San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting | 11 hours

3648 Reviews | Florence
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From $75.36 per person   $83.74 Save $8.38 Lowest Price Guarantee
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Inclusions / Exclusions

  • Mobile ticket
  • Offered in: English, Spanish
  • 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 & ā€œvin santoā€
  • 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

Overview

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 regionā€™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 minutesĀ earlierĀ  Ā  Ā 

Meeting points

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 activity ends back at the meeting point.

Itinerary

  • San Gimignano

    Your memorable journey starts with the charming San Gimignano,Ā 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 ofĀ free time for a fascinating discovery.

    2 hours

  • 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 minutes

  • 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.

  • 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 minutes

  • SS 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 ā€œzero food milesā€ products which endsĀ with "cantucci e vin santo".

    1 hour 30 minutes

  • 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 minutes

  • 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 minutes

  • Piazza del Campo

    Piazza del Campo, of which the Palazzo Pubblico (Town Hall) is the focal point

    15 minutes

  • 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.Ā  Please note that the order of the visits may change

    15 minutes

  • 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 minutes

  • N/A (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.

Sample Menu

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-guideĀ 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.
  • 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.

Free Cancellation

February 05100% refund
February 06No refund

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experienceā€™s start time.
  • If you cancel less than 24 hours before the experienceā€™s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experienceā€™s start time will not be accepted.
  • Cut-off times are based on the experienceā€™s local time.
  • This experience requires good weather. If itā€™s canceled due to poor weather, youā€™ll be offered a different date or a full refund.
Reviews

4.4

3648 reviews

Total review count and overall rating based on Viator and Tripadvisor reviews
  • 5 stars
    2248
  • 4 stars
    888
  • 3 stars
    277
  • 2 stars
    154
  • 1 star
    81

Reviews by TravelOne travelers

Showing 1-5 of 2248 reviews with 5 stars

An Amazing Tour with a Few Bumps Along the Way

Published on Jan, 2025

Fabiana, our tour guide, was absolutely fantastic. Her extensive knowledge of the history and her detailed explanations made the experience truly memorable. Everything about the tour was lovely, but be preparedā€”it is a long day, lasting 11 hours. We found ourselves quite exhausted during the last three hours. One issue we encountered was the driverā€™s reckless driving. He frequently sped up over bumps in the road, causing discomfort. In fact, my partner hit his head while seated normally on the bus. If you get car sickness (as I am), I strongly recommend sitting toward the front of the bus to minimise the impact of the rough ride.

Fantastic experience in Tuscany

Published on Jan, 2025

We enjoyed all of it. The landscape, the food, the wine, the time for each activity, the guide Fabiana, who was very nice and capable, explaining every single detail with accuracy.

Great way to see a lot when you donā€™t have a lot of time.

Published on Jan, 2025

We really enjoyed the tour. As we were traveling in winter we ended up in a van instead of the bus which was great and our driver Danielle was amazing! The lunch was tasty but a bit long and focused on selling. Other than that we loved all of it. It was great seeing these sites less crowded.

Tuscany in one day!!

Published on Jan, 2025

It was a lovely day! Lots of free time but also a great schedule. Our guide and driver were wonderful! Aaron and Danielle! The food at lunch was lovely! I specially loved the camaraderie that Aaron promoted within the group! Highly recommended

Fantastic Tour!

Published on Jan, 2025

The tour was amazing! We had great recommendations from Frederico, our tour guide, and our driver Francesco was great as well. Overall, great experience and would highly recommend to others!

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