Setting out on a horseback ride through the rolling Tuscan hills is an exhilarating way to experience the region’s natural beauty. Visitors can marvel at the picturesque vineyards and medieval charm of San Gimignano before indulging in a three-course lunch paired with local wines and olive oil at a renowned Chianti winery. This comprehensive tour offers an opportunity to take in the cultural and culinary delights of Tuscany. With transportation included and an English-speaking guide, guests can sit back, relax, and let the magic of this enchanting destination unfold before them.
Key Points

- Guided horseback riding through the picturesque Tuscan countryside, offering a unique perspective to explore rolling hills and vineyards.
- Guided visit to the UNESCO World Heritage Site of San Gimignano, exploring its well-preserved medieval architecture and cultural heritage.
- Authentic three-course Tuscan meal at a Chianti winery, with a selection of locally-produced wines expertly paired with the dishes.
- Tasting of a Chianti Classico, Sangiovese, Montepulciano, and Brunello di Montalcino, along with the winery’s celebrated extra virgin olive oil.
- Small-group tour size (up to 8 participants) with an informative English-speaking guide, providing personalized attention and insights throughout the experience.
Transportation Included
The tour provides roundtrip transportation by a comfortable 8-seater minivan, with hotel pickup and drop-off included. Travelers won’t have to worry about navigating the roads or finding parking.
The air-conditioned vehicle ensures a comfortable journey to and from the tour’s destinations. Whether you’re staying at a hotel or private accommodation, the tour company will pick you up and return you to your starting point at the end of the day.
This convenient transportation service allows you to fully learn about the Tuscan countryside without the hassle of driving. With the logistics taken care of, you can simply sit back, relax, and enjoy the scenic ride.
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Horseback Riding Experience

During the tour, participants enjoy a 1-hour horseback ride through the picturesque Tuscan countryside.
Before the ride, they receive a pre-ride orientation and are provided with a helmet to ensure their safety and comfort throughout the experience.
The guided horseback ride allows travelers to enjoy the natural beauty of the region, providing a unique perspective as they explore the rolling hills and vineyards.
The horseback riding experience includes:
- A pre-ride safety briefing
- Helmet provided for each participant
- Guided tour through the stunning Tuscan landscape
- Opportunity to connect with the majestic horses
- An unforgettable way to explore the countryside
Medieval Town of San Gimignano

Following the horseback riding experience, participants embark on a guided visit to the medieval town of San Gimignano.
This UNESCO World Heritage Site, renowned for its well-preserved towers and historic architecture, offers a glimpse into the rich cultural heritage of Tuscany. Strolling through the charming streets, visitors can admire the iconic skyline, adorned with the iconic towers that once served as symbols of power and wealth.
The guided tour provides insights into the town’s history, allowing participants to enjoy the medieval atmosphere and gain a deeper appreciation for the region’s past. With the opportunity to explore the local shops and purchase authentic Tuscan products, the visit to San Gimignano complements the overall experience of the tour.
Opportunity to Purchase Local Products
Visitors can take advantage of the opportunity to purchase authentic Tuscan products during the guided visit to San Gimignano. The medieval town is known for its diverse array of local shops, where travelers can find a wide selection of artisanal goods, including olive oil, wine, cheese, and handmade crafts. The tour allows time for browsing and purchasing some of these local specialties.
Visitors may choose to:
- Explore the charming shops and markets of San Gimignano
- Sample and purchase award-winning Chianti wines
- Buy locally produced olive oils and balsamic vinegars
- Discover handcrafted ceramics, textiles, and leather goods
- Ship their purchases back home to enjoy a taste of Tuscany
Authentic Tuscan Wine Pairing Lunch

The tour includes an authentic three-course Tuscan wine pairing lunch at a Chianti winery, where visitors can savor the flavors of the region.
During this meal, guests will have the opportunity to taste a selection of wines and olive oil produced by the winery. The lunch features traditional Tuscan dishes, expertly paired with the locally-sourced wines to enhance the flavors of both.
This culinary experience allows participants to enjoy the rich gastronomic heritage of Tuscany. The knowledgeable tour guide is on hand to provide insights into the winemaking process and the history behind the menu items.
This lunch is a highlight of the tour, offering a truly authentic taste of Tuscan cuisine.
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Winery Tasting of Wines and Olive Oil

During the Tuscan wine pairing lunch, participants savor a tasting of the winery’s selection of wines and olive oil.
The knowledgeable tour guide provides insights into the winemaking process and the history behind these locally-sourced products, enhancing your’ appreciation of the regional flavors.
The tasting features:
- A crisp, light-bodied Chianti Classico
- A robust, full-bodied Sangiovese
- A smooth, fruity Montepulciano
- A bold, peppery Brunello di Montalcino
- The winery’s signature extra virgin olive oil, celebrated for its balanced acidity and herbaceous notes.
Guests delight in discovering the nuanced flavors and learn how the unique terroir of Chianti shapes the character of these renowned Tuscan specialties.
Informative English-speaking Tour Guide
The tour guide’s extensive knowledge of the region’s history and culture enhances participants’ appreciation of the Tuscan experience. As an informative English-speaking guide, they provide valuable insights throughout the tour.
Sharing fascinating details about the medieval town of San Gimignano, the guide brings the destination to life, explaining its architecture, traditions, and significance.
Plus, the guide offers expert commentary on the winemaking process and olive oil production at the Chianti winery, enriching the tasting experience.
With their engaging narrative and attentive care, the guide ensures the tour is both educational and enjoyable, leaving participants with a deeper understanding and cherished memories of Tuscany.
Small-group Tour Size
With a small-group size limited to eight participants, the tour offers a more intimate and personalized experience. This allows the guide to provide focused attention to each guest, addressing their individual interests and questions throughout the excursion. The small group size also facilitates easier navigation through the medieval streets of San Gimignano and enhances the overall interaction and camaraderie among the travelers.
Some additional benefits of the small-group format include:
- Opportunities for more meaningful conversations with the guide and fellow participants
- Flexibility to adjust the pace and itinerary based on the group’s preferences
- Reduced wait times and less crowding at the winery and other sites
- Personalized recommendations for local products and souvenirs
- A heightened sense of exclusivity and immersion in the Tuscan experience.
Frequently Asked Questions
Is the Tour Suitable for People With Disabilities?
The tour may not be suitable for people with disabilities as it involves horseback riding and hiking in a medieval town. However, the tour provider may be able to accommodate specific needs upon request.
Can I Bring My Own Food and Drinks on the Tour?
The tour does not allow guests to bring their own food or drinks. A full lunch and wine tasting are provided at a Chianti winery as part of the tour experience.
Are There Any Age Restrictions for the Horseback Riding Activity?
The tour has no specific age restrictions for the horseback riding activity. However, it’s recommended that participants be comfortable around horses and able to follow safety instructions from the guide. Riders must wear a provided helmet for the duration of the ride.
Can I Customize the Tour to My Preferences?
Yes, travelers can customize the tour to their preferences. The tour operator offers flexibility to accommodate dietary needs and modify activities upon request. However, advance notice is required to ensure a seamless experience.
What Is the Cancellation and Refund Policy for This Tour?
The cancellation and refund policy allows full refunds for cancellations up to 24 hours before the tour. Shorter notice may incur fees. Customers should review the policy before booking to understand the terms.
Recap
Discover the beauty of Tuscany on this captivating horseback riding adventure.
Explore the medieval town of San Gimignano and savor a delicious three-course lunch paired with a selection of locally produced wines and olive oil at a renowned Chianti winery.
With transportation included and an informative English-speaking guide, this small-group tour offers an unforgettable blend of adventure, culture, and culinary delights.
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