pisa, but have left our itinerary pretty open, outside of a private cooking class that we've booked.

Renting a car in Florence, driving to Montepulciano and spending 3 nights there. If you are into wine and want to visit some of the wineries in the area, note that many of them require you make a reservation in advance - particularly in the off season.

Driving to Rome, dropping the rental car off and spending 4 nights there. If you want to visit the Colosseum and associated attractions, you will want to book that in advance as well.

We are flying home out of Rome.

I have used Rick's Italy book a lot to help map out the trip. All of the hotels we are staying are on his list of recommended hotels. I'll have his book with me and be using it the whole time we are there. We've been all over Europe many times and Rick has never led us astray!

What are some thoughts on this itinerary? Except that my daughter would love to fly to paris at some point! and not spend more than 2 days in Florence
Milan 3 nights: Fly in on 12/14, Lake Como day trip
Venice 3 nights
Florence 5 nights: day trips to Lucca and other areas. Spend Christmas eve here and leave for Rome on 25th. Or spend 3 nights in Florence and head to Naples for 2 nights and then to Rome.
Rome 3 nights and fly out on 12/28

Since you seem to be committed to Milan for 3 nights, definitely try a day trip somewhere, i.e., Lake Como, but remember it will be off-season. Wouldn't even attempt Amalfi. Personally, and know a lot will disagree here, 2 nights in Venice are plenty this time of year. We were there at Christmas a few years ago, and it was cold, damp, dreary weather with intermittent rain. Florence is a definite must. So much to do, and during the holidays you will most likely be able to find more restaurants and dining options for the holiday (but make those reservations!) (Was just there for 4th time the week before last.) We stayed this trip in a lovely 2 bedroom apartment overlooking San Lorenzo, one block from the Duomo, 5 minute's walk to train station, and there are tons of dining options available outside our door. Great day trip options from Florence. Siena, Pisa, Lucca, wine tours, Fiesole, and the central market is a lot of fun. If you don't plan on some day trips from Florence, 5 nights could be a lot. We were in Rome the week before last and it was an absolute madhouse. The crowds were overwhelming, and don't even get me started on the Vatican. Elbow to elbow, breathing everyone's air around you. Total craziness. Can't even imagine how it would be at Christmas.

A stop-over in Verona on your way to Venice might be nice. Quite a lovely town, and has the whole Romeo and Juliette thing going see (movie Letters to Juliette). Schtick but fun all the same. Another very lovely place from Florence on the way to Rome is Orvieto. IT has the most beautiful Duomo, underground tour, and the hill-top village itself is lovely. Easy train ride from Florence and easy to get to Rome from.

Milan 3 nights (since you are already committed to this
One night Verona
Two nights Venice
3 nights in Florence (you get your fashion, food, art, etc. here)
1-2 nights in Orvieto - or add a night to Florence
3 nights Rome (depending on stay in Orvieto)

You have so many possibilities

Edit to add: Roberto will always steer you in the right direction. His advice, even after multiple trips to Italy, has always paid off for us. He knows his stuff!

Best area to stay in Rome right after Christmas. Without a car so walking area. Hotel ideas?
Venice too! Thanks

Sounds like a great trip. Probably you have booked everything by now, but we stayed at a great little hotel in Rome right by the Pantheon called Albergo Santa Chiara. It was perfect and easy walking everywhere. We did a tour of the Colloseum that I highly recommend (through Walks of Italy). Also highly recommend booking a tour of the Vatican to help you cut through the crowds and navigate the vast galleries and space. Our kids were pretty young at the time so we did a private tour that was geared toward kids. It was $$ but that was one place I really wanted to see and I didn't want to have to chase my kids around while they disrupted a group. Have an amazing trip!