From Florence: San Gimignano, Siena, and Chianti Wine Tour

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Join a full-day tour from Florence and spend the day exploring villages and wine regions in the heart of the Tuscan countryside. Visit San Gimignano and the medieval towns of Siena and Monteriggioni.


  • Escape the bustle of Florence and explore the beautiful Tuscan countryside
  • Drive through the rolling hills of the Val D’Elsa in air-conditioned coaches
  • Visit the medieval town of San Gimignano, home to Vernaccia wine and saffron
  • Explore the immaculate town of Siena, world-renowned for its Palio horse race
  • Visit a splendid Chianti estate and take part in two exclusive wine tastings


Explore the heart of beautiful Tuscany on a full-day tour of the towns of San Gimignano, Siena and Monteriggioni, then discover the bucolic wine region of Chianti. Reach easily our meeting point by taking the T1.3 tram heading to Villa Costanza. Depart from Florence by an air-conditioned bus to your first stop, the UNESCO World Heritage Site of San Gimignano. Discover Siena, the city of Palio horse-race and its enchanting architectural styles, including the Cathedral in Piazza del Duomo and Palazzo Comunale (Municipal Building) in Piazza del Campo. Piazza del Campo is famous shell-shaped square provides the stage for the thrilling Palio horse race, run twice every summer. Afterward, head out to a unique location in the Chianti countryside to enjoy a wine tasting. Once you hop off the bus, be guided around a splendid winery. Get introduced to the estate's fascinating history and background. Head inside the cellars to learn the secrets of Chianti winemaking together with the local host. Then enjoy a delicious wine tasting of Chianti Classico. Once the winery stop is over, the tour will end with a visit to the marvelous Monteriggioni castle, a medieval fortress that is really well-preserved. You may also recognize it from the Assassin's Creed video game series. Last but not least, enjoy one of the most splendid examples of an Italian medieval town, San Gimignano. Distinguished by its famous towering skyline, San Gimignano stands along the Via Francigena on the hills of the Upper Val D’Elsa. Get acquainted with the Tuscan environment with the town’s Vernaccia di San Gimignano wine, saffron, and Santa Fina pottery. Take your free time to stroll through the town on your own and see its beautiful squares, architecture, churches, and side streets.


Air-conditioned bus or minivan Multilingual guide Guided tour of Siena (if option chosen) Free time in San Gimignano Visit to the medieval village of Monteriggioni Wine tastings Guided visit to a Chianti estate

Important Information

  • This tour will be conducted in multiple languages at the same time, but only English is guaranteed for the guided tour of Siena The tour itinerary may change according to the season and unforeseen circumstances Customers must be able to climb and descend stairs You can easily reach our meeting point by taking the T1.3 tram line

Easy cancellation

Cancel up to 24 hours in advance for a full refund


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