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San Gimignano, Siena, Monteriggioni, Chianti: Day Trip with Lunch & Wine Tasting

Instant confirmation E-Voucher

Activity Schedule

  • When does it run?

    April to October: English - every day; Spanish - Monday,Wednesday,Thursday, Friday,Saturday - French - Tuesday, Sunday

    November to March: English - Monday, Wednesday, Friday and Saturday; Spanish - Monday,Wednesday, Friday; French – Saturday

  • Duration

    11 hours (approx)

  • Start time


  • Meeting Point

    Make your way to Piazzale Montelungo, Florence - at the end of the ramp connecting with the train station.

    An Assistant waits for you wearing blue clothing with Caf Tour and Gray Line Logos.

  • Ending Point

    Same as starting point

Key Highlights

  • Smartphone voucher accepted – No need to print!
  • Visit two stunning UNESCO World Heritage Sites and go back to the Middle Ages
  • Discover Siena Top Sights with a local Professional Guide
  • Wonderful views of Tuscan rolling hills and visit of two medieval Villages in the Chianti countryside
  • Enjoy the Visit to the cellars and vineyards together with a typical Lunch in a cozy Chianti Winery
  • Taste 3 different Chianti Wines, Balsamic vinegar and


Full day Tour in the heart of Tuscany region: San Gimignano - the "Manhattan of the Middle Ages", the most famous and picturesque Tuscan hill village together with the unique experience of Siena and its traditions, thanks to the comprehensive guided tour of the stunning old town. The picturesque Monteriggioni Hamlet and the relaxing stop at a Chianti Winery for a typical Lunch which includes the guided Tasting of 3 different Wines and “vin santo”.

Visit the charming San Gimignano, the famous walled town located on a hilltop, renowned for its tall towers, wonderful frescoes and many other valuable works of art. Explore the historical center with the tour leader, where you will have around 2 hours of free time for a fascinating discovery.

Next, we go to San Gimignano, the charming historical hamlet of Monteriggioni (*), an amazing small medieval village which remained standing to this day.

From Monteriggioni, crossing the gently Chianti rolling hills, visit a cozy Winery, where you can relax and enjoy the fantastic world of Chianti with its wine and typical products: tasting of three fine wines and balsamic vinegar followed by a Chianti style lunch: 3 course with “zero food miles” products which ends with "cantucci e vin santo".

Once in Siena, your guide will lead you on a guided tour of the historic center, starting from the famous Basilica of San Domenico, a jewel of Renaissance art built in the 13th century. Explore the narrow medieval streets of the city, flanked by splendid palaces and historic shops, passing through Piazza del Campo, of which the Palazzo Pubblico (Town Hall) is the focal point. See the spectacular Cathedral of the 12th century (inside visit if option selected), take in the magnificent architecture and the splendor of the polychrome marbles.

Spend time exploring on your own before the return to Florence in the evening.

Please note that the order of the visits may change.


A multilingual tour escort will accompany you throughout this trip. As you drive through the beautiful Italian countryside, your tour escort will keep up a running commentary about Italian history, art, and landscape.

Your first stop during the trip will be Siena, a small town in the heart of Tuscany. Siena is considered to be one of the best preserved medieval towns in Italy. You'll be free to explore the town at leisure; make sure to see Siena's beautiful Cathedral, and take a look around the historic Piazza del Campo, said to be one of the most beautiful squares in Europe. Admire the charming architectural styles that you see in Siena.

After spending approximately 4 and a half hours in charming Siena, you'll head to San Gimignano, a hilltop Tuscan town. The city is surrounded by walls, and is famous for its medieval architecture and tall buildings. Some of the city's most beautiful works are its churches, especially the Collegiate Church and the Church of Saint Augustine, which hold works by Renaissance artists.

Leisure time in San Gimignano is approximately 2 hours, after which you'll board the coach to return to Florence. The trip should return around 7:00pm.


  • Caf Tour’s Team Assistance at the meeting point
    • Transport by air-conditioned Coach with Wi-Fi on board
    • Licensed Tour Escort (English, Spanish, French-speaking)
    • Visit to the cellars, vineyards and 3 course typical Tuscan lunch in a Chianti Winery
    • Tasting of three different Chianti Wines, balsamic vinegar plus “vin santo”
    • If Option Selected: Guided Visit in Siena with Professional local Guide (April to October monolingual Tour)
    • If Option Selected: further Visit, led by Professional local Guide, inside Siena Cathedral and Libreria Piccolomini with skip-the-line Ticket


    • Meals Entrances to any museums, galleries, etc.
    • Hotel pick-up and drop-off

    Useful downloads

    Please note

    Voucher Information : No need to print! You can show your voucher on your smartphone or other device.

    Please call the local activity operator at least 24 hours prior to the start of the tour to confirm all details.

    Should you make a booking and your tour do not operate as minimum numbers are not met, tour will be offered on alternate date; if this is not possible you will be offered a full refund.

    The time of departure and return might be subject to delays due to the traffic circulation restriction.

    For small groups of up to 8, the Tour escort could be replaced with an English speaking driver-guide.

    On Sundays and National Holidays, the Cathedral is closed to the public.  

    Piazzale Montelungo can be easily reached as usual from Piazza della Stazione (Station Square) through various access routes.

    Customer Reviews

    • Reuben Judah
      Excellent tour

      Excellent tour. We especially enjoyed our visit to Greve and the Chianti vineyard...

      United Kingdom 09/13/2017

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