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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

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

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

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

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

Reviews

4.43

4,120 reviews

Total reviews and rating from Viator & Tripadvisor

2650
931
292
161
86
  • Exceptional!! Highly recommended

    Osvaldo L,

    Aug 3, 2025

    - Viator

    5.00

    Superb experience and guides! Lots of free time, no tourist traps, great wine tasting, good lunch, and exceptional guided tours, especially with Sandro!’

  • San Gimignano & Monteriggioni Wine & Lunch

    Elzette V,

    Jul 30, 2025

    - Viator

    5.00

    San Gimignano & Monteriggioni are beautiful ..worth the stop at the latter! I love Chianti & the Winery was great!♥️ Would have wanted more of the wine yards ..but then the half day Trip to San Gimignano with Picnic & Wine Tasting will be best! Our guide, Aaron is excellent ..multilingual, helpful & full of enthusiasm😎 As for Siena, you don’t need a guide & you can visit other more known Cathedrals ..

  • Well organised day....

    Tracey F,

    Jul 22, 2025

    - Viator

    5.00

    Well organised day. Beautiful cities and fabulous countryside . Ricardo our guide was very knowledgeable and very efficient . Wine tasting and lunch were most enjoyable with opportunity to chat to fellow holiday makers on this trip . A great day out .

  • Great tour

    Mariana B,

    Jul 20, 2025

    - Viator

    5.00

    We had a fantastic experience on this tour! The guide was excellent. He was professional, knowledgeable, and inclusive, making sure everyone felt welcome and engaged throughout the day. He also shared some great local tips that added extra value to our visit. The towns we explored were full of charm and character, each offering something unique and memorable. The bus was comfortable and the air conditioning was ideal, which made the journey smooth and enjoyable. Overall, it was a well-organised and enriching tour that we would absolutely recommend to anyone looking to explore Tuscany.

  • Shane train

    Jessica S,

    Jul 16, 2025

    - Viator

    5.00

    Lots of wine drinking makes this a fun trip! Aaron and Antonio did a fantastic job leading the trip and driving.

From EUR 79

4.43
4,120 reviews
Check availability

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