re: Last minute recs for Florence, Montepulciano, Siena (and kind of Rome)

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and renting e-bikes in Montepulciano to bike around to some small towns

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Hilly narrow two lane roads around there. Be safe.

Go to Radda and eat lunch at La Botta di Bacco. It's a Michelin Star restaurant and if you're lucky the chef /owner will take you ordere, cook for you and serve you. I'd sit at this table.