Meet your guide at Piazzale Montelungo Bus Terminal, a short walk from Santa Maria Novella train station. Board a comfortable coach and head south through the Tuscan hills toward Val d'Orcia, a journey of approximately two hours during which your guide shares background on the valley's history and landscape.

Your first stop is Montalcino, a compact hilltop town perched above vineyards producing some of Italy's most celebrated wines. A local producer leads the group through the winery, explaining the Brunello production process before guiding a tasting of the estate's finest bottles.

Arrive in Pienza, rebuilt in the 15th century according to Renaissance ideals at the order of Pope Pius II. The town's cathedral, Palazzo Piccolomini, and sweeping panoramas over the Orcia Valley reward leisurely exploration, and the streets here are lined with local food and craft shops.

The coach travels through open countryside, pausing near the Chapel of Madonna di Vitaleta, one of the most photographed subjects in Tuscany. Your guide identifies the cypress-lined valley that served as the gladiator's home in Ridley Scott's film, providing context for the location's cinematic history.

The final stop is Montepulciano, a stately hilltop town of Renaissance palaces and imposing churches, and the setting for the Twilight film New Moon. A guided visit to a historic underground wine cellar is followed by a tasting of Vino Nobile accompanied by locally produced Pecorino cheese and light snacks.

After time for last-minute shopping, the coach departs Montepulciano and returns to Florence, arriving in the early evening. Drop-off is at the original meeting point near Santa Maria Novella.