I already know July and August are packed and hot, so I’m ruling those out. For the cities and Tuscany, which stretch of shoulder season gives the best balance of decent weather, open sights and fewer crowds - late April and May, or September into October? After real experience, not the generic ‘spring or fall’.
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I just came from 6 weeks in Italy and the crowds were horrible in late May early June. Most people I talked to who live there say to go in January or February. This was my 3rd time visiting over a 45 year period and the crowds were so much worse!
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For Tuscany specifically, I’d lean toward late September into early October. Since so much of the appeal there is the countryside, wine, food, hill towns and architecture, you don’t really need peak summer weather to enjoy it. Cooler temperatures honestly sound like a bonus when you’re spending entire days walking around Florence or exploring towns in Tuscany anyway. It’s also harvest season, which I think would make wine country especially interesting to experience.
@lesley , which towns are you considering in Tuscany besides Florence? I’m curious whether you’re planning more of a city trip or a countryside one.
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From our experience in the past 5-7 years most popular sites tend to be crowded except for Jan-Feb and perhaps Nov-Dec. For shoulder season, late March and late October stand the best chances.
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I vote September-October! When I went it definitely did not feel as busy as I expected, the weather was great and everything we wanted to experience was available to us. Plus we headed North to South so we kept the warm days and cool nights even getting into late October.
As an Italian, I’m definitely team September into October 
April and even May can still be a bit too fresh and unpredictable, especially if you want to spend a lot of time outside. September, on the other hand, still feels like summer in a lot of Italy, just without the worst of the heat.
For me, the sweet spot would be late September to mid October. You still get beautiful days, but walking around Florence or exploring Tuscany is so much nicer when it’s not 35°C and completely packed.
And Tuscany in autumn just fits. Food, wine, harvest season, cooler evenings… I’d personally choose that over April or May.