San Gimignano and Siena Day Trip: Explore Tuscan Villages With a Chianti Wine Tasting

Embark on a full-day tour to San Gimignano and Siena, exploring the charming Tuscan villages and indulging in a Chianti wine tasting. Discover the medieval beauty of San Gimignano, immerse yourself in the traditions of Siena, and enjoy a delicious lunch at a Chianti winery.

Duration: 11 hours
Cancellation: 1 day learn more
Highlights
  • San Gimignano - 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.
  • Piazza della Cisterna - Piazza della Cisterna is a charming medieval square situated in the heart of San Gimignano. Surrounded by well-preserved medieval towers and historic buildings, the square takes its name from the ancient cistern located at its center. The triangular-shaped square is paved with medieval stones and exudes a timeless atmosphere. With its well-preserved medieval architecture and unique charm, Piazza della Cisterna stands as a captivating focal point within the UNESCO World Heritage site of San Gimignano.
  • Mura di San Gimignano - These well-preserved walls, dating back to the 13th century, served both defensive and symbolic purposes. The “Mura” offer a scenic stroll along their length, providing panoramic views of the charming town, its iconic towers, and the picturesque Tuscan countryside.
  • Monteriggioni - 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.

(*) November to March, the Tour does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier.

  • Chianti Road - 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”.
  • Siena - 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. 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,
  • Piazza Salimbeni - Our Siena Guided Visit starts from Piazza Salimbeni where Palazzo Salimbeni is located. The ancient Palace hosts the first and oldest Bank in the world.
  • Piazza del Campo - Piazza del Campo, of which the Palazzo Pubblico (Town Hall) is the focal point
  • Duomo di Siena - you will get to the spectacular Cathedral of the 12th century (inside visit if option selected), of which you can admire the magnificent architecture and the splendor of the polychrome marbles.

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

  • Biblioteca Piccolomini - Only if cathedral entrance option is selected - The Piccolomini Library, housed within the Duomo di Siena, is a Renaissance gem adorned with vibrant frescoes by Pinturicchio. Commissioned by Pope Pius III, these artworks depict scenes from his life, creating a cultural and artistic treasure within the Siena Cathedral.
  • Via Chiantigiana - Coming back to Florence you’ll drive through the Chiantigiana road, a scenic route that winds through the picturesque Chianti region. This iconic road takes travelers through rolling hills adorned with vineyards, olive groves, and charming villages. Along the way, you’ll encounter classic Tuscan landscapes, medieval castles, and renowned wineries producing the world-famous Chianti wine. The journey along Via Chiantigiana offers a delightful blend of cultural richness, culinary delights, and breathtaking views, making it a popular route for those seeking an authentic Tuscan experience.
What's Included
  • Siena Cathedral interior Guided Visit including entrance fee (if option selected)
  • Licensed Tour Leader with live commentary on board
  • Monolingual Visit in Siena (April to October)
  • 3 course set-menu typical Tuscan lunch in a Chianti Winery
  • Transport by G.T. air-conditioned coach
  • Local guide in Siena (if option selected)
  • Tasting of three different Chianti Wines, extra virgin olive oil & “vin santo”
What's Not Included
  • Our Shared Round Transport option does NOT include: Siena Guided Visit, Cathedral admission
  • From November to March, the itinerary does not include the stop at Monteriggioni
Additional Information

Discover the timeless allure of Tuscany on an immersive full-day journey! Step into the enchanting past of San Gimignano, often dubbed the “Manhattan of the Middle Ages” for its towering skyline. Traverse its cobblestone streets, steeped in history, and soak in the panoramic views of this captivating Tuscan hill village.

Next, delve into the cultural richness of Siena as your expert guide unveils its treasures during a comprehensive tour of the spellbinding old town. Immerse yourself in the traditions and heritage that make Siena an icon of Italy.

Explore the quaint Monteriggioni Hamlet (*). Then, prepare your senses for a typical Tuscan lunch, while savoring exquisite wines, each sip telling a tale of the region’s rich viticulture, a perfect finale to your day in Tuscany’s heart.

Please note that the order of the visits may change

(*) November to March, the Tour does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier

  • A dress code is required to enter places of worships and selected museums. No shorts or sleeveless tops are allowed. Knees and shoulders MUST be covered for both men and women. This dress code is strictly enforced and you will risk refused entry if you fail to comply with requirements.
  • For small groups, up to 8 pax, the Tour escort service could be replaced with an English speaking driver-guide service, while maintaining unchanged the entire program of the excursion.
  • Comfortable walking shoes are recommended.
  • From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
  • It is mandatory to arrive at the meeting point at the mentioned check in time. In case of delay it will not be possible to join the tour, nor to have a refund or reschedule the tour.
  • Please be advised that it is required to bring your original ID with you during the tour.
  • Clients with motor disabilities or wheelchair users are encouraged to notify the tour organizer in advance and seek medical advice to ensure suitability of services. Our tours and transportation are not suitable for people with motor disabilities or wheelchair users, so to prioritize the safety and well-being of all involved, the driver and tour manager retain the right to decline participation if they believe it may compromise safety. This decision rests solely with them, and no compensation will be provided in such cases. By accepting these terms, clients agree to respect decisions made by staff regarding participation.
Location
Piazzale Montelungo
Check in time: 07:45am - Montelungo Square, at the end of the ramp connecting with the train station. An assistant will be waiting for you wearing blue clothing with CAF Tour - Gray Line logos.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.4
(3300 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
E206losabrinaf
Jul 30, 2024
I had a fabulous time! - I had an amazing trip. My tour guide was Fabiana and my driver was Enrico. I loved the people we met and the places we saw. I had an overall wonderful day and I know my whole family did as well.
Review provided by Tripadvisor
Gosia
Jul 28, 2024
Perfect! - The tour was great. Beautiful Tuscany towns in one day. Federico was an amazing guide together with the driver Elis made the trip very enjoyable. Lovely winery experience, great food and wine. Thank you!
Review provided by Tripadvisor
Jiyongk437
Jul 28, 2024
wonderful place - The tour includes wonderful places (San gimignano, Monteriggioni, and Siena) San Gimignano was a great place that has beautiful architectures and delicious gelato.
Review provided by Tripadvisor
Meander61994096886
Jul 28, 2024
I recommend this tour - With thoughtful guide Federico and best driver Elis, it was a nice round trip to Tuscany cities. I like whole small cities. I hope the order of destination can be altered in Summer because I was exhausted in Siena since the weather was too hot even this city is the main spot.
Review provided by Tripadvisor
N7353ebcynthiap
Jul 28, 2024
5 star! - Our day tour was wonderful! Federico was a great guide, and we thoroughly enjoyed the entire experience. Can't forget to mention how safe and smooth the bus ride was thanks to our driver, Elis!
Review provided by Tripadvisor
Lori0402
Jul 28, 2024
Great tour! - The service and experience was excellent. Federico and Elis were great and very informative. We especially enjoyed the wine tour and all the great food and tasty wine.
Review provided by Tripadvisor
Gabord426
Jul 30, 2024
Great family day in Toscana - Great day for our family. The multiple stops made the experience more enjoyable. Love the medieval city of San Gimignano, the lunch with wine (Poggio ai Laghi) and the Cathedral of Siena (Duomo). I nearly forgot the gelateria Dondoli!!! Thank to Fabiana our guide and Enrico our bus driver.
Review provided by Tripadvisor
Margarita_p
Jul 28, 2024
Great tour but food not very good - Enjoyed going to all the sites, however would never book again in the summer. Too hot. Guide was awesome. Did not enjoy the lunch and wine tasting at Chianti. the food was very mediocre.
Review provided by Viator
Benjamings9649ve
Jul 28, 2024
Guide in tuscany - The weather was amazing and every spot we went to was amazing and good scenery. Good service from guide and bus driver. A little morr time at the wineyarf would be preferred.
Review provided by Tripadvisor
Matthew_f
Jul 30, 2024
Good Day with a Mediocre Winery Thrown In - This tour is a great way to see three medieval Tuscan cities in one day. The tour guides and driver were great! Our tour guide Vera gave great insight into each city and was very thorough when leaving to make sure we had everyone. However, the company can pick a better winery to send people to in Tuscany. The il Ciliegio winery was a bit of a let down. The food was ok and they kind of just threw three wines in front of you without much explanation of each one or direction on how to taste the wines. The atmosphere of the winery as a whole was just ok. I’ve been to other Tuscan wineries that give a five star experience with their wine tasting, food, and overall atmosphere. Il Ciliego was more of a two star experience. However, this tour was a good way to experience the cities in Tuscany in one day.
Review provided by Viator
Select Date and Tickets
up to 8 guests
1 Adult
September 2024
Sun
Mon
Tue
Wed
Thu
Fri
Sat
Today