Siena & San Gimignano by Night: Tour with Dinner

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Discover the charms of Siena, San Gimignano, and the Chianti countryside on a small group evening tour. Avoid the crowds with an afternoon start, tour these popular Tuscan cities, and enjoy traditional regional dishes during dinner in the Chianti hills.


  • Visit Siena and San Gimignano, 2 of Tuscany’s gems
  • Take in stunning Chianti countryside views at sunset
  • Enjoy a typical Tuscan dinner along with a tasting of local wines
  • Small-group experience with a maximum of 16 people
  • Make the most of some free time in the hill-town of San Gimignano


Many centuries ago, Siena competed with Florence for power, wealth, and artistic beauty. Head out from Florence in a comfortable air-conditioned minivan with an English-speaking driver and tour leader for a full-day tour of Siena and the surrounding area. Enjoy a guided walking tour of the compact city center, and visit Piazza del Campo, the main central square, where the famous Palio horse race takes place every year. Take a walk through the quieter back streets as well, and learn about the contrade, the 17 medieval city districts that compete against each other in the Palio. The tour continues on to San Gimignano, famed for its medieval skyscrapers, high walls, and narrow streets that are characteristic of a typical Tuscan hill town. You’ll see a number of well-preserved tower houses and other centuries-old monuments. After some free time in San Gimignano, you’ll experience the sunset in the Tuscan hills and then enjoy a typical Tuscan dinner at a location in the Chianti countryside.  At the end of the tour, you’ll return to Florence in the comfort of the minivan.


Round-trip transportation in a comfortable minivan English-speaking driver/tour leader Guided walking tour of Siena Dinner at a Chianti countryside location Gelato in San Gimignano Guided visit of a winery with wine tasting

Important Information

  • Please inform the supplier in advance if you or anyone in your group have special requirements or impaired mobility, so that every effort can be made to accommodate these needs.

Easy cancellation

Cancel up to 24 hours in advance for a full refund


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