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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch

4.5 Great 5156 reviews
|
11h
|
English, Spanish
Free cancellation Instant confirmation Live guide

Ratings & Reviews

4.5
5156 reviews
5
3556
4
1031
3
314
2
164
1
91
Ratings collected from Guidekin & Viator & Tripadvisor

Guidekin's take

Farm lunch and Monteriggioni in our Siena & San Gimignano Day Trips comparison.

Trade-off: Monteriggioni skipped November to March.

Last checked: September 18, 2026. Commissions never affect our verdicts.

Overview

Guidekin summary

A coach loop with free time in San Gimignano, a stop inside the walls of Monteriggioni, three wines and a three course farm lunch in Chianti, then a guided walk of Siena with a cathedral entry tier. Monteriggioni drops out from November to March; knees and shoulders must be covered for the churches. 4.51 from 5,156 reviews at €71 per person.

From the guide

Discover Tuscany in one day from Florence. Begin in the hilltop UNESCO town of San Gimignano with about 2 hours of free time to explore towers, lanes, and artisan shops. Continue to Monteriggioni (seasonal; see note), a perfectly preserved walled village, with time to wander inside the walls. Cross the rolling Chianti hills to a cozy winery for a tasting of three wines and a three-course farm-to-table lunch, ending with cantucci. In the afternoon, enjoy a guided walking tour of Siena: stroll Piazza del Campo and see the Palazzo Pubblico, then admire the Cathedral (interior visit if option selected). Finish with free time before returning to Florence.

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

Tour options

The operator sells this tour in 6 versions. Prices are the operator's current list for two travellers; the calendar shows the exact figure for your date and party.

SPA Semi-Independent & Lunch

from €71 / person
Guide: Spanish

Spanish with Lunch & Wine: Round trip with tour Leader on board and Lunch with Wine Pairing. Not included: Siena Guided Visit & Cathedral admission

ENG Semi-Independent & Lunch

from €71 / person
Guide: English

English with Lunch & Wine: Round trip with tour Leader on board and Lunch with Wine Pairing. Not included: Siena Guided Visit & Cathedral admission

SPA Guided Tour - no Cathedral

from €97 / person
Guide: English, Spanish

Spanish without Cathedral: Tour Leader on board, Lunch with Wine Pairing, Guided visit in Siena. Not included: Cathedral admission.

ENG Guided Tour - no Cathedral

from €97 / person
Guide: English

English without Cathedral: Tour Leader on board, Lunch with Wine Pairing, Guided visit in Siena. Not included: Cathedral admission.

ENG Guided Tour with Cathedral

from €109 / person
Guide: English

Full English Tour & Cathedral: Tour Leader on board, Lunch with Wine Pairing, Guided visit in Siena with Cathedral admission.

SPA Guided Tour with Cathedral

from €109 / person
Guide: Spanish

Full Spanish Tour & Cathedral: Tour Leader on board, Lunch with Wine Pairing, Guided visit in Siena with Cathedral admission.

Schedule & Availability

Runs daily
Departs: 08:00
Scheduled through October 2027

This tour runs daily, departing at 08:00. Scheduled through October 2027. These are the operator’s scheduled departures, not a live seat count: availability is confirmed at checkout. Schedule last checked September 18, 2026.

What's Included

Siena Cathedral and Libreria Piccolomini entrance with guided visit (if option selected)
Comfortable G.T. Coach transport from Florence in a modern, air-conditioned bus
Immersive journey led by a Licensed Multilingual Tour Leader (English & Spanish)
If option selected: from November to March the visit in Siena can be bilingual (English and Spanish)
If option selected: April to October, visit in Siena is monolingual. Language selected while booking
Dedicated Caf Tour & Travel Staff Assistance at the meeting point
Chianti Winery experience: Guided Cellar visit plus 3-course Tuscan lunch & 3 Chianti Wines Tasting
Guided tour in Siena with Earphones provided (if option selected)

What's Not Included

From November to March, the itinerary does not include the stop at Monteriggioni
Hotel pick up and drop off

Itinerary

San Gimignano Stop 1
Discover the UNESCO-listed “town of towers,” a perfectly preserved medieval hilltop gem with panoramic views, artisan boutiques, and photogenic alleys. Enjoy ample free time for your own exploring, from award-winning gelato to snapshots of the skyline—ideal on a day trip from Florence.
2h
Piazza Della Cisterna Stop 2
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.
Pass by
Mura di San Gimignano Stop 3
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.
Pass by
Monteriggioni Stop 4
Step inside a storybook fortress village encircled by intact walls and ramparts, beloved by filmmakers and history fans alike. Enjoy free time to browse tiny craft shops, stroll the piazza, and soak up authentic medieval Tuscany. (*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
40 min
Siena Stop 5
Join a guided walking tour (if option selected) through contrade banners, artisan storefronts, and grand palazzi that reveal Siena’s golden age. Afterward, enjoy free time to sip an espresso, browse boutiques, or continue exploring this Gothic masterpiece at your own pace.
2h 30m
Piazza del Campo Stop 6
is the main square of Siena, famous for its distinctive shell shape and elegant brick pavement. Surrounded by historic buildings, it is home to the Palazzo Pubblico and the Torre del Mangia. It is also the setting for the famous Palio di Siena, a historic horse race between the city’s districts.
15 min
Duomo di Siena Stop 7
Cathedral Entrance and inside guided visit only if option selected - officially known as the Cathedral of Santa Maria Assunta, is a stunning medieval cathedral in Siena. Renowned for its distinctive Gothic architecture, the cathedral showcases a magnificent facade adorned with intricate sculptures. Inside, visitors can marvel at remarkable works of art, including frescoes, mosaics, and statues by renowned artists like Donatello and Michelangelo. The cathedral's breathtaking interior also features a striking marble pavement and a magnificent Piccolomini Library.
30 min
Admission included
Biblioteca Piccolomini Stop 8
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.
15 min
Admission included

Departure & Return

Start point

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

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.

Additional Information

  • 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.
  • Vegetarian and gluten-intolerant options are available at the wineries; however, cross-contamination cannot be fully excluded.
  • 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.

1+ daysFull refund
0-1 daysNo refund

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