If you had 28 days in Italy, which time period would you choose ?

I'd prefer as early in October as possible. The days will be longer, the temperatures more mild, the weather...better? Better odds of good weather perhaps.

Mid-October should be well past the main tourist season, but I wouldn't expect Florence or anywhere else to be empty. Cheaper a month later? Perhaps, but by how much? Hotels cheaper off season is about it. Not sure it would matter much. I'd still go earlier rather than later.

The later in the year, the less crowded and (somewhat) less expensive your trip will be. Also, the later you go, the shorter the days, and some sites may have shorter hours. Some places may be closed until the next spring. The landscape in the country or large parks will be barer. Rain will be more frequent.

I would rather spend slightly more and go earlier in the fall (Oct/Nov). The worst of the summer crowds will be gone, but the weather will still be pleasant. Personally, I'd rather travel in early spring, but that's just me.

Every time I search for airfares they are always the cheapest mid November to mid December compared to mid October and most other times besides after the 2nd week of January.

You are accustom to cold weather just like I am living in Chicago so that will not be an issue in Italy where it is just chilly by comparison in winter especially when the sun goes down which by the way is early.

The South will be a different temperature from the North. So I wouldn't hesitate to go with December in the South. It might be nice to see some Christmas preparations, too. October straddling November could be great, too. You have a lot of time, so you won't feel pressured if you have a couple of rainy days. Weather has been strange these past years, however, so I would google "months most likely to have rain and floods in Italy."

As for Hotel Prices, I have found that Sunday through Thursday is when you find Hotel prices are lower - and sometimes the weekends show expensive prices. I am forced to spend max dollars in flights and hotels when I attend my special conference in Heidelberg during the last two weeks in July - yes, ugggh. Doesn't matter when I plan that - it's just maxxed out.

None of your time periods will assure you temperatures at or above 10C in Milan. Milan's average low temperature in October is 9C, so I'd expect some days colder than that. Its average high is 17.8C. In November the average high temperature is only slightly above your minimum, at 10.7C and the average low is 3.7C.

Florence's average low temperature in October is barely higher than Milan's (10.1C), but it does warm up more in the daytime, to 20.9C for an average high. The averages in November are 5.1C and 14.7C.

Rome and Naples are a good bit warmer.

The shorter days and less daylight would be a problem for me. Milan is especially grim, with only an average of 66 total hours of sunshine for the entire month of November.

The above statistics are from the weather summary charts on each city's Wikipedia page.

Mid oct o nov, realize u may have some rain during that timeperiod.
Take waterproof attire.

Although our 'sweet spot' time to travel to Italy has been late February/early March, we did do a mid-to-late October trip to Sicily, Rome & Florence. Personally, it was more crowded than I would have liked, and that was 8 years ago, with increased travel to Italy from the US since then because of the dollar & Euro creeping closer to par compared to 2010, when it was 1.43:1.00.

Even though it would be cool to see some Christmas decorations--that's on my bucket list, Xmas in Italy--I'd take the entire month of November, and frankly I'd have Florence as my northernmost (and starting) spot. A month really gives you a blank canvas to paint. 5-7 days in Florence/Tuscany & its environs, with day trips, then maybe a couple days in Orvieto, then Rome for 7 days, a hike over to the Bari, Lecce, Polignano a Mare area in 'the heel of the boot' in Puglia for a few days, then back to finish up in Salerno, Sorrento & Naples. Be advised that most of the Amalfi Coast will be shutting down for the winter, but Sorrento is still open and the whole peninsula is drop-dead gorgeous any time of year and is worth a trip.

So...fly into Florence, out of Naples. Yeah, you'll get some inclement weather, but mostly 40's-60's (Fahrenheit).

Enjoy your planning!

For what you want to do (towns and villages), even November is too late.
As early as you can go in October the better the chance for less inclement weather, although end of October and early November is generally wet.

Florence and Rome are never empty of tourists; and with the December holiday season and school vacations, they may even have a bit of an upsurge. With 28 days, you have ample time; but I wouldn’t spend much, if any of it, in Milan.
We have been in Italy twice during December. Both times we had pretty good weather, except for a freakishly cold spell in Venice. Actual snow, which, however, didn’t stick. Nothing to daunt a Canadian.

Sicily is pretty wonderful during the Advent season. Church decorations are amazing. I think the same would be true of Naples.
You can go to sites like booking.com and skyscanner.com to compare prices for different dates. No matter which you choose, Italy is wonderful.

By mid-October you would already miss the crowds of more popular months but would have longer hours of daylight and likely better weather than your other 2 options so would be an easy choice for me.
Florence, Rome, Venice will have crowds all 12 months of the year so for me the difference in a few less people around in end of Nov. but worse weather and shorter days would not be worth the trade off.

It should be low period in terms of pricing so expect all 3 options will be similar, last option at the very end could approach close to Christmas Holiday upcharges on things like the flight home.

We went mid-December, leaving a week before Christmas.

I was concerned about the weather. We ended up having nice weather with daytime temps between 10 and 15c. We did have a little frost one morning, but it warmed up. We only had one day with a little drizzle. The other days ranged from mostly cloudy to brilliant sun.

I'm not sure when low season starts, but we definitely had low season rates. We were also the only guests at our agriturismo and were pampered by the staff. We stayed at the winery Castillo di Verrazzano and the owner and wine makers were testing the new vintage at lunch the day we did a food and wine pairing. The owner invited us to join in and we had a great afternoon sipping great wine and making new friends.

The Christmas decorations were up everywhere and very pretty. There were also numerous Christmas fairs.

To be honest, if I were doing towns and villages and not worried about swimming, I would do mid-September to mid-October.

Anyway, of your choices, I would pick the earliest one for the best hope of more decent weather.

We had a lot of heavy rain in southern Italy in October.

I'm looking forward to when we can start going in mid-October. Mild weather, smaller crowds and airfares (at least from Seattle) are about half the usual cost. ($500-$600 USD versus $1100-$1200 USD).

Here's a chart of numbers of tourists to Italy by month. I find this kind of thing fascinating:
https://www.statista.com/statistics/654523/number-of-monthly-arrivals-short-stay-accommodation-in-italy/

Michael--

I am blocked from seeing the graph by the Statista site wanting me to pay $49/mo--uh, no--but I can assume what the data shows.

I would have been interested, however, to see how tourist visits in the 'shoulder' months--March/April and October/November specifically--have increased and also whether that increase makes high season visit totals decrease. My guess is that it would not, that travel to Italy is up across the board.

Huge key to traveling offseason is how to plan for inclement weather, not only from the clothing standpoint, but also logistically. You want to base more in the cities where more is going on. When there aren't tourists, it's just natural that tourist-based businesses and attractions will close down. The Amalfi Coast in January and February is damn near deserted. That being said, done right it's a wonderful time to visit there.

And of course there's simply getting your mind around the cold, wind & rain factor that can crop up at any time. For us in Sorrento in early March, in 3 days of driving rain, we convinced ourselves it was still better than being home, and took the train to Naples to see the Archeological Museum.

The more people who choose iffy weather/fewer crowds/shorter days over better weather/worse crowds/longer days, the better it is for me-me-me. Go for it!

Thank you all so much. Sorry it took me a few days to get back on here to thank you. I was laid up in hospital. Thankfully I don’t have a trip this fall.....LOL

Looks like mid October to mid November wins. We own a summer business so until we retire that is out of the possibility. Can’t in January to April cause that is our reservation season. Stuck with fall travel. We did the UK last fall during the same period and only had 2 bad days for weather really in 35 days there. So I’m sure it will all work out.

When I saw the title of your post I was going to respond "The Renaissance." Then I read the post.

I think you've made a good choice. Enjoy your trip, and best wishes on your recovery from whatever had you waylaid!

When I saw the title of your post I was going to respond "The Renaissance." Then I read the post.

Just need to know where Sherman and Mr Peabody left the 'Way back machine'

We are on Lago Maggiore (northern Italy) and October weather has been perfect. But not light until about 8am and dark by 7. Leaves are just starting to change and fall.

Renaissance might be interesting, but the lack of cleanliness of people and the environment in general kind of is an off putting thing most people don't think about. Also, I would have to learn Italian or Latin to be able to communicate. Probably need to find a few Florin as well, doubt the modern Euro would work and no ATMs on the corner. Might take me a while to get ready for that trip. :-)

Actually, I enjoy mid September to mid October in Italy any year. The summer heat is mostly gone, but the winter cold has not reached most of Italy by then. Children are back in school. Most tourists are done for the year. Makes for shorter lines at major attractions (although there always seem to be lines now) and somewhat lower prices.