Meet your private driver at your Florence hotel for a full-day tour through the Chianti countryside, a stunning Italian wine region known for its spectacular array of vineyards and olive groves. Once reaching Siena, you'll embark on a guided walk through the city's old town, exploring its medieval streets, marveling at its palaces and learning about Siena's varied history as you go. While here, you'll enjoy an opportunity to visit its 13th-century cathedral, home to the Libreria Piccolomini a fresco-covered hall originally built to house the books of Pope Pius III.
After some free time for lunch (own expense), you'll rejoin with your group for a drive through the heart of the Chianti territory, passing by the ancient fortified hamlet of Monteriggioni en route to San Gimignano. This UNESCO-listed World Heritage Site is known for its many distinct medieval features, including the Torre Grossa or Great Tower and its Duomo di San Gimignano. Set out on your own to discover this picturesque hill town known as the "Manhattan of the Middle Ages, before meeting back up for a visit to a typical small-scale production winery in the heart of the Chianti Classico area. Walk through its ancient vineyards (where the owner still handpicks grapes) on your way to the winery's barrique room, where you'll get to taste four different wines paired with an array of locally sourced delicacies.
Your return trip to Florence includes a stop in San Donato in Poggio, an 11th-century fortified settlement that has maintained part of its walls and is home to an exquisite Romanesque parish church.
Please note: On Sundays and National Holidays, Siena's cathedral is closed to the public; it is replaced with the Basilica of San Domenico.