Siena, San Gimignano and Chianti Wines Day Tour from Florence
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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
4.6/5
Based on 3,288 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Siena, San Gimignano and Chianti Wines Day Tour from Florence worth booking?
Siena, San Gimignano and Chianti Wines Day Tour from Florence is a 10.5-hour experience in Florence, Italy, from $33 per person. It scores 84 out of 100 on the Outty Ranking, which we label “Exceptional”, based on a 4.6/5 rating across 3,288 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 84 / 100
- Rating
- 4.6/5 (3,288)
- Duration
- 10.5 hours
- From
- $33 per person
A full day tour, taking in the key beauties of Central Tuscany including a delicious Chianti wine tasting. You'll roll through the sweeping countryside to arrive at the jewel of Siena, with its unique Square and Gothic T
What you get
About this experience
A full day tour, taking in the key beauties of Central Tuscany including a delicious Chianti wine tasting. You'll roll through the sweeping countryside to arrive at the jewel of Siena, with its unique Square and Gothic Town Hall. Then you'll take the road for San Gimignano, the Medieval New York, and Monteriggioni - a hilltop castle with breath taking views. But it's still not over! End your visit with a Chianti winery where you savor the best of Italian wines. This is a perfect day-out to relax and replenish your spirits.
What's included
Included
- Free time in San Gimignano and Monteriggioni Medieval towns
- Gran Turismo Luxury bus travel with WiFi on board
- Expert multilingual Tour Leader
- Visit to a charming Chianti wine estate with tastings of up to 2-3 Chianti wines and regional snacks
- Siena tour with professional guide with Headsets (not included in the "+ Free Time" option)
Not included
- Gratuities
- Hotel pickup and drop-off
- Siena Cathedral tickets (approx. 7€ pp)
- Lunch
What you'll see and do
There is no time to waste when exploring the stunning Tuscany hills! Meet your tour guide at Piazzale Montelungo Bus Terminal early in the morning. Piazzale Montelungo is located 5-10 minutes walking distance from the Santa Maria Novella train station. Hop on the comfortable coach bus, choose your seat, and relax before departing on your journey! The drive to Monteriggioni will take about one hour. During the journey, your guide will entertain you with plenty of interesting information about Tuscany and its sights on the way. Upon arrival, your expert guide will share some interesting information and fun stories about Monteriggioni! If you have any questions, your guide will be there to assist you.
45 minutes here
Monteriggioni
After about 40 minutes by bus, arrive in Monteriggioni, a charming medieval fortress set atop a hill. Enjoy 45 minutes of free time to stroll through the village squares and soak up its timeless atmosphere. Guests may also choose to walk along the fortress walls (optional, extra cost).
60 minutes here
Siena
Continue to Siena, one of Tuscany’s most beautiful historic cities. Guests who select the Classic Tour option will enjoy a 1-hour guided walking tour with a professional guide, focusing on the city’s main highlights (exterior visits only). Guests with the Semi-Independent option will have approximately 2.5 hours of free time to explore Siena at their own pace.
180 minutes here
Piazza del Campo
During the guided tour, admire Piazza del Campo from the outside, one of Europe’s most stunning medieval squares. Your guide will explain its unique shell shape and its role as the setting of the famous Palio horse race, as well as the exterior of the Palazzo Pubblico and the Torre del Mangia.
30 minutes here
Duomo di Siena
The final stop of the Siena visit is the Siena Cathedral, admired from the outside. Learn about this magnificent example of Italian Gothic architecture, renowned for its intricate marble façade.
30 minutes here · Admission not included
San Gimignano
After lunch, travel on to San Gimignano, the medieval town famous for its skyline of towers. Enjoy free time to wander through its cobblestone streets, browse local shops, or relax with a coffee in one of the charming squares.
60 minutes here
Collegiata di Santa Maria Assunta - Duomo di San Gimignano
During your free time, you may choose to visit the Collegiata, the town’s main church, known for its well-preserved frescoes and Romanesque architecture (entrance optional).
15 minutes here · Admission not included
During your free time in San Gimignano, you may choose to stop at the famous Gelateria Dondoli, an award-winning gelato shop located in the main square. This is a great opportunity to taste some of Italy’s most renowned artisanal gelato (not included in the tour price).
5 minutes here · Admission not included
In the evening, relax on the journey back to Florence, bringing an unforgettable day in Tuscany to a close.
60 minutes here
Where it starts and ends
Meeting point
Florence
TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!
Options you can book
Italian With Free Time
What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
French With Guided Siena
All inclusive tour in French: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
French With Free Time
What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
Audio Guided Tour Japanese
Historical explanations will be via audio guide (App) in Japanese. A Tour Leader will coordinate and provide lnfo in English.
Chinese Audio Guided Tour
Audio Guided Tour Chinese: Historical explanations will be via audio guide (App) in chinese. A Tour Leader will coordinate and provide lnfo in English.
Spanish With Free Time
What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
Spanish With Guided Siena
All inclusive tour in Spanish: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
Audio Guided Tour Korean
Historical explanations will be via audio guide (App) in Korean. A Tour Leader will coordinate and provide lnfo in English.
Portuguese With Free Time
What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
English With Guided Siena
All inclusive tour in English : Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
Italian With Guided Siena
All inclusive tour in Italian: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
English with Free Time
What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- ko, pt, cmn, ja, en, it, fr, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- Ciao Florence Tours Srl
Know before you go
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Infants are required to sit on an adult’s lap
- Specialized infant seats are available
- Not recommended for travelers with poor cardiovascular health
- Travelers should have at least a moderate level of physical fitness
- May be operated by a multi-lingual guide
- Please note that the given order of the visits may change
- Kindly note that the Semi independent option does not include the professional guide in Siena
- LOW SEASON (From November, 1st until March, 31st): English and Spanish languages are always guaranteed. In order to confirm the excursion in French, Italian or Portuguese a minimum of 4 pax is required
- HIGH SEASON (From April 1st until October 31st): this tour is always available in English and Spanish. Other languages are confirmed as follows: FRENCH: Tuesday - Friday, min 2 pax PORTUGUESE: Wednesday - min 2 pax ITALIAN: Saturday, Sunday - min 2 pax
Photos
What travelers are saying
Outty’s summary of the themes that recur across 3,290 traveler reviews. Written by us, not quoted from reviewers.
The guide
5 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
3 mentionsReviewers describe the commentary as informative rather than scripted.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Value for money
2 mentionsTravelers feel they got more than they paid for.
Organization
2 mentionsPickup, timing, and logistics are described as running smoothly.
Pace and timing
2 mentionsSeveral reviewers comment on how the schedule is paced.
Traveler reviews
3,290 verified traveler reviews for Siena, San Gimignano and Chianti Wines Day Tour from Florence. Ratings and reviews provided by Viator and Tripadvisor.
Super tour and tour guides!
Today has been super! The driver Mario drove us all over comfortably and safely! The bus was super. Lyon and Samuel were brilliant guides throughout! Dealing with English and Spanish speaking guests no problem. Their knowledge of all locations was excellent and delivery super. Laura was our tour guide for Siena. Whilst she was good it did feel a little rushed. The tour is so good and great value. Book it now, you will not regret it.
via Tripadvisor
Awesome experience
Great experience! We have used this your guides before and was a great experience as well. Samuel, Mario and Lyon were great!
via Tripadvisor
Great experience!
Thank you so much for the staff, specially Samuel for all of your attentions. He was very patient and polite. Great amount of time and activities.
via Tripadvisor
Great tour, great places
All the places where great and beautiful
via Tripadvisor
Tremendous trip
Big appreciate to Rio, Samuel and Mario.
via Tripadvisor
Good to know
- Duration
- 10.5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $33 to $75
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 1,151
- Verdict
- Exceptional
Why this scores 84
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Siena, San Gimignano and Chianti Wines Day Tour from Florence: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Siena, San Gimignano and Chianti Wines Day Tour from Florence cost?
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Prices start at $33 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 Siena, San Gimignano and Chianti Wines Day Tour from Florence take?
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Plan for about 10.5 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 Siena, San Gimignano and Chianti Wines Day Tour from Florence worth it?
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It holds an Outty Ranking of 84 out of 100, which we label "Exceptional". That score blends traveler sentiment (4.6/5 across 3,288 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 Siena, San Gimignano and Chianti Wines Day Tour from Florence?
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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 Siena, San Gimignano and Chianti Wines Day Tour from Florence suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 10.5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Siena, San Gimignano and Chianti Wines Day Tour from Florence?
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Around 1,151 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 10.5-hour experience runs outdoors or after sunset.
Where does Siena, San Gimignano and Chianti Wines Day Tour from Florence 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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