
Private daytrip to Siena & Chianti wine country, with wine tasting from Florence
Traveler rating
5.0/5
Based on 66 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private daytrip to Siena & Chianti wine country, with wine tasting from Florence worth booking?
Private daytrip to Siena & Chianti wine country, with wine tasting from Florence is a 8-hour experience in Florence, Italy, from €163 per person. It scores 80 out of 100 on the Outty Ranking, which we label “Exceptional”, based on a 5/5 rating across 66 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 80 / 100
- Rating
- 5/5 (66)
- Duration
- 8 hours
- From
- €163 per person
Private is just for you and your party, so the top in terms of flexibility, comfort, and privacy. Your knowledgeable English speaking driver, will discuss with you all the different options of the chosen itinerary, so you will be able to customize your day, to perfectly suit your needs and focus just on the attractions/activities you are interested in. Start your day with a relaxing visit of Greve in Chianti to learn about the country lifestyle, admire the beauties of the Chianti wine road and see postcard views, discover the secrets of the Chianti red wine, taste genuine products, and conclude your experience with a visit of Siena, Tuscany's second most important art city.
What you get
About this experience
Private is just for you and your party, so the top in terms of flexibility, comfort, and privacy. Your knowledgeable English speaking driver, will discuss with you all the different options of the chosen itinerary, so you will be able to customize your day, to perfectly suit your needs and focus just on the attractions/activities you are interested in. Start your day with a relaxing visit of Greve in Chianti to learn about the country lifestyle, admire the beauties of the Chianti wine road and see postcard views, discover the secrets of the Chianti red wine, taste genuine products, and conclude your experience with a visit of Siena, Tuscany's second most important art city.
What's included
Included
- Private transportation
- Other
- Initial briefing with the driver with explanation of the options, to let you build your perfect day.
- Private English-speaking driver, with fully equipped, Mercedes vehicle
- In-vehicle air conditioning
- Guided visit of 1 Tuscan winery followed by wine/olive oil tasting
Not included
- Guided tour of Siena and entrace fees in Siena (if applicable)
- Lunch
What you'll see and do
Greve in Chianti
After having met your driver at your accommodation in Florence, during the 45 minutes drive to reach Greve in Chianti, (the most famous village of the Chianti Classico countryside), he will explain all the details of your day, to be sure the schedule fits your needs. Once in Greve in Chianti, the birthplace of the famous Tuscan explorer Giovanni da Verrazzano, the Tuscan who discovered the New York Harbor, admire the Piazza Matteotti, a gently sloping square which is the hub of life in Greve; visit the many local shops and wine stores, including the famous butcher shop Falorni, or the Enoteca Le Cantine (one of the biggest wine shop in Tuscany)
45 minutes here
Strada Statale 222 Chiantigiana
After the visit of Greve in Chianti depart for a 30 minutes drive through one of the most beautiful wine road in Italy, full of rolling hills, huge vineyards and olive trees, typical of the Chianti Classico area.
Pass by without stopping
Panzano in Chianti
On the way to the winery admire the charming Tuscan hilltop village of Panzano in Chianti, located exactly halfway between Florence and Siena, with the curch of Santa Maria Assunta and the imposing Tower of the Castle.
Pass by without stopping
Fattoria di Montecchio
Your experience at the winery will start with an introduction about the history of the estate, followed by the visit of the old wine cellars with the explanations about the wine making process, and all the secrets to produce the Chianti red wine and the Tuscan olive oil, famous all over the world. After the visit, take a seat and taste different wines (Chianti Classico, Riserva, Super Tuscans, etc.) and the olive oil, one of the most important ingredients of the italian cooking. In case Fattoria Montecchio is not available, you will visit another wine estate in the same area.
60 minutes here · Admission included
San Donato in Poggio
For food lovers, just 5 minutes away from the wineries, there is a family owned restaurant called La Locanda di Pietracupa, where you can taste one of the best and most genuine food of Tuscany, paired with a great selection of local wines. This is just an option in case you like to have a lunch at a restaurant; obviously being lunch at your own expenses, you are free to decide where to go, or skip the restaurant and eat something faster in Siena.
Pass by without stopping
Siena
In Siena your driver will bring you directly in Piazza del Duomo, and will drop you off right in front of the magnificent Cathedral with its bell tower; after the visit of the square, where you can also admire the Santa Maria della Scala museum and the Palazzo Arcivescovile, with an easy 5 minutes walking you will reach one of the most famous squares in Italy, Piazza del Campo, a brick-paved square where the famous Palio horserace (the most important event of Siena) is held, twice a year. Here you can also see the imposing Town Hall with its Mangia Tower, the Cappella di Piazza, the Gaia Fountain, and all the beautiful palaces surrounding the square.
120 minutes here
Florence
Conclude your experience with a relaxing one hour drive back to your accommodation in Florence, after a day full of memories about the real essence of Tuscany
60 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 8 travelers per booking
- Operated by
- Prestige Rent
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
- Suitable for all physical fitness levels
Photos






What travelers are saying
Outty’s summary of the themes that recur across 66 traveler reviews. Written by us, not quoted from reviewers.
Food and drink
7 mentionsThe tastings and food stops are a highlight for most reviewers.
The guide
6 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
5 mentionsReviewers describe the commentary as informative rather than scripted.
Traveler reviews
66 verified traveler reviews for Private daytrip to Siena & Chianti wine country, with wine tasting from Florence. Ratings and reviews provided by Viator and Tripadvisor.
Great job and wine
Vincenzo and Daniele were awesome
via Tripadvisor
Chianti Classico experience
Amazing!! Daniele and Nino were wonderful hosts and took us to two beautiful wineries in the Chianti Classico region. This was my second time in Florence and I was happy to experience more of the countryside and the group made it easy and fun. It was a perfect half day with wonderful wine and snacks at both stops. It was very interesting to learn what makes Chianti so special and now I know what to look for when I get home. Highly recommend, easy to find and enjoy.
via Tripadvisor
Wonderful Day Trip to Tuscany
Alessia and Alessio were fantastic as guide and driver.
via Tripadvisor
Do not miss out on Chianti
Incredible day trip. Everything about the experience was amazing. Incredible views and wine were the highlight. Our Guide, David, was a wealth of knowledge and our driver, Sergio, expertly navigated the area. We loved everything about our trip.
via Tripadvisor
Fantastic!
Highly recommend this tour. Alessia, our tour guide and Mike, our driver were fantastic. Alessia was incredibly friendly and so knowledgeable of the history of these areas. While in Siena we took the optional tour of the cathedral which was well worth the extra 15 euros each. The lunch and wine tasting at a Tuscan winery was delicious. Free time to roam in San Gimignano was a perfect way to conclude our day. (Mother Nature was great too - about 80 degrees and bright blue skies all day). Simply terrific!
via Tripadvisor
Good to know
- Duration
- 8 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- €163 to €668
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 23
- Verdict
- Exceptional
Who runs this experience
Operated by Prestige Rent, who run 5 experiences we rank across 2 cities, with an average Outty Ranking of 83.5 and 3 in the 90+ Club.
See everything Prestige Rent runsWhy this scores 80
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private daytrip to Siena & Chianti wine country, with wine tasting from Florence: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Private daytrip to Siena & Chianti wine country, with wine tasting from Florence cost?
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Prices start at €163 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 Private daytrip to Siena & Chianti wine country, with wine tasting from Florence take?
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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 Private daytrip to Siena & Chianti wine country, with wine tasting from Florence worth it?
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It holds an Outty Ranking of 80 out of 100, which we label "Exceptional". That score blends traveler sentiment (5/5 across 66 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Florence, and how flexible the cancellation terms are.
Can I cancel or reschedule Private daytrip to Siena & Chianti wine country, with wine tasting 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 Private daytrip to Siena & Chianti wine country, with wine tasting from Florence suitable for kids and families?
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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 Private daytrip to Siena & Chianti wine country, with wine tasting from Florence?
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Around 23 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 8-hour experience runs outdoors or after sunset.
Where does Private daytrip to Siena & Chianti wine country, with wine tasting 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 -by a storyteller, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner, Florence Pizza or Pasta Class with Gelato Making at a Tuscan Farm. 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.
What is included in Private daytrip to Siena & Chianti wine country, with wine tasting from Florence?
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Included: Private transportation; Other; Initial briefing with the driver with explanation of the options, to let you build your pe; Private English-speaking driver, with fully equipped, Mercedes vehicle; and In-vehicle air conditioning. Not included: Guided tour of Siena and entrace fees in Siena (if applicable); and Lunch. Always check the voucher for the final list before you travel.
Does Private daytrip to Siena & Chianti wine country, with wine tasting from Florence include hotel pickup?
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Yes, pickup is offered for every traveler from 440 listed pickup locations in and around Florence. You can also enter a custom pickup address when booking.
What languages is Private daytrip to Siena & Chianti wine country, with wine tasting from Florence offered in?
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It runs in English. 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 daytrip to Siena & Chianti wine country, with wine tasting from Florence?
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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 daytrip to Siena & Chianti wine country, with wine tasting from Florence wheelchair or stroller accessible?
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The operator notes: Infants and small children can ride in a pram or stroller; and Specialized infant seats are available. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to Private daytrip to Siena & Chianti wine country, with wine tasting from Florence if the weather is bad?
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It generally runs rain or shine, so dress for the forecast in Florence. Standard cancellation terms apply: free cancellation up to 24 hours before the start.
What do travelers say about Private daytrip to Siena & Chianti wine country, with wine tasting from Florence?
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Across 66 reviews averaging 5.0 out of 5, recurring themes include food and drink, the guide, knowledge and storytelling. The tastings and food stops are a highlight for most reviewers.
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