Shopping and Dining: Just outside your door, in the small village of Montefollonico, there is a small grocery shop, a café bar and three restaurants within a 100 yard walk. The grocer is open Monday through Saturday until 7:30 pm, and the proprietor often makes local dishes or baked goods - on Wednesdays, she makes take away pizza. More dining and shopping options are available in Montepulciano which has a COOP supermarket.
Not To Be Missed: The cheese maker's farms along the road to Pienza, known for its herb enriched, pecorino romano cheese made from sheep's milk.
Public Transportation: Chiusi, 35 minutes away, is on a primary line with high speed trains to Florence or to Rome in 90 minutes.
Golf: Golf Club Valdichiana, a 25 minute drive, is open year round. Closed on Wednesday.
Tennis: Public courts are available in Montefollonico. The courts are open 7 days a week and closed in the winter season.
Thermal Baths: The Terme di Chianciano, 15 minutes by car, is a wellness center offering European treatments centered around medicinal cures. This center is known for its Sensorial Salon, a self guided program with 12 stations including hydromassage pools, sauna and Turkish bath, aromatherapy showers, music therapy and thermal muds. Bagno Vignoni, a tiny medieval village is a 30 minute drive with a thermal spring water pool in the village center commissioned by the Medici family.
- May: For the last Sunday, during the "Open Cellars", vintners in Montalcino open their doors to the public for wine tastings.
- June: Festa del Barbarossa takes place in San Quirico d'Orcia on the third weekend with a medieval costume procession through the village ending at the Horti Leonini Italianate gardens where neighborhoods compete in archery and flag throwing.
- August: In Pienza, August 14th is celebrated as the night of the Assumption with historic buildings opening their courtyards, and a torch light procession ends with fireworks. During the last week, Montepulciano hosts Bravio delle Botti, a race between the 8 contrada or neighborhoods with 50 pound wine barrels carried through the historic center. Dinners and games take place all week long.
- September: Pienza's Fiera del Cacio or cheese festival takes place on the first Sunday.
- November: The white truffle festival in San Giovanni d'Asso, 30 minutes away takes place on the 2nd and 3rd weekends.
- December: San Quirico hosts an olive oil festival on the first weekend with producers setting up stands to introduce their new vintage, live music and olive oil massages given in Palazzo Chigi.
Open Air Markets: Morning markets are held on Tuesdays in Chiusi, on Wednesdays in Chianciano Terme, on Thursdays in Montepulciano and on Fridays in Pienza and Montalcino.