Great experience! Our driver was Claudius and he was extremely knowledgeable. Our trip was perfect with Claudius at the wheel!





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.
Prices are per person when two book together; a solo traveller pays $706.
Larger groups pay less per person.
From the operator’s live schedule on Viator, checked Oct 14.
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.
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.
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For a full refund, cancel at least 24 hours before the scheduled departure time.
DeepWine Half Day 2 Wineries & Lunch or Dinner in Tuscan Hills lasts about 4h 30min. The itinerary has 2 stops.
Prices start at $399 per person for this Florence experience, booked through Viator with the price shown before checkout. That is the per-person price when two book together; a solo traveller pays $706. There are 2 booking options, so the final price depends on the option you choose.
According to the operator’s current schedule, it runs every day, starting at 12:30 PM and 4:30 PM.
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
Yes, pickup is offered. Pickup points include Hotel Romagna.
The experience is available in EN.
It is a private experience: only your party takes part. Up to 15 travellers can book together.
Infants and small children can ride in a pram or stroller Specialized infant seats are available
Yes, bookings are confirmed instantly.
Travellers rate it 5.0 out of 5 across 20 reviews on Viator and Tripadvisor; it is run by I Just Drive.
Reviews collected by Viator and Tripadvisor
Great experience! Our driver was Claudius and he was extremely knowledgeable. Our trip was perfect with Claudius at the wheel!
Excellent experience. Gabrielle is very professional and provided great service, helpful guidance and the vehicle was very comfortable. 100% recommended. Wine tasty experience and Tuscany landscape make this tour unforgettable
⭐⭐⭐⭐⭐ Amazing Tuscany Experience with Diana! We had an absolutely wonderful all-day tour of Tuscany with Diana from TrueScany. It was one of the highlights of our trip to Italy. The day was a perfect combination of everything we wanted to experience—beautiful Tuscan countryside, a fantastic wine vineyard, Pisa, and charming medieval villages. The scenery throughout the day was incredible, with breathtaking views of the rolling hills and vineyards that Tuscany is famous for. Diana was friendly, knowledgeable, and made the entire day enjoyable and relaxing. She shared interesting information about the history, culture, wine, and villages without ever making the tour feel rushed. The vineyard experience was especially memorable, and visiting Pisa and the medieval villages made the day feel like we experienced several different sides of Tuscany in one tour. If you're visiting Florence or Tuscany and want a full-day experience that combines wine, history, beautiful villages, and spectacular scenery, I highly recommend Diana and TrueScany. A fantastic day and absolutely worth it!
Gabriele was a great guide and did a tremendous job explaining everything
Everything 5 stars! We really liked the experience! Thank you for the kindness!
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!
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!
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.
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.
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!!
| Tour | Duration | Rating | Price | |
|---|---|---|---|---|
DeepWine Half Day 2 Wineries & Lunch or Dinner in Tuscan Hills | 4h 30min | 5.0 (20) | $399 | |
Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner | 8 hours | 5.0 (1,593) | $170 | View |
It's Wine Time! 2 wineries & farm-to-table lunch—max 8 pp | 5h 30min | 5.0 (120) | $256 | View |
Chianti Delights: Tuscan Tale Of 2 Wineries With Vineyard Dinner | 7h 30min | 4.1 (345) | $101 | View |
Half-Day Chianti Tour to 2 Wineries with Wine Tastings and Meal | 5h 30min | 4.9 (55) | $273 | View |
Tuscany Winery Hopping Tour with Lunch & Tastings at 2 Vineyards | 5 hours | 4.8 (108) | $101 | View |
"Good Morning Chianti Classico" - Tour in 2 wineries with lunch | 6 hours | 5.0 (2) | $205 | View |