I brought a sketchbook on my first trip to Italy.
My partner and I took advantage of a sale on Icelandair for $400ish from the East coast of the US to Rome and spent ten days in Italy (8 nights in Rome, 2 in Florence) this month. It was my first trip to Italy and really my first trip to mainland Europe and I brought a sketchbook and watercolors.
There are pros and cons to going in January, but overall the crowds were much smaller than anticipated which was lovely. We still had gelato every day and ate outside more often than not (I am grateful for long underwear and outdoor heaters.)
Each painting is labeled. It turns out the cute alley in #5, Via dei Leutari, was the site of some serious intrigue and murder in the 1500s. I'm sure there are similar stories for any little street in Rome.
The way ancient ruins are interspersed in a modern city with Baroque fountains and renaissance buildings is very cool). And one of my favorite things is all the ways Italians eat (and drink) artichokes (last picture.)