
Private Siena to Florence Chianti and San Gimignano Transfer Tour
Traveler rating
5.0/5
Based on 9 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Siena to Florence Chianti and San Gimignano Transfer Tour worth booking?
Private Siena to Florence Chianti and San Gimignano Transfer Tour is a 7-hour experience in Siena, Italy, from $903 per person. It scores 58 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 9 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 58 / 100
- Rating
- 5/5 (9)
- Duration
- 7 hours
- From
- $903 per person
Travel between destinations and visit sights along the way. Stop to visit the medieval fortress of Monteriggioni before spending leisure time in the hill-town of San Gimignano browsing the many stores or savouring the rich cuisine in one of its many restaurants (not included). In the afternoon visit the Chianti town of Greve in Chianti and the picturesque hamlet of Montefioralle before having your Private driver drop you off at your Florence destination.
What you get
About this experience
Travel between destinations and visit sights along the way. Stop to visit the medieval fortress of Monteriggioni before spending leisure time in the hill-town of San Gimignano browsing the many stores or savouring the rich cuisine in one of its many restaurants (not included). In the afternoon visit the Chianti town of Greve in Chianti and the picturesque hamlet of Montefioralle before having your Private driver drop you off at your Florence destination.
What's included
Included
- Florence Hotel drop-off
- Siena Hotel pickup
- Private Transportation in air-conditioned minivan
- Driver/guide
- Live commentary on board
Not included
- Lunch
- Gratuities
What you'll see and do
Tuscany
Have your Driver guide come and pick you up from your accommodation at 9:30am for the start of your transfer tour. As a first stop, visit the imposing fortress of Monteriggioni, a medieval village with complete ring of walls, built by the Sienese in the 13th century as a bastion of defense in their wars against Florence. It withstood all attacks from both the Florentines and the forces of the Bishop of Volterra until its keys were finally handed by the town’s captain over to the Medicean forces in an act of reconciliation.
Pass by without stopping
Tuscany
Continue to San Gimignano in the morning, this UNESCO protected hill-town is a testimony of Tuscan medieval architecture, with its austere towers that defiantly survived the centuries and the imposing rings of walls. This bustling gem is set among idyllic vine covered hills and is still flourishing with artisanal boutiques of the local trades and stores selling the towns ‘red gold’, the saffron spice. After lunch continue into the Chianti Classico on panorimic Chianti roads and arrive to the town of Greve in Chianti, famous for its oval square filled with artisan's shops and wine stores and for being the home town of the famous sailor Verrazzano. Here you have free time to sample wines and visit the stores. before continuing to Florence we stop one last time to visit a quaint and picturesque hamlet where we enjoy a walk along the cobbled streets and take in the breathtaking landscapes. Finally continue to your Florence destination after about 7 hours of tour.
Pass by without stopping
Where it starts and ends
Meeting point
Siena
Your Accommodation in Siena
Hotel pickup
Pickup is available for selected locations.
Ends at
Your Florence Accommodation
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- de, en, it, fr, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 6 travelers per booking
- Operated by
- Tuscan Escapes by Papilio SRL
Know before you go
- Specialized infant seats are available
- Infants and small children can ride in a pram or stroller
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
Photos






What travelers are saying
Outty’s summary of the themes that recur across 9 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
7 mentionsReviewers describe the commentary as informative rather than scripted.
Food and drink
3 mentionsThe tastings and food stops are a highlight for most reviewers.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
9 verified traveler reviews for Private Siena to Florence Chianti and San Gimignano Transfer Tour. Ratings and reviews provided by Viator and Tripadvisor.
Great ride and sightseeing!
It was a fabulous ride through villages and into Siena from Florence. Giovanni was extremely knowledgeable and friendly. We were thrilled to be able to take this tour with him.
via Tripadvisor
Wonderful!
This was our third and final tour with Tuscan Escapes. Our transfer tour was exceptional! Mattia made the tour fun, educational and tailored to what we were interested in. Would highly recommend Tuscan Escapes for their tours. Their staff is out of this world!
via Tripadvisor
Wonderful day trip with gorgeous views.
The views were spectacular. Our driver was so great! She was really knowledgeable, easy to understand, extremely personable. Highly recoiled this tour. And the lunch at the winery was delicious as were the wines.
via Tripadvisor
Great way to see Italy!
My boyfriend can be a nervous traveler, so I opted for private drivers from city to city, versus the train. This also allowed us to make stops along the way. This one in particular was excellent. The two stops were well worth seeing, and our driver dropped us off as close to the entrances as you can get, and was ready to pick us up once we were done. Very friendly driver.
via Viator
Day trip from Florence to Siena
Guiallaume picked us up in Florence for a San Gianmano to Siena tour. It was fantastic but the highlight was our guide. His energy and enthusiasm combined with his knowledge was fantastic. I’d do every tour offered if he was our guide again. Highlights were the lunch on the farm, and the flexibility offered as we had to be back to Florence earlier than planned. Five stars. Great experience for my wife and me and two teenage boys.
via Tripadvisor
Good to know
- Duration
- 7 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- Available for selected locations
- Booked in 30 days
- 3
- Verdict
- Worth a Look
Who runs this experience
Operated by Tuscan Escapes by Papilio SRL, who run 14 experiences we rank across 1 city, with an average Outty Ranking of 72.9 and 2 in the 90+ Club.
See everything Tuscan Escapes by Papilio SRL runsWhy this scores 58
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Siena to Florence Chianti and San Gimignano Transfer Tour: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Siena.
How much does Private Siena to Florence Chianti and San Gimignano Transfer Tour cost?
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Prices start at $903 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Siena usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Private Siena to Florence Chianti and San Gimignano Transfer Tour take?
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Plan for about 7 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 Siena is not rushed.
Is Private Siena to Florence Chianti and San Gimignano Transfer Tour worth it?
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It holds an Outty Ranking of 58 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 9 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Siena, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Siena to Florence Chianti and San Gimignano Transfer Tour?
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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 Private Siena to Florence Chianti and San Gimignano Transfer Tour suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 7-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Siena to Florence Chianti and San Gimignano Transfer Tour?
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Around 3 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 Siena 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 Siena and add a light layer if any part of the 7-hour experience runs outdoors or after sunset.
Where does Private Siena to Florence Chianti and San Gimignano Transfer Tour 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 Siena 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 Siena?
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On Outty we rank every Siena experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena, Siena: A Wine Tour and Tasting Experience, Small-Group Montepulciano and Pienza Day Trip from Siena. 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 Siena?
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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 Siena?
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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.
What is included in Private Siena to Florence Chianti and San Gimignano Transfer Tour?
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Included: Florence Hotel drop-off; Siena Hotel pickup; Private Transportation in air-conditioned minivan; Driver/guide; and Live commentary on board. Not included: Lunch; and Gratuities. Always check the voucher for the final list before you travel.
Does Private Siena to Florence Chianti and San Gimignano Transfer Tour include hotel pickup?
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Yes, pickup is offered, or you can meet at the start point instead from 7 listed pickup locations in and around Siena. You can also enter a custom pickup address when booking.
What languages is Private Siena to Florence Chianti and San Gimignano Transfer Tour offered in?
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It is offered in German, English, Italian, French and Spanish. Pick your language when choosing a date and time, as not every departure runs in every language.
Will I get instant confirmation and a mobile ticket for Private Siena to Florence Chianti and San Gimignano Transfer Tour?
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Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.
Is Private Siena to Florence Chianti and San Gimignano Transfer Tour wheelchair or stroller accessible?
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The operator notes: Specialized infant seats are available; and Infants and small children can ride in a pram or stroller. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to Private Siena to Florence Chianti and San Gimignano Transfer Tour if the weather is bad?
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It generally runs rain or shine, so dress for the forecast in Siena. Standard cancellation terms apply: free cancellation up to 24 hours before the start.
What do travelers say about Private Siena to Florence Chianti and San Gimignano Transfer Tour?
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Across 9 reviews averaging 5.0 out of 5, recurring themes include the guide, knowledge and storytelling, food and drink. Travelers single out the guide as the reason the experience works.
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