San Gimignano, Chianti, and Montalcino Day Trip from Siena
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4.60 (108)
11 hours

11 hours




Start with a 7:30am or 8:30am hotel pickup, depending on the time of year. As the sights of Siena slip into the distance, you’ll notice the landscape turn into the undulating hills of Tuscany.

Your first stop in the region is the beloved hill town of San Gimignano, a UNESCO World Heritage Site. Enjoy free time here to wander the streets of its historical center, gazing at the medieval architecture, towers, piazzas, and artisan shops. San Gimignano produces the renowned vernaccia wine, and you’ll find plenty of enoteche (wine shops) around the streets.

Then, travel into the Val d’Orcia region of Tuscany where the winemaking village of Montalcino awaits. Next, you’ll head to the historic fortress town of Monteriggioni. Stop at a winery for lunch and a wine tasting. Savor a light meal of local cheese and salami, paired with Chianti wine.

Taste the esteemed Brunello di Montalcino wine, and learn about the town’s winemaking traditions.

Relax on the journey back to Siena, and finish your day trip with a hotel drop-off.

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myTour in Italy



  • Explore San Gimignano by foot and admire its medieval towers
  • Stop for lunch and Chianti wine at a Montalcino winery
  • Travel through the idyllic Val d’Orcia region
  • A small group means a more personalized experience
  • Itinerary

    • San Gimignano 1300

      Free time in San Gimignano

      1 hour
    • Collegiata di Santa Maria Assunta - Duomo di San Gimignano

      During your free time opt to visit the Cathedral of San Gimignano

      15 minutes
    • Piazza della Cisterna

      Free time in San Gimignano

      15 minutes
    • Palazzo Pubblico e Torre Grossa

      Free time in San Gimignano

      15 minutes
    • Chianti Road

      Lunch and wine tasting in a local winery in Montalcino

      1 hour
      Admission Included
    • Fortezza di Montalcino

      Free time in Montalcino

      1 hour
    • San Filippo Montalcino

      Free time in Montalcino

    • Val d'Orcia

      Spend some time in the stunning Orcia Valley

      1 hour
    Meeting Point Map



    Piazza Antonio Gramsci, 53100 Siena SI, Italy

    Open Google Map


    • Expert multilingual escorts
    • sliced cured meats and typical salami
    • Wine tasting and Lunch consisting of typical Tuscan dishes
    • Travel by minivan with air conditioning for a maximum of 8 people


    • Gratuities

    Additional Information

    • Infants and small children can ride in a pram or stroller
    • Public transportation options are available nearby
    • Specialized infant seats are available
    • Suitable for all physical fitness levels
    • Customers must be able to climb and descend stairs.
    • Vegetarian option is available for lunch, please advise any specific dietary requirements at time of booking

    Guide Languages

    • English

    • Spanish

    • Italian

    Cancellation Policy

    • A full refund will apply if you cancel more than a day before the activity start time.

    • No refund is possible if you cancel less than a day before the activity start time.