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Tuscany trip planning feedback request

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Hi all, I am planning a trip in May to Tuscany, I have a rough plan and would appreciate any feedback and suggestions. We are mostly looking for scenery and photo ops. Good food is a big bonus too if its nearby. Not looking for museums.

Thursday: train to rome, visit Orvieto, pick up rental car to Pienza
Friday: Visit Montalcino and St. Antimo abbey, maybe visit some wine shops
Sat: cooking school in Tuscany in the morning, roam around Chianti in afternoon.
Sun: Visit Siena (will things be open on a sunday here?)
Monday: Visit Montepuciano and neighboring towns to the south (monticchiello, bagno vignoni, etc.)

Thoughts? too much or too little time planned for each day? too much of the same thing? is there a "better day" to visit one of the towns?

BTW, does anyone know what is the holiday of saint of Castelnuovo dell’ Abate? I heard about it from a winery, but couldn't find much info about where/what it is on the internet.

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