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

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Summary
Experience Details
What You’ll Experience
Where to Meet
Reviews
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Duration
11 hours
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Number of Guests
1 - 8 guests
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Language
English, Spanish
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Digital Ticket
Mobile or paper ticket accepted

Uncover Tuscany's charm with a day trip to San Gimignano, Siena, Monteriggioni, and Chianti. Enjoy guided tours, immerse in history, and indulge in a Tuscan lunch with exquisite wine tasting.

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For each guest that attends this experience, byFood will donate
10 meals

Experience Details

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     

What You Get

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
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

Good To Know

  • 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.
  • 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.
  • 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.
  • 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.
  • From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
  • Please be advised that it is required to bring your original ID with you during the tour.

What You’ll Experience

1

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.
2 hoursAdmission Ticket Free
2

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.
10 minutesAdmission Ticket Free

Mura di San Gimignano (Pass By)

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.
3

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.
40 minutesAdmission Ticket Free
4

Strada Statale 222 Chiantigiana

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".
1 hour 30 minutesAdmission Ticket Included
5

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,
2 hours 30 minutesAdmission Ticket Free
6

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.
15 minutesAdmission Ticket Free
7

Piazza del Campo

Piazza del Campo, of which the Palazzo Pubblico (Town Hall) is the focal point
15 minutesAdmission Ticket Free
8

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
15 minutesAdmission Ticket Included
9

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.
10 minutesAdmission Ticket Not Included

Via Chiantigiana (Pass By)

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.

Meeting & Pickup

Meeting Point

Piazzale Montelungo, Firenze Città Metropolitana di Firenze Toscana, Italy, IT

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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.
End Point

This experience ends at the meeting point.

Cancellation Policy

Cancel your booking at least 24 hours before the experience start time to receive a full refund minus a 3.2% transaction fee.

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What People Are Saying
Overall ratings and reviews
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(4090)
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Very informative guide...
July 11, 2025
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(Viator)

Very informative guide (Hilary) who took us through the beautiful Tuscan countryside & medieval villages

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A great way to visit the region in a day.
July 11, 2025
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(TripAdvisor)

Fabi our guide was great, took good care of us (driver also very good and the coach was very comfortable) she gave us just the right amount of information to enjoy our trip. We had a great day and...read more

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The Sienne and co tour.
July 08, 2025
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(Viator)

Punctual departure, Alessandra (our guide) and Ferdinando, our bus driver (I hope I got his name right) were excellent. Alessandra explained everything in English and Spanish. She was very attenti...read more

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Unforgettable tourist experience
July 07, 2025
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(TripAdvisor)

Excellent tour and guide team. I am very grateful to guide Marta for turning this tour so wanted by us into an unforgettable experience with her guidance and explanations in every place we visited....read more

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Great value for money. A...
July 06, 2025
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(Viator)

Great value for money. A wonderful way to see parts of northern Italy in a day. Martha was an amazing guide. Funny too and managed a large group with ease.

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from  $91.27 
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Please note that the time is in Central European Time.
Free cancellation (24 hours notice)
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Earliest available date: July 15, 2025
from  $91.27  per guest
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Please note that the time is in Central European Time.
Free cancellation (24 hours notice)
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For each guest that attends this experience, byFood will donate
10 meals
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