Best of Italy in 17 Days - September or October?

I would chose Sept. 15 - Oct. 15. In autumn there is an increased chance of rainy periods lasting 3-4 days, but there's no predicting exactly when. Any hot or cold spells then will not be extreme and should be short-lived. September and October are the peak months of cruise ship traffic, but c'est la vie.

I would pick a tour start date between Sept 8-18.

I did this tour Sept 30-Oct 16 2022. It was not too cold in the Dolomites, in fact I think I was in short sleeves the day we hiked up in the Alpe di Siusi (jaw dropping!). It WAS too hot for me at the end of the trip in Rome. That Fall was, I think, warmer than "normal" (what is that any more??) and was in the 80's in the city. I don't tolerate heat very well and I'm also pretty cold tolerant. We did have quite a bit of rain but it did not really impact touring for me. Be sure to have a waterproof rain jacket with a hood. No need for rain pants or waterproof shoes in my experience (not like the Scottish Isles!).

https://community.ricksteves.com/travel-forum/trip-reports/best-of-italy-sept-30-october-16-2022

In years past I've been in Italy the 1st week of Sept (Venice, Florence, Rome and CT) and it was hot. I've been later the same time frame in Late Sept/early Oct but was not as far south as Rome so it was not quite as toasty. We ended in Milan in mid-October and hit rain.

I think your choice depends on how well you tolerate heat. I don't think October is too late for any of the tourist areas although I'd probably want to make sure the Dolomites were 1st - 2nd week of October.

BTW, in your planning, I'd suggest a couple of nights in Milan before the trip and I'd also recommend an extra night in Varenna. You are really only there for 1 full day and there is more to do around there than that. I'd also suggest a night or 2 at least in Rome at the end. I only stayed 1 extra night so I had an extra full day in which I did the Domus Aurea (Nero's Golden Palace) and the Borghese Gallery but I'd been to Rome a couple of times before.

This trip is an excellent sampler!

Thanks for the information. It is useful and much appreciated.

I've been in Italy multiple times during this time period. It's great that the tour goes southbound (for optimum temperatures). The earlier in September, the more crowds, in my experience. I'd go beginning the last week in September if possible, for those 2 reasons. Have fun1

Joan and Pam had similar experiences as we did…and I’d also recommend late Sept. into October for timing. We took the My Way tour last fall, September 26-October 8, then added on some extra days at the end in Rome and Orvieto. It was warm enough to swim in the sea at the Cinque Terre, and I was uncomfortably hot in Rome on Oct. 8-10. However, these dates seemed to be the sweet spot for travel for us, starting north and moving south…and a few days after we got home, there were torrential rains in Italy, flooding the streets in the CT and Rome. Then the temps dropped. We had no rain at all on our trip.

There were a lot more people than we expected in the CT and Rome, and it seems there’s no “shoulder season” in Italy any more in terms of crowds. Taking a sunset cruise in the CT helped a lot…that was a gorgeous experience and a relief from the masses of people on land. https://rosadeiventiboattours.com/en/

Also, choosing to end our busy time in Italy by staying in lovely quiet Orvieto was a highlight for us. An easy one hour train ride from Rome. It was beautiful, and easy to take the train to the airport area when ready to head home. We stayed at the Hotel Tiber in Fiumicino for our last night, saw the sun set over the sea while savoring our last gelato, and shuttled to the airport the last morning. It worked well for us.

Enjoy!

The later, the better. We had a great three week trip this past October through the first week of November using the Rick Steves guidebook suggestions, doing a Milan roundtrip loop. Although the mountains may be cooler, I don't imagine they would be "cold." It was nice to avoid the crowds in many of the stops. We even had some rain in the Cinque Terre and hiked safely, where it was allowed, anyway. Enjoy!

Do not go in September or the first week of October. There will still be summer crowds and summer heat/ Mid-October is my suggestion