Nestled in the heart of Tuscany, the Chianti region boasts over 8,000 hectares of vineyards, producing some of the world’s most renowned wines.
Imagine strolling through these picturesque vineyards, feeling the gentle breeze on your skin, and soaking in the breathtaking views of the rolling hills. But this experience offers more than just scenic beauty; it’s an opportunity to learn about the rich history and culture of this legendary wine-producing area.
Each twist and turn of the journey reveals surprises waiting to be discovered, making it a truly unforgettable exploration.
Good To Know

- Explore the charming Chianti region with a visit to a family-run winery and lunch at a traditional Tuscan farm.
- Enjoy 2 wine tastings paired with local cuisine, experiencing the rich flavors of the area.
- Discover Monteriggioni Castle and wander the medieval streets of San Gimignano for a culture.
- Travel in a comfortable 7-seater minivan with an English-speaking driver, providing a stress-free and scenic journey.
Tour Highlights

Set out on a journey through the picturesque Chianti region of Siena, Italy, where you’ll discover the charm of a family-run winery, explore the historic Monteriggioni Castle, and wander the medieval streets of San Gimignano.
The tour highlights include visits to local wineries where guests can savor the rich flavors of Tuscan wines and learn about the winemaking process firsthand.
On top of that, exploring historic landmarks like Monteriggioni Castle provides a glimpse into the region’s storied past, offering panoramic views of the rolling hills.
Walking through the narrow, cobbled streets of San Gimignano allows travelers to enjoy the medieval ambiance of this well-preserved town, known for its iconic towers and artisanal shops.
This excursion promises a blend of culture and scenic beauty.
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Pickup and Transportation Details
Upon your scheduled tour date, an English-speaking driver will greet you at your designated location, displaying a welcoming sign, ready to whisk you away in a comfortable 7-seater minivan to kickstart your exploration of the Chianti region.
Vehicle Comfort: Enjoy a smooth ride in a spacious and cozy 7-seater minivan.
English-Speaking Driver: Your knowledgeable driver will be fluent in English, providing insights along the journey.
Free Pickup: Convenient pick-up service available at private addresses, apartments, or B&B within the indicated province.
Comfortable Journey: Relax in the plush seats of the minivan as you travel through the picturesque Chianti countryside.
On-Time Departure: Start your adventure promptly at 09:00 am for a full day of discovery in Chianti.
Inclusions and Exclusions

As you embark on your exploration of the Chianti region, it’s important to understand what’s included and excluded in this immersive tour experience.
The tour encompasses various elements to ensure a delightful journey through the rolling hills. Included are private tours of the Chianti region, visits to off-the-beaten-path attractions, a lunch experience at a traditional Tuscan farm, and 2 wine tastings at different farm wineries. Indulge in a 3-course lunch menu filled with Tuscan specialties and enjoy the convenience of private Wi-Fi-equipped transportation throughout.
What’s not included are the services of a professional guide (available upon request) and any additional items not specified in the inclusions. Prepare to be immersed in wine pairings and culinary delights as you traverse this picturesque region.
What to Expect During the Tour

Visitors can anticipate a personalized journey filled with scenic views, culinary delights, and exclusive wine tastings during the tour through the Chianti region.
- Wine pairings with local cuisine
- Scenic vineyards and historic charm
- Engaging interactions with family-run wineries
- Exploring Monteriggioni Castle and San Gimignano
- Immersive experiences in off-the-beaten-path locations
The tour promises a delightful blend of cultural exploration, gastronomic adventures, and the chance to savor some of the finest wines the region has to offer. Guests can look forward to a day filled with unique flavors, breathtaking landscapes, and a deeper understanding of Chianti’s rich heritage.
Additional Information and Directions

Guests on the tour will receive detailed information and directions for the upcoming experiences in the Chianti region. The tour offers free cancellation up to 24 hours before the experience for added flexibility. Travelers can reserve now and pay later, providing payment flexibility. This ensures that participants can plan their trip with peace of mind, knowing they have the option to change their plans if needed.
Plus, the tour includes private transportation, making it convenient for guests to relax and enjoy the beautiful landscapes of Chianti without worrying about logistics. With these features in place, guests can look forward to a stress-free and enjoyable exploration of the rolling hills and vineyards of Chianti.
More tours and activities we've covered in Siena
- From Siena: Brunello Di Montalcino Guided Wine Tour W/ Lunch
- Brunello Di Montalcino Wine Tour of 2 Wineries With Pairing Lunch
- Vespa Tour With Lunch&Chianti Winery From Siena
- Chianti and San Gimignano – 2 Wineries With Pairing Lunch
- Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle
- Vintage Fiat 500 Tour From Siena: Tuscan Hills and Winery Lunch
Frequently Asked Questions

Can Children Participate in the Wine Tastings During the Tour?
Children can’t partake in wine tastings due to legal restrictions. However, this tour offers family-friendly activities like exploring the Chianti region and enjoying a cultural experience at a traditional Tuscan farm. Child-friendly options and a private tour ensure an enjoyable time.
Are Vegetarian or Vegan Meal Options Available for Lunch at the Traditional Tuscan Farm?
Vegetarian and vegan meal options are available for lunch at the traditional Tuscan farm. Guests with dietary restrictions can savor local cuisine while immersing in the farm experience. It ensures a delightful culinary journey for all.
Is There a Restroom on Board the Private Wi-Fi-Equipped Transportation?
The private Wi-Fi-equipped transportation for the Chianti tour does not have a restroom on board. However, it offers comfortable seating and modern amenities. Guests can enjoy the scenic journey with peace of mind and convenience.
Can Guests Purchase Additional Bottles of Wine From the Wineries Visited During the Tour?
Guests can purchase additional bottles of wine from the wineries visited during the tour. They have the opportunity to acquire wine souvenirs and winery purchases, perfect for taking home tasting exclusives and tour memorabilia with them.
Are There Any Optional Activities or Attractions That Can Be Added to the Tour Itinerary for an Additional Cost?
While exploring Chianti, guests have the opportunity to enrich their experience with optional excursions like vineyard tours, olive oil tastings, or visits to historic sites. These supplemental experiences can be added for an extra cost.
The Sum Up

Set out on a journey through the enchanting landscapes of Chianti, Italy, and experience the perfect blend of culture, history, and gastronomy.
With two wine tastings, a delicious lunch, and visits to hidden gems like Monteriggioni Castle and San Gimignano, this tour promises a memorable and intimate adventure.
Sit back, relax, and let the beauty of Tuscany captivate your senses on this exclusive excursion.
More Lunch Experiences in Siena
- Cooking Class: Italian Authentic Recipes with Lunch
- Classic: Tuscan Vineyard Lunch with Wine Tasting
- VIP Chianti, Brunello wine & Pienza with lunch From Siena
- Siena: Winery Tour, Wine Tasting and Lunch
- Private Art & Wine Tour in Cortona & Montepulciano, With Lunch & 2 Wine Tastings
- Transfer Siena-Pisa With Stop in San Gimignano & Lunch
More Wine Tours in Siena
- Classic: Tuscan Vineyard Lunch with Wine Tasting
- Chianti Wines and San Gimignano Tour from Florence (1 Winery)
- Cook Pasta, Wine-Braised Meat & Dessert (Includes 4-Course Meal)
- Chianti: Wine and Olive Oil Tasting with Cellar Tour
- Siena: Wine tasting Experience with Tuscan Sparkling Wines
- Siena Wine & Gelato tasting
More Tour Reviews in Siena
- Siena: Civic Museum and Palazzo Pubblico Entry Ticket
- Ape Calessino Tour through Tuscan Landscapes
- Siena Small group Cooking Class in a Chianti Farm
- Siena Private Tour Highlights and Hidden Gems with a Local
- Siena Street Food Tour With A Local Guide
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Looking for something different? Other Siena activities we've written about
- Siena: Civic Museum and Palazzo Pubblico Entry Ticket
- Ape Calessino Tour through Tuscan Landscapes
- Siena Small group Cooking Class in a Chianti Farm
- Siena Private Tour Highlights and Hidden Gems with a Local
- Siena Street Food Tour With A Local Guide
- Cook Pasta, Peposo & Tiramisu in a Tuscan Castle (4-Course Meal)
- Florence Walking Tour from Siena with Train Tickets Included
- Cooking Class: Italian Authentic Recipes with Lunch
- Classic: Tuscan Vineyard Lunch with Wine Tasting
- Chianti E-Bike Tour from Siena
- Chianti Wines and San Gimignano Tour from Florence (1 Winery)
- Cook Pasta, Wine-Braised Meat & Dessert (Includes 4-Course Meal)
