
Private Siena to Florence Chianti and San Gimignano Transfer Tour
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September 2026
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Who is going?
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
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 $790 per person. It scores 59 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
- 59 / 100
- Rating
- 5/5 (9)
- Duration
- 7 hours
- From
- $790 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 ri
What you get
- Florence Hotel drop-off
- Siena Hotel pickup
- Private Transportation in air-conditioned minivan
- Driver/guide
- Live commentary on board
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






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
Why this scores 59
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 $790 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 59 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, Skip the Line: Siena Duomo and City Walking Tour, Siena: A Wine Tour and Tasting Experience. 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.
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