We have 4 nights to book and the weather looks rainy. Debating between staying all 4 nights in one city or splitting it between two. Unfortunately, the weather forecast looks rainy... where would you recommend?
On our potentials list so far:
Cortona
Florence
Siena
Lucca
We've already done a lot of Hilltop towns.
Also, WHAT do you recommend doing when it's rainy? (Any specific tours, classes, museums, etc??) Thanks in advance!
Cortina’s a hilltop town, so that might make it less appealing from the start. There’s a city down below, where the two train stations are located, but we spent all our time up in the walled old town. Other than the MAEC museum, our B&B, the slow line at the post office, and restaurants, all the rest of our time was spent outside, exploring the streets, lanes, and the piazza.
Lucca - wonderful for exploring as well, but that’s mostly outside, including walking and biking on the pathway atop the town walls. Churches and shops, and a museum that we didn’t see, but not a lot of shelter when it’s pouring rain for 4 days.
Siena - up on a hill, a magnificent church inside (and also see up high, if you do the tour), plus the town hall & museum, so that’s better than Cortona or Lucca in your situation, but …
Florence - lots of fairly close-together museums and churches to duck into and out of the rain. Some require pre-booking admission, depending on time of year, but there are so many that you’ll easily fill 4 days with fantastic art and history. There are also some taxis, which could save walking in the rain.
By the way, Bologna is known for its porticoes, covered sidewalks, but they’re not waterproof by any means. We walked one day to the MAMbo modern art museum, and it was pouring rain, some of which blew sideways into the portico. They get slippery when wet. Also, if there’s an intersection and you have to cross a street or alley to get to the next portico, that street or alley crossing isn’t covered, so you’re temporarily getting rained on any time you’re not under the portico roof (and sometimes even when you’re under the roof).
At least you’re not going to be way south, in Lecce. It’s a fabulous town, and we enjoyed our time there last fall (and going back again this fall), but it has no rainwater management system. It rained a lot, and there are no drains in the gutters, so the streets become rivers with splashing cars, and rain gutters on buildings just drain onto the sidewalks, which become canals.
If not Florence and it's many museums, Bologna may give you the most options, so maybe add time to your stay there. We were there in March 2025. The day we planned to explore Bologna, mostly outside walking, it was rainy so instead we took the train to Modena, went to the Ferarri Museum, then over to the market for lunch and walking around. We did walk outside for 10-15 minutes between the museum and market and back to the train station, but we were fine with rain coats.
If you really want to splurge you could look into the Italian Days food factory tour, it's a full day but very interesting and delicious, includes breakfast and a marvelous multicourse lunch. You get picked up in Bologna and everything else is indoors.
For a stretch of rain? Florence. There are a ton of 'indoor' things to see there (museums and churches); enough to easily fill 4 days. Yes, some of them do require advance reservations. But a question? Are you in Italy NOW? Forecasts aren't usually all that accurate for more than a handful of days out.
Editing to add: Cyn brought up a really good point about dealing with rain, especially in the old cities. All of those cobbles and pavers and stone steps can be deadly slippery when wet so be careful wherever you end up!
I see from a previous post that you are interested in architecture? There's a ton of that to admire in Florence too. Do be aware that if you're in Italy NOW and planning to book for a stay in the very near future that the city is going to be very, very busy.
Been to all these places and love them all. Don't need 4 nights in Cortona.
I would go with Florence if the weather is rainy. There are some great museums there.
Lucca would be good for a couple of days, but mostly out side.
Siena has a lot to see, it would be my second choice.
Thank you for all of the ideas. Ferrari museum and food factory tour could be good indoor activities. Yes, it has been very busy with the holidays!
