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Situated in a privileged position in front of the Val d’Orcia, this town went by the name “Republic of Siena in Montalcino” when the Sienese supporters were still fighting against the Florentines, even though Siena was already in Florence’s hands.
Montalcino is renowned for its Brunello wine, yet there are other delightful and more affordable red wines to try such as the Rosso di Montalcino. If you are not interested in wine Montalcino with its steep narrow streets is still a  wonderful place to wander.
Since wine is of main importance the town is filled with enoteche. Bottles of Brunello range from €20 to 105 or €5,000 for a 1940 vintage so you can pick whichever is in your price range to try out.