Florence for 9 days in January 2025

You have many opportunities for day trips, even in the depths of January. Just dress for the weather. Cinque Terre would be a big no. Definitely not in winter. Pisa is more than just the tower. The Field of Miracles also contains a lovely Baptistry and church. You could combine it with Lucca in one day. Siena is also a nice day trip. Take the bus rather than the train. Venice is a little over 2 hours away by train. Technically possible as a day trip but exponentially better if you spend a night or 2 there.

We spent a couple of nights in Orvieto (2 older teens) in march and they loved it (and so did i)....you would see more if you spent a night, but I think it could be done in a day from florence via train...it would just be a very long day. food was great and they have their own local wine. There are like 9 (?) attractions covered by the orvieto card and we hit them all but you could prioritize.

we also did two nights in venice. they also loved, but I'm sure we didn't do it justice, saw only highlights ( st marks, doge's palace and views).

or, what about a day trip to Lucca? That was on my list but we didn't get there.

IMHO the most spec tacular day trip from Florence is Siena -- about an hour and 15 minutes away by bus. The Cathedral is jaw dropping and climbing the Torre Mangia is life altering.
https://janettravels.wordpress.com/2011/09/18/climbing-the-torre-mangia-at-67/

Lucca is also quite interesting.

We loved staying in Santo Spirito! It’s such a great neighborhood and you’ll really love just wandering around. The Basilica right there in the piazza is really beautiful so make a little time for that!

I also highly recommend the Palazzo Vecchio Secret Passages Tour. It’s really fascinating and was a highlight of our stay. There’s a tower you can climb there, and my teen son also loved climbing the Bell Tower.

We did go to Cinque Terre and it’s a little hard to say what January would be like but the views would be breathtaking in any season! We visited the Leaning Tower briefly on our way back.

A 22-year-old male will like Pompeii and the big sites in Rome like the coliseum rather than museums. He should also enjoy the tunnels in Orvieto. Unless your son is really into art, I would just spend the las two nights in Florence. I took 3 kids to Italy for their 21's birthdays. The girls liked the art, the boy could care less about that. All of the kids liked Rome, jazz bars in Rome, Sorrento, Pompeii, Orvieto and Assisi. J

There are lots of good day trips from Florence. Siena and San Gimignano by bus (not on the same day!), Lucca by train as well as Pisa. Remember that you will have fewer daylight hours. I'm told there is more to see in Pisa than just the cathedral campus (all I visited), and more to the campus than just the tower, which you can climb. The church is worth seeing and the baptistry is beautiful. I spent several days in Bologna and enjoyed it. The university's medieval sections are well worth seeing. Don't plan too many day trips, Florence is THE mecca for Renaissance art, sculpture and architecture. My favorites are the Bargello museum , the Baptistry and the Opera del Duomo Museum. The Medici Chapels are lavish.

You say that your son and yourself are interested in opera? I suggest that you check out the Opera at St Mark’s English church in the Oltrarno neighborhood of Florence. I am not a major fan of opera, but have attended two performances in the past and really enjoyed both. The price is very reasonable, and all proceeds to charity. The performers are all Italian opera professionals. Even those in our party who thought that they disliked opera thought it was wonderful. Highly recommend this experience!

Thank you so much to all for your wonderful suggestions and for bringing light to some misconceptions (such as Pisa) - we will have overall 8 days if Florence so plenty of time to travel in its vicinity - we looked up Sienna and your other suggestions and we put them on our 'to-see' list.

Thank you again to all - you rcomments are so appreciated!

If the weather is good during your stay - sunny (and it can often be in Liguria, that's why a lot of people from Milan spend the winter in places like Lerici just down the coast from Cinque Terre), January is one of the few times of the year when there are fewer crowds. This was our day trip there in January - you will be surprised at how many people are on the train, but not many on the trails:
https://slowtravelitalyspain.blogspot.com/2020/02/la-spezia-in-january-manarola-to.html

We both enjoy museums, gallerias, opera, theater, ballet, classical
music.

If you and your son both enjoy museums, you'll be spoiled for choice in Florence! Yes, many of them are art-focused but in the cradle city of the Italian Renaissance, there's good reason for that. I'm just guessing you know that already, it's a reason you're choosing to hang your hats there for over a week, and your young opera fan will be fine with that? Give a shout you want some suggestions.

And don't forget the churches! The best of them can be considered museums in-and-of themselves. :O)

Restaurants: a couple of recent threads with suggestions for those:
https://community.ricksteves.com/travel-forum/italy/which-florence-restaurant-would-you-choose
https://community.ricksteves.com/travel-forum/italy/florence-lunch-or-dinner-suggestions