Florence: Siena, San Gimignano, & Chianti Wine Tasting

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Explore the charming towns of Siena and San Gimignano in Tuscany on this guided tour from Florence. Taste chianti wines and savor a sumptuous vineyard lunch at a beautiful, family-run vineyard.


  • Travel to three stunning cities in Tuscany.
  • Walk through Siena and Piazza del Campo.
  • Visit Chanti for a seasonal lunch with wine.
  • Indulge in a wine tasting & tour of a Chianti vineyard.
  • Stop in San Gimignano with free time to shop and explore.


Your day starts in Central Florence where you’ll meet your small group of no more than 14 people and an expert tour guide. Then you’ll hop into private transportation and be spirited out of the city and over to Siena. On the way out of the city, we'll pass the best panoramic viewpoint of Florence and stop to take a few pictures. A little over an hour drive away, Siena is one of the best-preserved examples of medieval Italian architecture in the world. Spared bombing in World War II, this time capsule of ancient, precarious-looking buildings is home to the Palio, one of the greatest and most dangerous horse races in the world. Your guide will immerse you in the unique history and culture of Siena as you explore its narrow streets and admire the breathtaking Siena Cathedral from the outside. Walking the hills of Tuscan towns will make you hungry and thirsty so your next stop is an authentic Italian family farm in Chianti where you will have a behind-the-scenes tour of the vineyards, winery, and wine cellars before sitting down for a sumptuous, all-inclusive lunch made from local, seasonal ingredients. Your meal will be paired with Chianti wines specially selected to perfectly complement the flavors of each dish. After indulging your taste buds, you'll stop at San Gimignano, a town of such unique architectural beauty it has been designated a UNESCO World Heritage Site. Shop for Tuscan culinary delicacies in the rustic, winding streets, or learn about the architectural marvels of the famous medieval tower houses that punctuate the city like sentinels of times long past.


Expert English-speaking guide Designated professional driver Air-conditioned transport Guided walking tour of Siena Guided walking tour of San Gimignano Gourmet lunch Wine tasting in Chianti

Important Information

  • This is a walking tour. Guests should be able to walk at a moderate pace without difficulty.
  • The tour meeting time is 15 minutes before the start time. No refunds can be provided for late arrivals or no-shows.
  • Those with dietary restrictions should contact us after booking the tour so we can arrange your lunch.
  • If you are traveling with a small child, please contact the activity provider before booking to confirm there's enough room in the vehicle.
  • Tickets for the Siena Cathedral are not included in the tour price. If you wish to visit the Cathedral, your guide will assist you. The Cathedral is closed on Sundays and for certain holy days.
  • In order to take you directly into the city center, we utilize small luxury minivans. Your guide may need to split time between vehicles on groups larger than 8.
  • Walks / Devour complies with all local government regulations. Please refer to local government guidelines for the most up-to-date information.

Easy cancellation

Cancel up to 24 hours in advance for a full refund


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