DeepWine Half Day 2 Wineries & Lunch or Dinner in Tuscan Hills
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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 16 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is DeepWine Half Day 2 Wineries & Lunch or Dinner in Tuscan Hills worth booking?
DeepWine Half Day 2 Wineries & Lunch or Dinner in Tuscan Hills is a 4.5-hour experience in Florence, Italy, from $148 per person. It scores 66 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 5/5 rating across 16 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 66 / 100
- Rating
- 5/5 (16)
- Duration
- 4.5 hours
- From
- $148 per person
Private DeepWine Chianti – A Taste of Tuscany Like No Other Join us for an unforgettable journey through the rolling hills of Chianti, just outside Florence. This intimate day trip takes you deep into the heart of Tusca
What you get
About this experience
Private DeepWine Chianti – A Taste of Tuscany Like No Other Join us for an unforgettable journey through the rolling hills of Chianti, just outside Florence. This intimate day trip takes you deep into the heart of Tuscany's most iconic wine region, where passion, tradition, and flavor come together. Visit two charming, family-run wineries, where you'll be welcomed like an old friend. Explore their ancient cellars, hear the stories behind generations of winemaking, and enjoy guided tastings of their finest Chianti wines and extra-virgin olive oil. Then, sit down for a hearty Tuscan meal, homemade and bursting with local flavors — the kind of light lunch you’ll remember for a long time. And of course... let the atmosphere do the rest: cypress-lined roads, golden vineyards, and the warmth of true Tuscan hospitality. Whether you're a wine lover or just someone who enjoys the good life, this is more than a tour — it's a sensory experience.
What's included
Included
- Guided visit of two different Chianti wineries
- Bottled water
- Hotel pick up and drop off is included within the pickup zone
- Alcoholic beverages
- Wine tasting and extra-virgin olive oil tasting
- Lunch
- Private transportation
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
Ginestra Fiorentina
First winery Immerse yourself in the splendid Tuscan landscape, be captured by the beauty and uniqueness of the rolling hills of the Chianti region with the characteristic cypress trees, the renowned vineyards and the wonderful olive trees. Rediscover the true flavours of the past and relive the ancient traditions. Typical recipes are preserved with great pride and attachment to the territory, the wine is produced with great passion and with traditional methods of great respect for the soil and nature - Wine tour, tasting and light lunch. Second Winery The unique environment of this wineryi, with its rich biodiversity, makes this charming estate in the heart of Chianti a one-of-a-kind place to rediscover flavors, aromas, and the authenticity of an almost forgotten way of life.
210 minutes here
San Michele a Torri
At the second stop arrive at a beautiful estate surrounded by olive trees and vines. You’ll enjoy a guided wine tasting and sample high-quality extra virgin olive oil, while learning about the region’s rich agricultural heritage and time-honored production methods.
55 minutes here
Where it starts and ends
Meeting point
Florence
Hotel pickup
Pickup is available for selected locations. Pickup begins about 10 minutes before departure.
Ends at
Returns to the starting point
Options you can book
Private DeepWine Half Day 2 Wineries & Lunch in Tuscan Hills
Wine tour, tasting and Lunch Pickup included
Afternoon 2 Wineries & Dinner
Wine tour, tasting and Dinner 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 15 travelers per booking
- Operated by
- I Just Drive
Know before you go
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Specialized infant seats are available
- Suitable for all physical fitness levels
- A maximum of 8 people per each Mercedes van
- Operates rain or shine
Photos
What travelers are saying
Outty’s summary of the themes that recur across 15 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
7 mentionsThe tastings and food stops are a highlight for most reviewers.
Traveler reviews
15 verified traveler reviews for DeepWine Half Day 2 Wineries & Lunch or Dinner in Tuscan Hills. Ratings and reviews provided by Viator and Tripadvisor.
Great Full Day Tour!
We had an absolutely incredible full-day Tuscany tour with Truescany, and Claudius made the entire experience! He was personable, funny, knowledgeable, and genuinely such a pleasure to spend the day with. We got an early start, and Claudius first took us to Piazzale Michelangelo for the beautiful views over Florence. From there, we headed to San Gimignano, which was incredible and one of our favorite stops. We had a few hours to wander around, shop, and explore on our own before continuing into the Tuscan countryside. We then visited two very different wineries. The first was a larger winery where we had an incredible lunch paired with a very generous and extensive wine tasting. The food, wine, and setting were fantastic. Our second stop was a smaller organic winery on a property dating back to the 1300s. It was completely different from the first and so cool to experience. We loved getting to see both sides of winemaking in the region. This was easily one of the best days of our trip to Italy. We cannot recommend Truescany enough, and if you can request Claudius as your driver, absolutely do it. 10/10 day and an experience we’ll remember for a long time!
via Tripadvisor
Excellent experience
We had a lovely experience at the two wineries, both were very different, lunch was delicious. Individuals were very patient with our large group and ensured we had a lovely experience. Very educational and a joy to your grounds and cellars etc. We had an absolutely fantastic experience with Marco and couldn’t recommend him highly enough. From start to finish, he was incredibly professional, reliable and always prompt when picking us up. We were travelling as a large group, which isn’t always the easiest to manage, but Marco was exceptionally patient, accommodating and made everything feel effortless. He was always friendly and welcoming, and nothing ever seemed too much trouble. What made the experience even better was Marco’s knowledge of the local area. He shared lots of useful information, recommendations and insights along the way, which really added to our trip. Marco is a true professional and provided an excellent service throughout. His punctuality, patience and friendly manner made such a difference to our experience. We wouldn’t hesitate to use him again and would highly recommend him to anyone looking for a reliable and knowledgeable driver. Thank you, Marco, for looking after us so well!
via Tripadvisor
Amazing
Claudius was very personable and made our van ride enjoyable! Both wineries were amazing. Very informative. Totally recommend this trip and have Claudius as a driver. He is the best.
via Tripadvisor
Great experience!!!
The communication before was great. I knew exactly where the pickup was and pickup went perfectly. Andrea picked us up and was an awesome host!!! He knew the area so well and had tremendous knowledge of the local wineries. It also helped that he had a great sense of humor and really made us all feel comfortable. The two wineries were phenomenal and the food was fantastic. Highly recommend this for anyone that wants wine tasting, good food, and a great host.
via Tripadvisor
Personalized Tuscany experience
Claudius (and his trainee Marco!) was absolutely amazing! On the way to the wineries, he showed us the amazing look out spots and continued to provide history and color for the region. Absolutely recommend!!
via Tripadvisor
Good to know
- Duration
- 4.5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $148 to $620
- Hotel pickup
- Available for selected locations
- Booked in 30 days
- 6
- Verdict
- Solid Choice
Why this scores 66
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
DeepWine Half Day 2 Wineries & Lunch or Dinner in Tuscan Hills: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does DeepWine Half Day 2 Wineries & Lunch or Dinner in Tuscan Hills cost?
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Prices start at $148 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 DeepWine Half Day 2 Wineries & Lunch or Dinner in Tuscan Hills take?
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Plan for about 4.5 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 DeepWine Half Day 2 Wineries & Lunch or Dinner in Tuscan Hills worth it?
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It holds an Outty Ranking of 66 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 16 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 DeepWine Half Day 2 Wineries & Lunch or Dinner in Tuscan Hills?
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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 DeepWine Half Day 2 Wineries & Lunch or Dinner in Tuscan Hills suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 4.5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book DeepWine Half Day 2 Wineries & Lunch or Dinner in Tuscan Hills?
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Around 6 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 4.5-hour experience runs outdoors or after sunset.
Where does DeepWine Half Day 2 Wineries & Lunch or Dinner in Tuscan Hills 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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