Private Tour: Siena and San Gimignano with Wine Tasting and Chianti Village Visit

Day Trips & Excursions in Siena

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Tour description provided by Viator

Explore the Chianti countryside on a private full-day tour from Florence, with visits to Siena, San Gimignano and a traditional village. Delve back in time with a guided stroll through Siena's old town, and step inside its storied cathedral ― home to the magnificent Libreria Piccolomini. After lunch (own expense) enjoy some free time in the UNESCO listed town of San Gimignano, then set out for a local winery for a tasting of local vino varietals. See the medieval village of San Donato in Poggio on your return to Florence.
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.

What’s included

  • Hotel pickup and drop-off
  • Private vehicle: Luxury Sedan (1-3 pax) or Luxury Minivan (4-8 pax)
  • English-speaking driver
  • Wine tasting (4 varietals)
  • Stops in Siena, San Gimignano and San Donato in Poggio
  • private local guide in Siena (approx. 2 hours)
  • Entrance fees: Siena Cathedral and Libreria Piccolomini

What’s not included

  • Food and drinks


  • Enjoy a day away from the hustle and bustle of the city
  • Free hotel pickup and drop-off included
  • Informative, friendly and professional guide
  • Private guide for a more personalized experience
  • Instant Confirmation