Italy in January

We lived there (Roma) for several years and found winter trips a delight in that we could visit museums in Firenze without worrying about crowds. We still reserved entry to the Accademia and Uffizi, but otherwise wandered in and out of many museums and churches without pause. Hotel rates are lower too! Take a look at Hotel Pendini in Firenze for a very nice stay at an off season price.

Roma is great, too, in January and has many options regardless of the weather. Too much to do, actually!

Siena is, IMO, miserable in the rain. I would stay in Firenze and Roma. Day trip to Siena from Firenze and to Orvieto from Roma. If you get a spell of great weather and wish to roam farther afield, Castel Gandolfo makes a nice outing as does Tivoli for the Villa d’Ests.

Thank you Laurel.

Oh yes, oh yes. As Laurel and I have recounted to each other, winter is the time to get the essence of the Italian cities. I hate lines, queues, anything that makes me wait. In high season, from that standpoint Rome & Florence would be unbearable. We've been twice in February & March, and--especially on weekdays--we basically have the place to ourselves, with the only caveat being Florence on the weekends--pretty busy even in winter. In Rome, we bought a weekly bus/Metro pass and traversed from one end of the other, and everywhere in between. Going the wrong way on the Metro? Who cares? Let's see where this takes us.

Couple things, however. Siena and Orvieto may be a bit quiet during those times, where 3-4 days might be a little much. As Laurel said, though, in Florence or Rome you absolutely will not run out of things to do, and you'll be highly efficient as well, the key being that it will allow you time to sit back on a nice winter day--if it's 55-60 degrees you will be able to sit outside--and savor just being there.

However, it being January, weather could turn on you at times. Not really a problem, because to me the lack of crowds offsets that every time. But dress in layers--to peel off when the sun comes out--and have a small retractable umbrella with you. What worked for me was one of those lightweight down jackets that folds up into its own pocket, to the size of a softball. Came in handy more than once. Stocking cap & gloves too, for morning walks along the Arno or Tiber.

You'll love it--enjoy your planning!

Thank you both so much for this advice. I have started looking at the day trips and tours from Florence and Rome on a site called Viator. Any other sites you could recommend? Pick up and drop offs to our hotel without having to worry about driving or taxis to do these tours right now seems the smartest thing to do. I have been finding some amazing deals on Air Bnb's and I love the idea of staying put in one place and split the trip between Florence and Rome. I am not one for crowds and either are my daughters, so travelling at this time of the year is going to be perfect for us

We want to do a day of wine tours and tastings from Florence so if you have any companies to suggest that would be awesome. Is it worth heading out to the wineries that time of the year?

Viator is a consolidator. Tell us which places you want guided tours for and we can recommend places to direct book.

Check out Tours by Roberto for a day in Chianti. He is delightful!

I did check out Tours by Roberto and there are no dates available for Jan 2020 yet, or he may not do them that time of the year. As far as tours go we would like to do the winery and tasting and lunch tour from Florence and one from Rome because I want to see Orvieto.
Other than that we are good with hoping on the train to go to Pisa or other places unless we can find a good price for some day trips to the coast from Florence