Siena, San Gimignano, Chianti Private Tour with Wine Tasting

Cultural & Theme Tours in Siena

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Tour description provided by Viator

An authentic and exclusive experience of Siena with the visit of its splendid old city center. Continue the journey back in time visiting San Gimignano with its famous towers. Have a delicious wine tasting at a small-scale production winery and discover an enchanting Chianti village.
ItineraryThis is a typical itinerary for this productStop At: Piazza del Campo, Siena, TuscanyMeet your private driver at your hotel for a beautiful excursion through the delightful hills of the Chianti countryside, with an ever-changing scenery of vineyards and olive trees. Upon arrival in Siena, your guide will bring you on a private tour of the old city centre: walking along the small medieval streets, admiring the splendid palaces and Piazza del Campo, one of the most beautiful in the world, where you will find the Palazzo del Comune (exterior). Free time for lunch (not included). Duration: 3 hoursPass By: Monteriggioni, Monteriggioni, TuscanyFrom Siena, your private driver will bring you through a panoramic road where to admire the vineyards and olive groves in the heart of the Chianti territory. Along the way you could also admire the ancient fortified hamlet of Monteriggioni, a small jewel built during the thirteenth century and embraced by its still intact walls. Stop At: Historic Centre of San Gimignano, San Gimignano, TuscanyYou reach then San Gimignano, another beautiful town, UNESCO world heritage, where you‘ll be given free time to visit the medieval town planning with the numerous and beautiful towers hence the name "Manhattan of the Middle Ages".Duration: 1 hourStop At: San Donato In Poggio, Tavarnelle Val di Pesa, TuscanyLeft San Gimignano you will reach a typical small-scale production winery located in the heart of the Chianti Classico area. Here, after a short walk in the ancient vineyards (where grapes are still handpicked by the passionate owner), you will visit the suggestive barrique room and taste 4 fantastic wines, sampling also locally produced zero food miles.Duration: 1 hourStop At: San Donato In Poggio, Tavarnelle Val di Pesa, TuscanyOn the way back to Florence, you will stop in San Donato in Poggio, an ancient settlement in a fortified castle dating back to the eleventh century, which maintains part of its walls and a stunning Romanesque parish church. Please note that the order of the visits may changeDuration: 20 minutes

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)
  • Entry/Admission - San Donato In Poggio

What’s not included

  • Food and drinks
  • Entrance fees to the monuments
  • Entry/Admission - Piazza del Campo
  • Entry/Admission - Historic Centre of San Gimignano
  • Entry/Admission - San Donato In Poggio


  • 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