Italy… I don’t know where to even start!
It was an amazing experience. Unlike anything or anywhere I’d ever been. Would I go again? In a heartbeat.
And I would definitely go in February, March, October or November. As a Canadian, I like my space. I don’t like crowds and I’m simply not accustomed to waiting more than 15 minutes in any line.
Even the locals in Florence told me, that they flee the cities in July and August. The cities are too hot and far too crowded. The place to be is by the sea. And I got the impression that tourists are not completely welcome at their seaside hideaways, some of the last undeveloped tourist areas.
September is a lovely month, for weather. But, it’s also harvest. Their agricultural economy depends on the grape harvest, which is then followed by the olive harvest late September, early October. Their culture and livelihood are so intertwined with this annual ritual that I wouldn’t want to get in the way as a tourist wanting to tour wineries.
In late February, we had lovely weather, about 15C most days. I was comfortable in a light jacket, and with a scarf in the mornings.
As far as tourist sites, like the Leaning Tower of Pisa, the wait was less than 15 minutes and you could just walk up and purchase a ticket at the desk. In tourist season (April-Sept) you would need to buy tickets on-line, in advance and attend at your scheduled date and time to avoid waiting 2-3 hours in the walk up line. You have likely read this several places if you are already researching a trip to Italy or Europe
Flight deals can be had, especially in the low season. If you choose to go to Italy in October through February, you can watch for airfares as low as $650 on sale. High season, you would budget for $900 or more per ticket. (Taxes in, return trip from YWG)