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

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Overview

Available languages

English
Spanish

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

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 hours • Admission Not Applicable
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 minutes • Admission Not Applicable

Options

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

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

Spanish Tour with Cathedral

Lunch
Siena Cathedral Visit included: It includes: Transport, Tour Leader on board, Typical Lunch, Siena Guided Visit and 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

English Tour with Cathedral

Lunch
Siena Cathedral Visit included: It includes: Transport, Tour Leader on board, Typical Lunch, Siena Guided Visit and Cathedral admission

Reviews

4.44

4,168 reviews

Total reviews and rating from Viator & Tripadvisor

2689
939
293
161
86
  • Tuscan tour

    Mike M,

    Sep 4, 2025

    - Viator

    4.00

    We had a beautiful day on an 11-hour tour around Tuscany to the 4 main towns. San Gimignano was our favourite. Grapes and Olive trees galore, so pretty. We had a Tuscan lunch at a winery near Sienna. The tour guiide, Fabi and driver Adriano were a good lively team.

  • Great tour!

    Stephanie P,

    Sep 1, 2025

    - Viator

    5.00

    Very good tour, Hillary was a fantastic guide leading us through Tuscany’s gems. The lunch was fantastic, provided at a small family vineyard. Definitely recommend if you’d like to visit more of Tuscany from Florence!

  • It was a great full day tour!

    Kellsi R,

    Aug 29, 2025

    - Viator

    5.00

    We had bus driver Ellis and tour guide Ricardo. And they did a great job! We only did the wine tasting, not the Siena tour and cathedral. It was easy to find the meeting point. We stopped first in San Gimignano which was quiet and cute. Most things were still opening up. We got to see a great view from the top of one of the towers. The we headed to Monteriggioni, a Medieval castle. The tour of the wall was closed for construction. But we found a cute little wine shop, Poggio ai Laghi, where we did a short tasting! Then we headed to lunch at the vineyard, ristorante il Celiegio. We couldn’t see much of the grapes vineyard. But they had the olive trees looking out from the restaurant. Then we headed to Siena where we had about 2.5 hours of free time. We saw the Duomo and the Piazza del Campo. Overall it was a long but great day!

  • Guide Fabi was great,...

    David G,

    Aug 26, 2025

    - Viator

    5.00

    Guide Fabi was great, well organised, clear with times etc. Good sense of humour! A really good day with lunch and wine tasting. Great driver Silvio!

  • Plenty of time

    Scott B,

    Aug 20, 2025

    - Viator

    4.00

    The best part of this tour was that it was constructed to allow plenty of time at each stop -- we never felt rushed. The lunch/wine tasting was particularly well-done. There were a couple of stumbles, though: Our guide didn't know that a couple of attractions (like walking on the walls at Monteriggioni) were unavailable; and he did not offer tips on where to find water (this on a 103-degree day) or where to find public restrooms.

From €79.00

4.44
4,168 reviews
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