Horseback Ride in S.Gimignano with Tuscan Lunch Chianti Tasting

Experience the Best of Tuscan Countryside with a Horseback Ride, Chianti Wine Tasting, and San Gimignano

If you’re dreaming of experiencing Tuscany’s rolling hills, vineyards, and historic towns all in one day, this tour offers a well-balanced mix of adventure, culture, and culinary delights. For $220.60 per person, you’ll spend about eight hours exploring the scenic countryside on horseback, wandering through the medieval streets of San Gimignano, and enjoying a Tuscan lunch paired with local wines. The tour departs from Florence early in the morning, ensuring you make the most of your day in this picture-perfect region.

What makes this experience stand out is the attention to detail—your guide provides a gentle horse and riding gear suitable for beginners, making the ride accessible even if you’re new to horseback riding. Plus, the chance to combine outdoor activity with a guided town visit and wine tasting means you’re getting a well-rounded taste of Tuscany.

However, a potential consideration is that the group size is limited to just eight people, which is great for intimacy but requires booking in advance (on average, 52 days ahead). Also, note that hotel pickup and drop-off are not included, so you’ll need to plan your transportation to the meeting point in Florence.

This tour suits travelers who appreciate authentic experiences, enjoy scenic outdoor activities, and want to discover Tuscany’s culinary and historical treasures without feeling rushed. It’s perfect for those who love a blend of gentle adventure, picturesque towns, and good food.

Key Points

• Authentic Tuscan scenery: Ride through vineyards, olive groves, and rolling hills of Chianti.
• Balanced itinerary: Combines horseback riding, town exploration, and wine tasting.
• Small group size: Limited to 8 participants, ensuring a personal experience.
• Expert guides: Knowledgeable guides like Lorenzo and Tomas enhance the experience.
• Flexible options: Can substitute a farm tour for the horseback ride if preferred.
• Excellent reviews: Consistently rated 4.9/5 with glowing feedback.

Discovering Tuscany’s Charms: A Complete Breakdown of the Tour

Starting Point and Transportation

Your day begins early at Via Curtatone in Florence, where a comfortable AC 8-seater minivan will pick you up. The ride to the countryside offers a chance to enjoy the scenic drive, with some guides sharing interesting tidbits about the region even before you arrive. The fact that transportation is included is a big plus, removing the hassle of navigating by yourself and allowing you to relax and soak in the views.

The Horseback Ride: 1 Hour of Scenic Leisure

Once at the ranch, you’ll meet your friendly guide, who provides a pre-ride orientation along with a helmet and insurance. The horseback riding experience is designed to be accessible, even for beginners, and the horses are well-behaved and accustomed to newcomers. As one reviewer, Teresa, puts it, “Great experience being able to ride the horses while overlooking Tuscany’s vineyards and beautiful rolling hills.”

Expect to ride through olive groves and vineyards, with plenty of opportunities for great photos. The ride lasts about an hour, making it a perfect balance between fun and manageable for most people. Multiple reviews praise the spectacular scenery and the knowledgeable, friendly guides who go out of their way to make sure everyone is comfortable.

Exploring San Gimignano: Medieval Charm and Gelato

After the ride, there’s about 1.5 hours scheduled for exploring the medieval town of San Gimignano. This UNESCO World Heritage Site is famous for its towers and well-preserved medieval architecture. You’ll enjoy a guided walk through the main squares, where the narrow streets and panoramic views evoke a sense of stepping back in time.

Many visitors rave about the delicious homemade gelato by Dondoli, a world-championship-winning gelateria. As one reviewer states, “San Gimignano is so charming, and the gelato is simply the best.” You’ll have free time to shop for local products, enjoy the scenery, or simply soak in the atmosphere of this historic hilltop town.

Tuscan Light Lunch & Wine Tasting

The afternoon features a delicious Tuscan light lunch paired with wine at a Chianti winery. Expect a guided tasting session of local wines and extra virgin olive oil produced on the estate. The lunch offers a chance to indulge in authentic regional flavors, with vegetarian, vegan, and gluten-free options available upon request.

Reviewers highlight the generous wine tasting—many say it’s enough to truly appreciate the region’s flavors. The value of this part of the tour is high, considering the quality of the food, the wines, and the insight provided about the production process. It’s a perfect way to slow down and enjoy the flavors that make Tuscan cuisine famous.

Final Return and Reflection

The tour wraps up back at the original meeting point in Florence around 5 p.m., giving you a full day’s worth of activities packed with memorable sights, tastes, and experiences. The small group size ensures you won’t feel lost in a crowd, and the guide’s knowledge makes each stop more meaningful.

Authenticity and Value: Why This Tour Works

What makes this tour stand out is the combination of gentle outdoor adventure, cultural exploration, and culinary delights—all in a manageable, well-organized package. Travelers consistently praise the knowledgeable guides, who add depth with historical insights and personal touches. The spectacular views and authentic local food and wine deliver a genuine taste of Tuscany, far from tourist traps.

Though the cost is slightly above some other day trips from Florence, many reviewers feel the experience offers excellent value for money. The small group size adds to the feeling of exclusivity and personal attention, and the variety of activities keeps the day lively and engaging.

A Few Considerations

The main drawback some travelers mention is that parking might be tricky at the meeting point, so arriving early is a good idea. Also, if the weather turns rainy, the horseback riding could be stressful for the horses and riders, so it’s wise to check the forecast and consider that in your plans.

Who Should Book This Tour?

This experience suits beginners to intermediate riders, as the ride is gentle and designed for all levels. It’s ideal for food lovers, history buffs, and outdoor enthusiasts looking for a comprehensive taste of Tuscany in one day. If you’re eager to see medieval architecture, sample authentic wines, and enjoy scenic landscapes without overexerting, this tour is a fantastic choice.

Travelers who prioritize small-group intimacy and personalized attention will find this tour particularly appealing. It’s perfect for couples, small groups of friends, or anyone who wants a relaxed yet immersive day in Tuscany.

FAQ

Is hotel pickup included?
No, hotel pickup and drop-off are not part of this tour. You’ll need to meet at the designated location in Florence, but the meeting point is near public transportation.

Can kids participate in the horseback ride?
Yes, children over 6 years old can ride if they are taller than 1.10 meters. The ride is gentle and suitable for beginners, making it accessible for most families.

What should I wear for the horseback riding?
Comfortable, casual clothing is fine, and don’t forget closed-toe shoes. Helmets are provided, and you’ll get a pre-ride orientation to help you feel comfortable.

Are vegetarian or gluten-free meals available?
Yes, special dietary requests like vegetarian, vegan, or gluten-free meals can be arranged upon request, ensuring everyone enjoys the lunch.

What happens if the weather is bad?
The tour requires good weather. If canceled due to rain or storms, you’ll be offered a different date or a full refund. Rain may impact the horseback riding experience, so check the forecast beforehand.

How long is the horseback ride?
The ride lasts approximately one hour, which is manageable for most people and offers plenty of photo opportunities.

Final Thoughts

This tour balances adventure, culture, and gastronomy in a way that captures what makes Tuscany special. From the scenic horseback ride to the historic streets of San Gimignano and the delicious wine and food at a Chianti winery, every element is designed to give you a genuine taste of Italy’s heartland.

The small group size and expert guides make it a comfortable, personalized experience that’s suitable for first-timers and seasoned travelers alike. While it does require some planning around transportation, the richness of the sights, flavors, and scenery more than justifies the effort.

If you’re looking for a day trip that offers authentic Tuscan scenery, delicious food, and a little outdoor adventure, this experience is hard to beat. It’s a perfect way to create lasting memories in one of Italy’s most iconic regions, especially if you want to avoid crowded tourist traps and enjoy a more intimate exploration.

Whether you’re a wine enthusiast, a history lover, or simply seeking a relaxing day amidst stunning landscapes, this tour offers a balanced and memorable way to experience Tuscany’s best.