Tuscany/North Italy End of September vs. Beginning of October

I would explore the week prior; none the cities you plan on going to are in Tuscany.
So based on what you want to see in a week prior I would fly into Milan take the train to the Varenna (that is Lake Como area located in the region of Lombardy) then go to Bologna to Verona to Florence (Tuscany).

Tuscany surrounds Florence, all the cities you mentioned are northern Italy. September is right in the middle of grape harvest so I'd recommend going before the wedding and maybe look into an agriturismo where you can participate in the harvest. There are a lot of beautiful hill towns around Florence and throughout Tuscany to explore, Siena, San Gimignano, Montepulciano, Pisa.

If you're traveling between Milan and Bologna, you may want to consider a stop in Parma, home of great ham and parmesan cheese.

Thank you both for the great advice!

I guess we'll want to split our time between Tuscany (proper) and Northern Italy as well. I've updated the topic name to indicate that.
Taking that into account would it still make sense to aim for last week of September or push it to beginning of October? I'm guessing weather won't differ much within that short of a span but hotels might be cheaper into October possibly?

As mentioned, this will be in the middle of harvest season. There are lots of harvest festivals. I suggest you do some research and find one that sounds appealing and schedule around it.

hey vadim
as doug mentions it is harvest season. lots of wine festivals everywhere. if you happen to be near lake garda, they have their annual bardolino wine festival october 3 - 7 in bardolino on the lake. we had a fabulous time, eat drink and be merry.
it will be busy and some places still crowded, go with the flow. if plan A doesn't work go to plan B. do research of the areas you want to be, if you're driving check rome2rio.com for travel times (add more time) and maps of city to city, if you're coming from north america, get your IDP from AAA/CAA for driving in italy, read the laws, signs and rules of the roads. have a great and fun time.
aloha

Early October wasn’t less crowded when we visited Florence as it still is a popular time to visit. . However, my main reason for going in October is that it will be cooler . We have dealt with high heat and humidity in September.

Thanks all for the great info!

Sounds like the benefits of doing beginning of October slightly outweigh September. We'll be sure to check out the festival schedules, as suggested, to see if anything in particular sways us one way or the other.

hey vadim
festivals-of-tuscany.com

lots of festivals listed by the month.
discovertuscany.com under things to do click events calendar
ask host of place you are staying, stop into tourism kiosk in piazzas of cities for info.
have fun and enjoy
aloha