San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch
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September 2026
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Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.5/5
Based on 5,021 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch worth booking?
San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch is a 11-hour experience in Florence, Italy, from $40 per person. It scores 83 out of 100 on the Outty Ranking, which we label “Exceptional”, based on a 4.5/5 rating across 5,021 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 83 / 100
- Rating
- 4.5/5 (5,021)
- Duration
- 11 hours
- From
- $40 per person
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
What you get
- 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
About this experience
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
What's included
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)
Not included
- From November to March, the itinerary does not include the stop at Monteriggioni
- Hotel pick up and drop off
What you'll see and do
San Gimignano
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.
120 minutes here
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.
Pass by without stopping
Mura di San Gimignano
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 without stopping
Monteriggioni
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 minutes here
Siena
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.
150 minutes here
Piazza del Campo
Piazza del Campo 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 minutes here
Duomo di Siena
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 minutes here · Admission included
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.
15 minutes here · Admission included
Where it starts and ends
Meeting point
Florence
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.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
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.
Options you can book
SPA Semi-Independent & Lunch
Spanish with Lunch & Wine: Round trip with tour Leader on board and Lunch with Wine Pairing. Not included: Siena Guided Visit & Cathedral admission
ENG Guided Tour with Cathedral
Full English Tour & Cathedral: Tour Leader on board, Lunch with Wine Pairing, Guided visit in Siena with Cathedral admission.
ENG Guided Tour - no Cathedral
English without Cathedral: Tour Leader on board, Lunch with Wine Pairing, Guided visit in Siena. Not included: Cathedral admission.
ENG Semi-Independent & Lunch
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 with Cathedral
Full Spanish Tour & Cathedral: Tour Leader on board, Lunch with Wine Pairing, Guided visit in Siena with Cathedral admission.
SPA Guided Tour - no Cathedral
Spanish without Cathedral: Tour Leader on board, Lunch with Wine Pairing, Guided visit in Siena. Not included: Cathedral admission.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 8 travelers per booking
- Operated by
- CAF Tour and Travel - Gray Line Florence
Know before you go
- 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.
Photos
What travelers are saying
Outty’s summary of the themes that recur across 5,029 traveler reviews. Written by us, not quoted from reviewers.
The guide
7 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
5 mentionsReviewers describe the commentary as informative rather than scripted.
Food and drink
5 mentionsThe tastings and food stops are a highlight for most reviewers.
Traveler reviews
5,029 verified traveler reviews for San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch. Ratings and reviews provided by Viator and Tripadvisor.
Wine and sun in Tuscany
A delightful tour of the country side.
via Tripadvisor
Amazing!!!
Our guide Marta was fabulous! Ferdinando drove us around safely. Our under 15 year old children also enjoyed the experience with two highlights- the Siena cathedral and the food & wine tasting at one of the winery. The experience of seeing the fresh organic red Tuscan grapes was 5-star!
Response from the operator: Good morning from Caf Tour & Travel, Dear Customer, Thank you for sharing such a wonderful review! We’re delighted that you and your family enjoyed your day in Tuscany with Marta and Ferdinand. It’s lovely to hear that the Siena Cathedral and the food and wine tasting were highlights, and that your children enjoyed the experience too. We hope you’ll return one day to discover even more of the Tuscan countryside with us! Warm greetings from Tuscany, Caf Tour & Travel
via Tripadvisor
Brilliant
Wine tasting experience was amazing as well as the guide, plenty of stop offs and places seen. Only issue I experienced was not being able to understand the walking guide during the siena walk.
Response from the operator: Good morning from Caf Tour & Travel, Dear Customer, Thank you for your lovely review! We’re happy to hear that you enjoyed the wine tasting, the itinerary and the many beautiful places visited throughout the day. We’re sorry that you found the Siena walking tour difficult to follow and truly appreciate you sharing your feedback with us. We hope you still took home many wonderful memories of Tuscany and that we’ll have the pleasure of welcoming you again! Warm greetings from Tuscany, Caf Tour & Travel
via Tripadvisor
Wonderful Tuscan adventure
Had a wonderful Tuscan adventure, with lots of laughs, beautiful sights and (of course!) great wines. A special shout out to Ferdinand, our driver, and Marta, our very gifted and knowledgeable guide. Thank you!
Response from the operator: Good morning from Caf Tour & Travel, Dear Customer, Thank you so much for your wonderful review! We’re delighted that you had such a memorable Tuscan adventure filled with beautiful sights, great wines and plenty of fun. We’re especially happy to hear your kind words about Marta and Ferdinand, and we’ll be sure to share them with our team. We hope to welcome you back to Tuscany for another unforgettable day! Warm greetings from Tuscany, Caf Tour & Travel
via Tripadvisor
Highly recommend
Great tour, really informative, particularly impressive as Marta did it in both English and Spanish!
Response from the operator: Good morning from Caf Tour & Travel, Dear Customer, Thank you so much for your wonderful review! We’re delighted that you enjoyed the tour and found it so informative. We’re especially happy to hear that Marta’s ability to guide the group in both English and Spanish made the experience even more enjoyable. We hope to welcome you back soon to discover more of the beauty, history and flavors of Tuscany! Warm greetings from Tuscany, Caf Tour & Travel
via Tripadvisor
Good to know
- Duration
- 11 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $40 to $109
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 1,757
- Verdict
- Exceptional
Why this scores 83
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch cost?
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Prices start at $40 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Florence usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch take?
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Plan for about 11 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Florence is not rushed.
Is San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch worth it?
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It holds an Outty Ranking of 83 out of 100, which we label "Exceptional". That score blends traveler sentiment (4.5/5 across 5,021 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in Florence, and how flexible the cancellation terms are.
Can I cancel or reschedule San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 11-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch?
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Around 1,757 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Florence can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Florence and add a light layer if any part of the 11-hour experience runs outdoors or after sunset.
Where does San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Florence within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Florence?
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On Outty we rank every Florence experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Best tour in Florence: Renaissance & Medici Tales - guided by a STORYTELLER, Florence Pizza or Pasta Class & Gelato Making at a Tuscan Farm, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Florence?
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Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Florence?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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