San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting
Overview
Available languages
11 hours
Mobile ticket
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
Additional Info
Infants and small children can ride in a pram or stroller
Public transportation options are available nearby
Specialized infant seats are available
Travelers should have at least a moderate level of physical fitness
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 or no show 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.
Once the audio guides are handed over before the guided tour, they become the full responsibility of the customer. In case of loss, a fee of €80 will be charged.
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.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What‘s Included
Siena Cathedral interior Guided Visit including entrance fee (if option selected)
Licensed Tour Leader with live commentary on board
from April to October - monolingual Visit in Siena
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”
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
What To Expect
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.
Options
Spanish-Shared Round Transport
Lunch
Shared round Trasport & Lunch: It includes: Transport, Tour Leader on board, Typical Lunch.
Not included: Siena Guided Visit and Cathedral admission
Spanish Tour with Cathedral
Lunch
Siena Cathedral Visit included: It includes: Transport, Tour Leader on board, Typical Lunch, Siena Guided Visit and Cathedral admission
English-Shared Round Transport
Lunch
Shared Round Transport & Lunch: It includes: Transport, Tour Leader on board, Typical Lunch.
Not included: Siena Guided Visit and Cathedral admission
Tour in English
Lunch
Shared Day Trip from Florence: It includes: Siena Guided Visit, Lunch and wine tasting, Transport, Tour Leader on board.
Not included: Cathedral admission
English Tour with Cathedral
Lunch
Siena Cathedral Visit included: It includes: Transport, Tour Leader on board, Typical Lunch, Siena Guided Visit and Cathedral admission
Tour in Spanish
Lunch
Shared Day Trip from Florence: It includes: Siena Guided Visit, Lunch and wine tasting, Transport, Tour Leader on board.
Not included: Cathedral admission
Reviews
4,348 reviews
Total reviews and rating from Viator & Tripadvisor
Too long too many...
Jackie C,
Oct 13, 2025
- Viator
3.00Too long too many directions. Too long in Siena. Restaurant was below average Felt like cattle being herded in
Absolutely recommend, do this tour to have in an insight into Tuscany Villages
Rachel C,
Oct 12, 2025
- Viator
5.00This was a great day tour, ie 11 hours duration and a great way to see the Tuscany villages of San Gimignano, Montereggiano, lunch at a Chianti winery and then onto Siena before travelling back on the coach to Florence. Martha, the main tour leader was excellent in explaining the details for the day, backed up by Stella and coach driver Genero who was a safe and good driver of the double decker bus. The tour is on a double decker bus ie 87 people onboard which I was totally put off by when arriving at the bus stop to check in for the tour. But once on board, and Martha explained the tour details, I was relieved. This tour is a great way to get yourself to Tuscany villages and around the Tuscany regions with spare time to explore yourself in each of the 3 towns/villages visited. The coach takes you to each town, then you have free time to explore yourself without being stuck with a large group of 87 people in our case. Each of the 3 towns/villages visited were truly beautiful and a great look at what Tuscany looks like in a day. Lunch at the Chianti winery was okay, not wonderful but what you would expect when a big winery is catering to multiple bus tours arriving from their Tuscan tour. We got to taste 4 Chianti wines which was great. Pasta of course for lunch but they catered for vegetarian. The tour departs at 8am and we returned by 7.30pm so a long day, but it didnt feel like this. Really enjoyable day and so pleased we did this tour. Would I recommend this tour, absolutely yes. Great value for money, and so much easier than trying to do this yourself ie taking trains and buses which would have been far more stressful. Seeing the Tuscany area is just so beautiful and please take the time out of visting the city of Florence and escape to a quieter, slower pace with this tour. Breathtaking scenery.
Trip To Siena
CAITLIN N,
Oct 12, 2025
- Viator
5.00Very thorough tour with three stops plus wine tasting and lunch. Everything was arranged for you when you book, and the guides are very thorough (we had Marta, Stella, and Gennaro as our driver) and tell you about the history of the towns and the region. (You will do a lot of walking on this tour.) I recommend for travelers who want to sit back and enjoy the region and let others do the day planning!
Perfect day in Toscana
Rowena M,
Oct 12, 2025
- Viator
5.00Beautiful lunch and towns visited, luxury coach and quality guide Constantino and Alessia / Alexa and driver Claudio was fab
A wonderful day in Tuscany
Clare B,
Oct 4, 2025
- Viator
5.00Lovely informative day to see a slice of Tuscany. Our guides were great and the bus very comfortable. Met some lovely people also. Would recommend this tour.
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Operated by CAF Tour and Travel