"We had a great day visiting 3 locations in Tuscany. San Gimignano in the morning was magical! The lunch and wine tasting were fabulous. We had a smooth ride. Sandru is a fabulous guide - full of energy and information. We had a lovely guide in Siena as well but didn’t get her name. Thank you!"
Wine Tour · Chianti
Best Chianti Wine Tours 2026 — From Florence with Tastings
Taste Sangiovese where it's grown — a Chianti wine tour from Florence with cellar tastings, a Tuscan lunch, and the medieval towers of San Gimignano between the vines.
#1 selling day trip
From
$92
per person
Free cancellation
- 15 Categories All Italian Experiences
- English Guides Local Experts
- Free Cancellation
The Experience
What Makes This Italian Food Experience Special
Everything that makes this a must-book Italian food experience.
Highlights
- Discover the medieval charm of San Gimignano’s ancient towers
- Explore Monteriggioni, a perfectly preserved walled village
- Enjoy a guided tour through Siena’s historic center and Cathedral
- Savor an authentic Chianti wine tasting at a local Tuscan winery
- Delight in a farm-to-table 3-course Chianti-style lunch experience
What's Included
- Mutilingual assistance at the meeting point
- Round-trip travel by air-conditioned coach
- Licensed tour escort
- Exclusive Chianti winery experience with vineyard and cellar tour
- Authentic 3-course Tuscan lunch (A gluten free or vegetarian menu is available upon request)
- Guided tasting of 3 Chianti wines
- Guided walking tour of Siena with a local expert - Monolingual from April to October (if option selected)
- Skip-the-line entry to Siena Cathedral and the Piccolomini Library with a professional guided tour (if option selected)
How Your Chianti Experience Works
Four steps from booking to a real Chianti food experience.
Book Your Chianti Experience
Reserve online in under a minute — instant confirmation by email, with free cancellation on most experiences up to 24 hours before.
Pick Your Date & Time
Browse live availability and pick the slot that fits your trip — most dates show instant confirmation.
Meet Your Local Host
An Assistant waits for you wearing blue clothing with Caf Tour and Gray Line Logos, at the end of the ramp connecting with the railway station.
Taste the Real Chianti
Discover the medieval charm of San Gimignano’s ancient towers
Photo Gallery
Italian Food Experiences — Through the Lens
Fresh pasta, market stalls, Tuscan vineyards, and truffle hunts — captured by our travelers.
Book Your Experience
Check Availability & Prices
Select your preferred date and time. Instant confirmation — free cancellation up to 24 hours before departure.
Chianti Wine Tours — Compared
How the top pick stacks up — pick the highlighted option to book, or browse alternatives.
| Feature | BEST RATED Top Pick | Alternative | Browse All |
|---|---|---|---|
| Starting Price | From $92/per person | Varies | Varies |
| Rating | 4.6★ (3597) | 4.6+★ | 4.5+★ |
| Format | Guided / small group | Various | All formats |
| Free Cancellation | Yes | Most | Most |
| Best For | Best Chianti + sights | Comparison shoppers | Browsing everything |
| Check Availability | View Options | See All Tours |
More Chianti Wine Tour Options
Compare alternative tours — all with free cancellation and instant confirmation.
From Florence: Siena, San Gimignano, Pisa & Lunch at Winery
Discover the Chianti vineyards and medieval architecture of Siena, San Gimignano, and Pisa on a full-day tour. Depart from Florence and explore Tuscany with an optional lunch and wine.
From Florence: Small Group Wine Tasting Tour to Tuscany
Taste the wines and olive oils of Tuscany on a small group tour from Florence. Drive through the rolling hills and marvel at the olive groves and cypress trees of the coutryside. Visit 2 wineries to sample wine paired with local produce.
Florence: Siena, San Gimignano & Monteriggioni with Tasting
Spend a memorable day in Tuscany! Explore Siena, San Gimignano, and Monteriggioni, and savor Chianti wines amid stunning landscapes.
SMALL GROUP TOUR to Tuscan wineries with lunch or dinner
Taste the true essence of the Tuscan wine region on a small-group tour from Florence, as you visit 3 (or 2) authentic wineries and savor a typical Tuscan lunch (or dinner)
From Florence: Chianti Tour with Two Wine and Food Tastings
Discover authentic Chianti with visits to two organic wineries, guided tastings of Tuscan wines and local snacks, vineyard walks and views. Optional morning cooking class with lunch and wine tasting.
Wine Tour · Chianti
About Chianti Wine Tours
Chianti is the heart of Tuscan wine — the region between Florence and Siena where Sangiovese becomes Chianti Classico. A ‘wine tour Chianti’ is, in practice, a day-trip from Florence: cellar tastings at one or two wineries, a long Tuscan lunch, and usually a stop in San Gimignano or Siena. The terms ‘Chianti wine tour’ and ‘Chianti wine tasting’ tie in volume — both describe the same experience.
Compared with the broader Florence wine tours, Chianti-focused trips spend more time in the cellar and less on sightseeing — the better pick if the wine, not the scenery, is the priority.
Also popular: Florence
Guest Reviews
What Travelers Say
"The trip was great! A very easy day out without feeling rushed or feeling like travel time was long. Coach was comfortable and ride was smooth. Guide Hilary was professional, yet enthusiastic. Lunch and wine at vineyard was excellent. before the trip i was a little fearful due to long duration. but i thoroughly enjoyed myself and wished did not end :)"
"An unforgettable tour to Siena and San Gimignano. Both places were absolutely stunning, full of history, charm, and unique atmosphere. Everything was well organized and the timing was perfect, without feeling rushed. Our tour guide, Sandro, was fantastic — knowledgeable, engaging, and genuinely passionate about what he does. He explained everything clearly, shared interesting stories, and made the whole experience even more enjoyable. Highly recommended for anyone who wants to truly experience these beautiful Tuscan towns."
"Such a fun trip, our guide Marta was very knowledgeable. And our driver Ferdinand was very friendly. A very beautiful day, with very nice wine tastings!"
"This was a perfect trip to enjoy the Tuscan landscape. We never felt rushed for anything and the instructions from our your guide Martha were very clear."
Read all 3597 verified reviews
See All ReviewsReady to Book Your Italian Food Experience?
Pick the right category and city for your trip — cooking class, food tour, wine tasting, truffle hunt, or gelato workshop. Hundreds of tours compared, all with free cancellation. Starting from $92 per person.
Browse Italian Food ExperiencesChianti Wine Tour — FAQ
Everything you need to know before booking a wine tour in Chianti.
Prices start around $92 per person for the top-rated option. Costs vary by group size, duration, and inclusions like wine or lunch.
Most run 2–4 hours. Experiences that add a market tour, lunch, or a farm visit run longer — check each tour's details.
Our top pick is "Florence: S. Gimignano, Siena, Chianti Wine Tasting & Lunch" — rated 4.6/5 from 3597 reviews. See the comparison above for alternatives.
Many are — hands-on classes and active experiences tend to be kid-friendly. Check the minimum age listed on each tour before booking.
Most options include tastings or a full meal, and many include wine. The exact inclusions are listed on each tour.
Often yes, with advance notice — vegetarian is usually easy, vegan and gluten-free vary by operator. Flag it at booking.
Meeting points are central and shown on your voucher after booking. For day-trip wine and truffle experiences, pickup is usually from a central point in the departure city.
1–2 weeks in peak season (spring–autumn). Free cancellation on most tours means booking early is low-risk.
Still have questions? Email us at info@italian-food-tour.com