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
English 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
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
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
4,263 reviews
Total reviews and rating from Viator & Tripadvisor
Long day but worth it
Sarah P,
Sep 29, 2025
- Viator
4.00Other reviews are correct- this is not a guided tour. However, I liked how we are on our own in each city rather than having to keep up with a guide and large group. Hilary was very sweet and gave us information about each city before exiting the bus. The winery was just a tasting experience (4 wines) with lunch. I thought they gave us a lot of food: bruschetta, meats, cheese, a full portion of pasta with ragu, and biscotti. Personally I was full after it. The employees there were very energetic and fun. Be prepared for a lot of walking. Uneven streets and hills. This tour is not for those who have trouble with balance. It’s a long day.
A Tuscan Adventure
Lucy Q,
Sep 28, 2025
- Viator
4.00This tour is a great way to see unesco towns with lots of history and charm in one day. It also included a light lunch which was only 2 courses not 3 as described and wine tasting which you can buy, if you don’t drink wine you get water.The guides Frederico Lillie and Fabbie were friendly and helpful. Overall an enjoyable day. Read less
100% recommended
Karem B,
Sep 28, 2025
- Viator
5.00Hilaria was our guide, she did a wonderful job, she gave us a lot of information without being overwhelming. The visit to the winery and lunch was delightful. I 100% recommend this tour .
Views, wine and beauty!
Kimberly G,
Sep 25, 2025
- Viator
5.00Great experience with an opportunity to see a lot! My only recommendation would be that if you have the cathedral guided tour, have it start when you arrive in Sienna so you have a little bit more free time.
CAF tour was about as bad as it gets
Gary N,
Sep 24, 2025
- Viator
1.00We have been to Italy many times and have been on dozens of tours. This tour was - by far - the worst tour ever. There were 75-80 people on our tour. Who would ever sign up for a tour, anywhere, with that many people? We were loaded onto a double decker bus and the tour company paired our English speaking tour with a Spanish speaking tour. Every discussion/announcement was in 2 languages. Moving that many people from one location to the next was an effort and took away from the time that could have been spent in any of the location stops. One of the worst parts of the day was the lunch location and food/wine offered. The tour company booked a very commercial location and there were hundreds of people there (the buses just kept arriving). The "three course meal" consisted of stale bread with a small tasting of meats/cheeses, a very inferior pasta course with a meat ragu (you could honestly barely see or taste), and dessert was a plate of biscotti on the table (everyone was offered 1 biscotti as dessert). This was so disappointing and not an authentic experience. This tour company (CAF Tour and Travel) has moved away from providing a quality experience to tourists to just taking everyone's money. Avoid this at all costs.
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Operated by CAF Tour and Travel