
Exclusive Tour from Florence: Siena, Chianti and San Gimignano
Pick your date
Highlighted days have spots open. Grey days are sold out or not running.
September 2026
Loading live availability
Who is going?
Adults
Age 13 and over
Children
Age 12 and under
Select a highlighted day to see live departure times and the exact price for your group.
Non-refundable booking. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 3 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Exclusive Tour from Florence: Siena, Chianti and San Gimignano worth booking?
Exclusive Tour from Florence: Siena, Chianti and San Gimignano is a 8-hour experience in Florence, Italy, from $912 per person. It scores 42 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 3 reviews. This booking is non-refundable, so pick your date carefully. Same-day spots are currently showing.
- Outty Ranking
- 42 / 100
- Rating
- 5/5 (3)
- Duration
- 8 hours
- From
- $912 per person
This tour is designed for those who want to immerse themselves in the history, culture and flavors of one of the most fascinating regions of Italy. Stroll through the cobbled streets of the historic center of the city of
What you get
About this experience
This tour is designed for those who want to immerse themselves in the history, culture and flavors of one of the most fascinating regions of Italy. Stroll through the cobbled streets of the historic center of the city of Siena, admire Piazza del Campo and be enchanted by the beauty of the Duomo of Siena. Every corner of this city tells a story, and you will have the opportunity to experience it firsthand. Chianti, the region renowned throughout the world for its vineyards and fine wines, the cellars, where you can taste some of the best wines of the area, accompanied by delicious typical products with breathtaking views of the Tuscan hills. Finally, the city of Towers, San Gimignano, known as the "Manhattan of the Middle Ages" for its imposing towers that stand out in the sky. This village, declared a World Heritage Site by UNESCO, will fascinate you with its unique atmosphere and its streets full of history. Live an unforgettable experience among the wonders of Tuscany!
What's included
Included
- Private transportation
- Bottled water
- On-board WiFi
- In-vehicle air conditioning
Not included
- Lunch
What you'll see and do
Siena
After an hour of driving we arrive in Siena, a city declared a UNESCO World Heritage Site. Siena is famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race held twice a year. Walking around the city you can enjoy the main attractions from the outside. Palazzo Pubblico with the Torre del Mangi, the famous shell-shaped Piazza del Campo, home of the Palio di Siena and then the Duomo di Siena the Gothic cathedral with its beautiful interiors, including the mosaic floor and the Piccolomini Library
180 minutes here
San Gimignano
Between Siena and San Gimignano in the picturesque Tuscan countryside we stop at a winery for tasting of excellent wines and lunch. After lunch we will reach San Gimignano, a UNESCO World Heritage Site, a small medieval town surrounded by walls. Known as the City of Beautiful Towers, San Gimignano is famous for its medieval architecture, unique in the preservation of about a dozen tower houses, with its position on top of the hill and the walls that surround it forming "an unforgettable skyline". Mandatory stop to taste the best artisanal ice cream winner of numerous international awards.
300 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers. Pickup begins about 5 minutes before departure.
Before you book
- Cancellation
- All sales are final. No refund is available for cancellations.
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 7 travelers per booking
- Operated by
- Nash-TuscanyDrive
Know before you go
- Infants and small children can ride in a pram or stroller
- Specialized infant seats are available
- Suitable for all physical fitness levels
- Wine tasting: Minimum drinking age is 18 (soft drinks instead of wine)
Photos






What travelers are saying
Outty’s summary of the themes that recur across 3 traveler reviews. Written by us, not quoted from reviewers.
Food and drink
3 mentionsThe tastings and food stops are a highlight for most reviewers.
The guide
2 mentionsTravelers single out the guide as the reason the experience works.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Knowledge and storytelling
1 mentionReviewers describe the commentary as informative rather than scripted.
Traveler reviews
3 verified traveler reviews for Exclusive Tour from Florence: Siena, Chianti and San Gimignano. Ratings and reviews provided by Viator and Tripadvisor.
Highly recommend beautiful Tuscany
Second time I have done this tour and it is still one of my favorites. Michaela was an execellent guide and took us to a great winery where we had the most delicious lunch and wines
Response from the operator: Dear Karen, Many thanks you so much for your review!! It was a pleasur to have you on board.
via Viator
Fabulous day in Tuscany!!!
If you are looking for a day trip to Tuscany out of Florence, stop scrolling!!! You can’t find a better tour than the day we shared with Nash. From the start, his communication was excellent and timely. And we made it a challenge! We kept changing the number in our group, and he never skipped a beat. Even hiring a second car to accommodate us. We started with a stop at a beautiful winery and gorgeous views. Next up was the gorgeous town of Siena. Nash gave us plenty of time, suggested places to see, and was very clear on our meeting place. We lucked into a parade in the streets. But the highlight of the day (and possibly our entire trip to Italy) was the stop for lunch at a Tuscan farmhouse/winery. A wonderful wine tasting with a great explanations of the process. And an absolutely delicious lunch homemade by a Nonna! Then on to San Gimignano, the town of towers. This beautiful place enthralled us all. We returned safely back to our hotel in Florence. You could not find a better guide than Nash! He took dozens of pictures of our group, had great information and was an absolute pleasure to deal with. I highly highly recommend him!! A+++
Response from the operator: Thank you so much for this incredible review! It was a pleasure coordinating everything for your group (even the last-minute switches!), and I truly enjoyed spending the day with you all. Wishing you many more adventures just as memorable—grazie mille for your kind words and high recommendation!
via Viator
Nash was great!
Nash was wonderful! He set up an amazing wine day in Siena and San Gimignano for us. The tasting at Torciano was fabulous! Nash had a lot of knowledge about the area and could answer any question we had. He stayed in great contact with me and even continued to make suggestions for us after the tour was over. His van comfortably accommodated the five of us as he drove through the Tuscany area and he stopped at great photo opportunities for us! Nash will set up an unforgettable wine tasting day for you!
via Tripadvisor
Good to know
- Duration
- 8 hours
- Free cancellation
- Non-refundable
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 1
- Verdict
- Worth a Look
Why this scores 42
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Exclusive Tour from Florence: Siena, Chianti and San Gimignano: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Exclusive Tour from Florence: Siena, Chianti and San Gimignano cost?
+
Prices start at $912 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 Exclusive Tour from Florence: Siena, Chianti and San Gimignano take?
+
Plan for about 8 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 Exclusive Tour from Florence: Siena, Chianti and San Gimignano worth it?
+
It holds an Outty Ranking of 42 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 3 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable food & drink in Florence, and how flexible the cancellation terms are.
Can I cancel or reschedule Exclusive Tour from Florence: Siena, Chianti and San Gimignano?
+
No. This experience is sold on a non-refundable basis, so only book a date you are confident about. Similar experiences in the city do offer free cancellation if flexibility matters more than price.
Is Exclusive Tour from Florence: Siena, Chianti and San Gimignano suitable for kids and families?
+
Yes, all ages are welcome. Families should still weigh the 8-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Exclusive Tour from Florence: Siena, Chianti and San Gimignano?
+
Around 1 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?
+
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 8-hour experience runs outdoors or after sunset.
Where does Exclusive Tour from Florence: Siena, Chianti and San Gimignano start and how do I get there?
+
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?
+
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?
+
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?
+
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?
+
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.
Ready to lock in your spot?
Pick a date, choose your group, and see the exact price for Exclusive Tour from Florence: Siena, Chianti and San Gimignano.
Pick your date




