
Chianti Classico Wine Tasting and Siena Exploration
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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.
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Quick answer
Is Chianti Classico Wine Tasting and Siena Exploration worth booking?
Chianti Classico Wine Tasting and Siena Exploration is a 5-hour experience in Florence, Italy, from $98 per person. It scores 55 out of 100 on the Outty Ranking, which we label “Worth a Look”. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 55 / 100
- Rating
- Not yet rated
- Duration
- 5 hours
- From
- $98 per person
You will have an experienced and skilled English-speaking driver who will safely lead you through an unforgettable half-day experience, allowing you to breathe in the true Tuscan atmosphere. You will be guided through th
What you get
- Private transportation
- Bottled water
- Local expert driver (english/italian speaker)
- Somministrazione bevande alcoliche 21+. Ai minori di 21 anni verranno servite bevande analcoliche.
- Alcoholic beverages
- Veicolo con aria condizionata
About this experience
You will have an experienced and skilled English-speaking driver who will safely lead you through an unforgettable half-day experience, allowing you to breathe in the true Tuscan atmosphere. You will be guided through the Tuscan hills to enjoy the view. You will then arrive at our winery in San Donato in Poggio, in the heart of Chianti Classico, where, after a brief tour, you will taste Vernaccia di San Gimignano, Chianti Classico, IGT, and Supertuscan wines, accompanied by some snacks. After the tasting, we will continue the tour along the Chianti roads and arrive in Siena, the city of the Palio, where you can take a stroll through the historic center and appreciate the Gothic style of the Siena Cathedral.
What's included
Included
- Private transportation
- Bottled water
- Local expert driver (english/italian speaker)
- Somministrazione bevande alcoliche 21+. Ai minori di 21 anni verranno servite bevande analcoliche.
- Alcoholic beverages
- Veicolo con aria condizionata
Not included
- Everything that is not mentioned in the inclusions.
What you'll see and do
San Donato in Poggio
After the desired pick-up, the clients will lead to San Donato in Poggio. They will pass through the small village in Chianti Classico and they can admire the statue of the "Gallo Nero" (the symbol of the region) before heading to the winery.
60 minutes here
The clients will have a small tour of the winery followed by a wine tasting of wines from different production areas (Vernaccia di San Gimignano, Chianti Classico, and IGT Toscana reds) along with some snacks and water. The winery experience will last approximately 1.5 hours.
90 minutes here
Centro Storico di Siena - World Heritage Site
After the tasting, the tour will continue along the roads of the southern region of Chianti Classico, and the clients will be taken to Siena. They will have free time to take photos and stroll around the city.
120 minutes here
Piazzale Michelangelo
Stop at Piazzale Michelangelo, one of the most important squares in Florence, where visitors can enjoy a panoramic view of the city and see the statue of David. The clients can take some photos there.
15 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers.
Ends at
Returns to the starting point
Ends at
Wine tour and tasting
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, it
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 7 travelers per booking
- Operated by
- CANTINE GUIDI 1929
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
- We serve alcoholic beverages only to travelers aged 18 or older. Minors under the age of 18 will be served non-alcoholic beverages.
Photos






Good to know
- Duration
- 5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $98 to $275
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 0
- Verdict
- Worth a Look
Why this scores 55
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Chianti Classico Wine Tasting and Siena Exploration: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Chianti Classico Wine Tasting and Siena Exploration cost?
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Prices start at $98 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 Chianti Classico Wine Tasting and Siena Exploration take?
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Plan for about 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 Chianti Classico Wine Tasting and Siena Exploration worth it?
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It holds an Outty Ranking of 55 out of 100, which we label "Worth a Look". That score blends traveler sentiment (0/5 across 0 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 Chianti Classico Wine Tasting and Siena Exploration?
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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 Chianti Classico Wine Tasting and Siena Exploration suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Chianti Classico Wine Tasting and Siena Exploration?
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Around 0 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 5-hour experience runs outdoors or after sunset.
Where does Chianti Classico Wine Tasting and Siena Exploration 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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