Recommendations with an artist in mind

Jen - Base yourself in Milan Italy. You will have options to visit many places from there. You can visit Lake Como and the various lake town villages on the lake. From Milan, you can visit Bergamo, Lugano Italy, and Bellinzona Switzerland. Furthermore, you can day trip to Lake Garda, Lake Maggiore & the Borromean Islands, and Verona from Milan. All these places are accessible through public transportation.

One more thing, there is a charming wine region just an hour from Milan. There are shuttle buses from Milan that takes you to the main town of the region, Iseo. If you want to do some wine tasting then head there for half of a day or a day.

https://www.cntraveler.com/story/a-guide-to-franciacorta-italys-most-chill-wine-region

https://www.italymagazine.com/featured-story/gem-lombardy-travel-guide-lake-iseo

https://www.travelandleisure.com/trip-ideas/nature-travel/lake-iseo-italy

Another thought: Base yourself in the beautiful medieval city of Perugia in Umbria. From there, you can day trip easily by train to Arezzo, Todi, Spello, Spoleto, and even Assisi.

I liked Padua. It has a nice historic center and quite a lot of worthwhile sights (pre-book Scrovegni Chapel) and it's convenient for day-tripping to Vicenza, Verona, Ferrara and--if you're heading to off-the-beaten path spots and don't mind being there during day-tripping hours--Venice. I'm sure there are other interesting destinations I haven't been to, especially northeast of Padua.

Bologna, a city with a massive historic district, is also an excellent base for a wide variety of day-trips. Even Ravenna is within reach

If you mean you're looking for a single place from which you could day-trip to both Venice and northern Umbria, I don't know that there's a good solution.

Before making a final decision, check the rail travel times to places you'd want to go on trenitalia.com. Also note that round-trip fares to destinations requiring use of the fast Freccia trains can be very costly if the tickets are not bought early.

"Before making a final decision, check the rail travel times to places you'd want to go on trenitalia.com."

And don't just check how long it will take - check when the trains actually run. From Bologna, I found that to make day trips work well, I had to get up and on a train earlier than I would have liked, to avoid arriving too close to the lunchtime shutdown that would crimp my sightseeing on a day trip.

I agree that Padova and Bologna make good bases.

Too true, Harold. I'm famous for arriving at my day-trip destinations after the local tourist office has closed for the mid-day-break, leaving me with no convenient source for a paper map of the town. (I've been known to go into a hotel, place a one-euro coin on the counter and beg for a map.)

Hi Jen,

will you be painting on your day trips? Somebody mentioned Bologna and it is a good suggestion - though Florence would also work. I have a passion for painting medieval buildings, so Tuscany is a big pull, but the train network is mainly focussed on the Florence Rome axis and across to Pisa - the whole area around Siena is quite slow to visit - though they do have good buses.

From Bologna you could go down into Florence/Tuscany - across to Ravenna - up to Milan and Verona etc (see the Castelvecchio museum in Verona if you go) and even over to Genoa - which is fantastic, and Turin. Good luck!

Milan is not my favorite city. You omitted the month, which is important for volume of tourists. If you can manage it, I suggest Venice - long advance reservation and money required. There are a lot of nearby places to visit without a car. You need to research organized bus tours that might? be more available in high or shoulder season. Years ago we found some like that, in Florence. Don’t overlook Palladio’s buildings that are open to the public, or the Villa in Stra.

Perhaps Vincenza or Padua is a second choice, but you’ll regret not being in Venice!

Edit: You didn’t say if you are painting or looking at art.