
Semi Private Deep Wine Chianti and San Gimignano from Florence
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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.
Traveler rating
4.9/5
Based on 215 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Semi Private Deep Wine Chianti and San Gimignano from Florence worth booking?
Semi Private Deep Wine Chianti and San Gimignano from Florence is a 8.5-hour experience in Florence, Italy, from $209 per person. It scores 81 out of 100 on the Outty Ranking, which we label “Exceptional”, based on a 4.9/5 rating across 215 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 81 / 100
- Rating
- 4.9/5 (215)
- Duration
- 8.5 hours
- From
- $209 per person
This tour is designed to make your Tuscan wine-tasting dreams come true. You'll be able to see all the classic postcard-perfect landscapes of Tuscany while you travel from one cellar to another. You will visit two wineri
What you get
About this experience
This tour is designed to make your Tuscan wine-tasting dreams come true. You'll be able to see all the classic postcard-perfect landscapes of Tuscany while you travel from one cellar to another. You will visit two wineries and have the opportunity to taste a selection of high-quality Tuscan Chianti wines. Lunch is included. If you're a fan of good wine, excellent food, and landscape photography, you'll love this tour. And you'll also have the chance to visit one of the most beautiful villages in the world: San Gimignano, famous for its majestic towers and delicious ice cream. Our tours feature only black, air-conditioned Mercedes Vans, complete with air conditioning, WiFi, and one unlimited Wi-Fi with Pocket-Sized Hotspot for each couple and one bottle of water for every tour member and of course a Bottle of Prosecco White Wine for a travelling happy hour at the end of the tour!
What's included
Included
- WiFi on board
- Bottled water
- Hotel pick up and drop off is included within the pickup zone
- Wine tasting and olive oil tasting
- Air-conditioned vehicle
- 1 Bottle of Prosecco White Wine per group
- Lunch
- One unlimited Wi-Fi Pocket-Sized Hotspot for each couple. Stay connected throughout your journey.
- Alcoholic beverages
Not included
- Gratuity
- Hotel pick up and drop off out of the pick up zone is available under request for an extra fee
What you'll see and do
Piazzale Michelangelo
We start from the pick up point 8:00 and then drive for 15 minutes towards Piazzale Michelangelo. Piazzale Michelangelo offers a stunning panoramic view of Florence, where you can take in the city in all its glory. The large square is home to a replica of Michelangelo's David in bronze.
15 minutes here
San Gimignano
At 8:30 we'll drive for 01:00 hours towards San Gimignano. We then visit the beautiful walled city, San Gimignano, full of history and charm, famous for its imposing towers and delicious ice cream, this tour will be sure to delight your taste buds. The available time there will be 01:25 hours.
85 minutes here
San Casciano in Val di Pesa
At 10:55 we drive for 50 minutes towards a typical Tuscan farmhouse in the Chianti area. We will travel to the heart of Tuscan wine country, and visit a beautiful farmhouse with a cellar. Here, we will enjoy a delicious Tuscan lunch with amazing regional food and some of the most wines of Italy. This will be a perfect opportunity to relax and enjoy the stunning views of Tuscany countryside. The available time there will be 02:30 hours.
150 minutes here
San Michele a Torri
At 14:30 drive for 25 minutes towards San Michele a Torri where we'll make a final stop at a family run wine estate in the province of Florence, where you will have the opportunity to try other great Chianti wines. Because you can't say you know Chianti if you haven't tried at least 5 or 6 different types of wine from the area. The available time there will be 45 minutes.
45 minutes here
Florence
At 15:50 drive back for 40 minutes, towards the initial pick up point. We will arrive there by 16:30. Well in time to have some more fun during your Florentine afternoon.
Pass by without stopping
Where it starts and ends
Meeting point
Florence
The tour starts at 8:00. Please show up at the meeting point 15 minutes in advance.
Hotel pickup
Pickup is available for selected locations. Pickup begins about 15 minutes before departure.
Ends at
The tour starts at 8:00. Please show up at the meeting point 15 minutes in advance.
Options you can book
Special days
Pickup included
Semi Private Morning Tour
Pickup included
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
- I Just Drive
Know before you go
- Wheelchair accessible
- 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
- A maximum of 8 people per Mercedes van
- Direct pick up and drop off from some hotels locates in the historic center (A zone). For all other locations private residences and B&B the meeting points is: In front of Hotel Boccaccio-Tino Caffè, Via della Scala 59 (one minute walking distance from Santa Maria Novella train station), Florence at 8,00 am. Please arrive 15 minutes before scheduled departure time. If you wish you can have breakfast there, English or continental or just a "cappuccino". As I Just Drive guests at Tino Caffè you are entitled to have a 10% discount.
Photos






What travelers are saying
Outty’s summary of the themes that recur across 215 traveler reviews. Written by us, not quoted from reviewers.
The guide
8 mentionsTravelers single out the guide as the reason the experience works.
Food and drink
7 mentionsThe tastings and food stops are a highlight for most reviewers.
Knowledge and storytelling
6 mentionsReviewers describe the commentary as informative rather than scripted.
Value for money
2 mentionsTravelers feel they got more than they paid for.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
215 verified traveler reviews for Semi Private Deep Wine Chianti and San Gimignano from Florence. Ratings and reviews provided by Viator and Tripadvisor.
Amazing experience from start to finish!
My fiancée and I had an amazing time at the San Gimingnano and Chianti region tour. Our tour guide and driver, Marco, was very knowledgeable about the history of the region and provided great information throughout the entirety of the trip. He really brought the experience to life for us. Marco is very friendly and a great person and was a large part of why the experience was so memorable. As for the wine tasting tours, both vineyards had excellent tours with knowledgeable and friendly guides. The selection of wines provided were excellent to try the regional wines of Chianti. Overall, this was an experience we will never forget and highly encourage anyone to book for your trip to the Tuscany region!
via Tripadvisor
Great Overall Experience, Especially for the Price!
David was our tour guide and was excellent! We got lucky and were the only people on our tour that day, so we got a private tour around Tuscany for a great bargain. Even if you aren’t the only ones, the van is plenty big, has great air conditioning, and the places you go are very exciting! San Grimignano was very nice for the history buffs and the rest of the trip was centered around Tuscan wine and cuisine, both of which are excellent!
via Tripadvisor
Amazing day
Great tour. Marco was absolutely amazing, kind and so knowledgeable. We loved having him as our guide. We will request him for our future tours.
via Tripadvisor
San Gimignano/Winery Tour Must Do
We loved this tour. We had enough time in San Gimignano to stroll around and shop and didn’t feel rushed. The lunch was amazing with several courses and the wineries had fabulous Chianti wine. You will probably want to ship some home kind of good! This tour is worth the price and the small group made it better.
via Viator
This was a lovely tour!...
This was a lovely tour! Our guide was David, who was an absolute joy to ride along with and to learn from. The two wineries were perfect - excellent wine tastings paired with a delicious lunch and selection of Tuscan meats & cheeses. The San Gimignano portion of the trip was not for us as it is really just a place to shop. But if you want to do some shopping, there are a large variety of cute shops and you’d likely enjoy it. Either way that is just a short piece of the tour. Highly recommend both this tour and specifically David!
via Viator
Good to know
- Duration
- 8.5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $209 to $229
- Hotel pickup
- Available for selected locations
- Booked in 30 days
- 75
- Verdict
- Exceptional
Why this scores 81
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Semi Private Deep Wine Chianti and San Gimignano from Florence: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Semi Private Deep Wine Chianti and San Gimignano from Florence cost?
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Prices start at $209 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 Semi Private Deep Wine Chianti and San Gimignano from Florence take?
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Plan for about 8.5 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 Semi Private Deep Wine Chianti and San Gimignano from Florence worth it?
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It holds an Outty Ranking of 81 out of 100, which we label "Exceptional". That score blends traveler sentiment (4.9/5 across 215 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 Semi Private Deep Wine Chianti and San Gimignano 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 Semi Private Deep Wine Chianti and San Gimignano from Florence suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 8.5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Semi Private Deep Wine Chianti and San Gimignano from Florence?
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Around 75 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 8.5-hour experience runs outdoors or after sunset.
Where does Semi Private Deep Wine Chianti and San Gimignano 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 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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