Meet a dedicated guide at Santa Maria Novella station in Florence at 9am (for a full day trip). Climb into the private vehicle and set off for the rolling countryside of Tuscany. Make your first stop in Montalcino, after a stop to a winery, the town of Brunello with winding streets and historic buildings. Have a look around the town's and taste some local wine in a wine bar and visit the castle, which gives way to photo-worthy views over the surrounding countryside.

Return to the main road and move on to Montepulciano, where you will have some free time to look around on your own its amazing city center and the church of San Biagio. After spending time in Montepulciano, tasting Il Nobile di Montepulciano, move on to have lunch in a restaurant.

In the afternoon, visit Chianti and taste some wine in a winery. Descend down the hill to Greve, where you will have some free time to look around on your own. If you are there on a Saturday, be sure to hit up the town's weekend market for some tastes of Tuscany and unique souvenirs. If you are interested, the guide can set up a wine or olive oil tasting in town (optional, additional expense) before head out of town to visit a classic Tuscan winery. Once arriving at the winery, meet an onsite guide to learn about the cultivation of the local Sangiovese grapes and taste some wonderful wines. Return to the original departure point for the drop-off after 10 hours of exploring the Chianti and Sienese region.