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Milan Bellagio and Tuscany

Hi Friends,
I'm early planning a trip next year - late September to early October. We (2 couples mid 60's healthy and fit) plan to fly into Milan.
I was thinking
Milan 2 nights Rent a car and drive to
Bellagio 3 nights Drive car back to Train station bullet train to
Florence 3 nights Rent a car for the next 7 nights
San Gimignano 4 nights
Montepulciano 3 nights return car to Florence airport to fly back

This is a rough sketch. We already booked Mongepulciano VRBO and intend to stay on a vineyard in San Gimigano.

But I'm not sure if Bellagio makes sense. I know it's glorious, but October may be chilly. Or maybe 2 nights is enough. Bergamo also sounds interesting.
We're very excited about wine tasting in Tuscany.

Any thoughts are most welcome and highly appreciated.
Cheers,
Ellen

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