Start Time


End Time



11 Hours

Customer Support

08:00am 05.30pm (Mon to Sat)

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

Your memorable journey starts with the charming San Gimignano, world famous walled town located on a hilltop, which remained intact through the centuries, renowned for its tall towers, wonderful frescoes and many other valuable works of art: here the tour leader will lead you to the historical center, where you will have around 2 hours of free time for a fascinating discovery. A short distance from San Gimignano you will visit the charming historical hamlet of Monteriggioni*, an amazing small medieval village enclosed by its famous walls, which remained standing to this day: free time for inside visit. From Monteriggioni, crossing the gently Chianti rolling hills, a short ride will take you to 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". Later on, getting to Siena, you will meet your professional local guide who will lead you on a comprehensive guided tour of the historic center, starting from the famous Basilica of San Domenico, a jewel of Renaissance art built in the 13th century and dedicated to St. Catherine of Siena, of which preserves a relic. Then strolling along 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, you will get to the spectacular Cathedral of the 12th century, of which you can admire the magnificent architecture and the splendor of the polychrome marbles. You will experience an amazing inside Guided Visit of the famous Siena Cathedral (if option selected), together with its Libreria Piccolomini, to discover the beauty of its treasures and works of art. You will visit the not-to-be-missed floor (during the opening period), decorated with the art of mosaics to create storytelling masterpieces, St. John the Baptist by Donatello, the rose window by Duccio di Buoninsegna, the marble pulpit by Nicola Pisano, the Library which kept a rich collection of manuscripts. You will also have some free time to end your perfect day enjoying the unique atmosphere of this amazing city, before the return to Florence in the evening. Please note that the order of the visits may change (*) From November to March, the itinerary does not include the stop at Monteriggion and the return to Florence is approx 30 minutes earlier


  • Visit Two stunning UNESCO World Heritage Sites
  • Siena: exclusive opening of intimate and secret sights and the Cathedral
  • Wonderful views of Tuscan rolling hills and Chianti countryside
  • Enjoy the Visit to the cellars and vinejards together with a typical Lunch in a cozy Chianti Winery
  • Taste three excellent Chianti wines
  • Picturesque, Medieval village famous for its colors and charm

Pickup instructions

• Check-in and Meeting Point: Tour departs at 08:00 from Piazzale Montelungo, at the end of the ramp connecting with the train station. Please reach the meeting point 15 minutes before. An assistant will be waiting for you wearing blue clothing with CAF Tour - Gray Line logos

Voucher redemption instructions

• Cancellation Policy: No penalty for cancellations up to 48 hours in advance of the schedule departure time. For cancellation made less than 48 hours before the tour departure and in case of no show, 100% of penalty will be applied. • Check-in and Meeting Point: Tour departs at 08:00 from Piazzale Montelungo, at the end of the ramp connecting with the train station. Please reach the meeting point 15 minutes before. An assistant will be waiting for you wearing blue clothing with CAF Tour - Gray Line logos. All participants must wear an FFP2 mask • Additional Info: o Minimum numbers apply. There is a possibility of cancellation after confirmation if the minimum number of passengers is not reached. In the event of this occurring, you will be offered another date or an alternative Tour or full refund. o The local guide service could be provided in two languages. The tour escort service is multilingual. o It is recommended that participants wear comfortable shoes and appropriate clothes to visit museums or places of worship. o For additional information please check our Terms & Conditions at the address https://graylineflorence.com/terms/. • Our Contacts: Agency address: via dei Tavolini 15red - 50122 Firenze - Phone 39 055 29.55.72 or 39 055 28.32.00 - Whatsapp: 39 3458025842 - email address: tours@caftours.com Opening times: Monday to Friday from 10:30am to 07:00pm; on Saturday and Sunday from 10:00am to 07:00pm


  • Caf Tour’s Staff Assistance at the meeting point
  • Transport by air-conditioned Coach with Wi-Fi on board
  • Licensed Tour Escort
  • 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”
  • Guided Visit in Siena led by Professional local Guide
  • Cathedral and Libreria Piccolomini inside visit & skip-the-line Ticket (if option selected)
  • Optional Gratuities
  • Hotel pick-up and drop-off

Suitable for

  • Solo travellers
  • couples
  • children
  • groups
  • students
  • business trip
  • wheelchair

Additional Information

Has Hotel product Type:
No hotel product type loaded
Product Type:
Tailor made
Tour Leader Type:
Independent / self drive


To be updated