When to Travel

Our preference is mid Sept through Oct. The weather is generally better (drier) and the tourist crowd is less. By end of Oct it can be getting cooler with shorter days but still a good time.

September is hot to start... later is better. October is usually delightful, although we've certainly encountered fog and rain.... Start in Venezia and move south leaving from Rome. No reason to go to Milano on a first trip, iMHO, unless it is your arrival or departure airport and you really want to see the Last Supper.

kj,

I'd also recommend travel in the mid-September to mid-October range. I've always found the weather to be great at that time of year, although of course no guarantees there won't be some rain.

All my trips to Italy have been in late September/early October & the weather has been nice.

On our last trip we had a couple of rainy days but that didn't stop us. We borrowed an umbrella from our hotel
or you can buy an inexpensive one from the street vendors that pop- up at the first drop of rain!

I agree with Laurel:

Start in Venezia and move south leaving from Rome.

Buy open-jaw flight tickets so you don't have to backtrack.

How long is your trip?

Happy planning!

How about April? I'm thinking of planning a trip around that time.

For a fall trip, other than weather, you may find prices on flights and hotels decrease as the days get shorter. So do the number of tourists.

As for April, there've been a couple of threads in the last few days about the pitfalls of April - mainly Easter week (in 2015 Easter Sunday is April 5) and April 25 to May 1 (both dates are major holidays, so there is a lot of local tourism during that week. For more information, look for those threads.

Eg -- on this site it is best to start a new question rather than hijacking an existing question because the OP will now receive notice of an answer to their question when it is really an answer to your question.

Our experience with April is that it tends to be cooler and rainy. Of course, that depends a little bit on where you are but the Spring is a little more iffy.

Just got back from a 10 day trip that included Rome, Florence/Tuscany, Venice, and Milan a few days ago.

There weren't as many tourists as I imagined, which was great. I think November is a great time to go, but doing it again, I would probably go in October. Venice, Florence, and Milan weren't crowded at all. You could walk into any site/museum and if there was a line at anything, it was 5 minutes max. The only place I encountered some overcrowding was in Rome. If it's crowded during November, I can't even imagine what it's like during the Summer.

The only thing you would have to worry about going in the Fall is the weather. I was told that this year it wasn't as cold as it normally gets. Temperatures ranged from high 50s to the low 70s throughout the trip. The days were dark until about 900ish and the sun set around 500ish. It wasn't too cold, but I did get about 2 days of rain, which wasn't too bad.

Some of the sites were under construction during this time of year as well, so watch out for that. For Tuscany, some wine tours were only available from March-October, so I missed out on that. The only wine tour for Florence/Tuscany I could find was this one http://www.tuscanwinetime.com/, which was actually pretty great; but there wasn't a lot of selection.

Another vote for a mid-Sept start. We've almost always been blessed with lovely weather (2 days rain out of 23 one trip - and that was only for an afternoon). This year we went to Italy (Rome/Amalfi/Venice) in early Sept - wow - the heat was crazy. Venice was great because we got there in the middle of the month. Our other 3 trips over all started mid-Sept. I think getting into Nov that rain is a lot more predominant (judging from news reports I've seen of flooding in some areas - usually seems to start mid -Oct). Plus mid-Sept you get a little longer daylight hours, warmer temps...

I did a trip in April 2009, for 3 weeks, and my wife & I thought it was perfect. Cool/cold (we are Floridians) in the morning and better throughout the day. Perfect was tons of walking/hiking which is what we did for much of the trip. Started in Milan, to see the Last Supper & Cathedral, then slowly moving south through Venice, Tuscany & Florence, Cinque Terre, Sorrento (seeing Mt Vesuvius, Herculaneum, Paestum, Amalfi Coast), then up to Rome and flying out of there. Perfect....We are going back soon and doing a cruise and then hiking the Dolomites per Laurel's suggestion :)

I travelled to Italy this year from 10/22 thru 11/07. The weather was so perfect! I took an umbrella figuring I would encounter lots of rain, and only had to use it one day during the entire trip. It was such an ideal time to go, fewer tourists, cheaper flights and hotel rooms, etc. My previous travel to Italy was in May, and though it was pretty nice I much preferred Fall.