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Val d'Orcia help (BOB THE NAVIGATOR, STU, EXPERTS PLEASE HELP!)

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Looking for the perfect hill town south of Florence to stay for 2 nights. Our #1 choice right now is La Laconda di San Francesco in Montepulciano but are up for recommendations.

- We'd also like to do a private wine tour in the region so looking for recommendations there as well. Is Castello Banfi a tourist trap?

- Can you please rank the towns of Val d'Orcia in terms of food/wine/overall, is Montalcino a better choice than Montepulciano, etc.?

- Our other option is to stay in Chianti but I hear that is too civilized vs. Val d'Orcia.

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