There used to be a time that October in Italy was the start of the slow season, when prices dropped as the bulk of the tourists fled. In Italy’s bigger tourist cities, however, those days are a thing of the past. While April and October can still rightfully be called the “shoulder seasons,” you shouldn’t hear that and assume that both months will be relatively quiet - because you’ll be in for a rude awakening when you arrive and find the crowds still there.
To be fair, there are (generally speaking) fewer crowds in Italy in October than you will in June or July, but more people are catching on that the weather in Italy is still pretty doggone good (if not always reliably consistent) throughout most of the country in October, and the prices for things like hotels are starting to trend downwards then, and you’re more likely to find cheap flights as well. So it’s the perfect blend of decent weather and decent prices. Which is, of course, why it’s getting more popular to visit Italy in October.
You’ll find that the average temperature drops quite a bit from September to October (in some places by around 10 degrees F), so be sure you’re packing adequate clothing - layering is probably your best bet. And a waterproof or water-resistant outer layer is also a good idea, in case of sudden rainstorms. Of course, before you start packing you should consult a current weather forecast to make sure Italy’s not in the midst of an October heatwave where you’ll want your bikini instead of your umbrella!
October doesn’t have as many big festivals in Italy - at least not big ones that make major festival calendars - although you should always check with the tourist information office in the towns you’re visiting to see what’s going on when you’re there. A couple festivals in October worth mentioning are the Marino Wine Festival (in Lazio), which features fountains that spout wine instead of water, and the EuroChocolate festival in Perugia (in Umbria), which is perhaps Italy’s premier chocolate festival. When the weather is warm enough during the EuroChocolate festival, the entire town smells like chocolate - no kidding.
To learn more about some of the festivals that will be going on when you’re there, check out this Italy festival finder. And if you’re going to Perugia, bring me back some chocolate, won’t you?
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Having visited Venice, Florence and Rome in October, I agree that the weather is still very comfortable during that time. A few rain sprinkles here and there, but nothing that would slow you down, and temperatures were perfect for walking around and not getting over-heated or too chilled.