Horseback Ride in S.Gimignano with Tuscan Lunch Chianti Tasting

Exploring Tuscany through a guided horseback ride combined with a traditional lunch and wine experience sounds like a dreamy way to spend a day. This tour, offered from Florence, promises an authentic taste of the region’s scenic landscapes, historic towns, and culinary delights—all in a well-organized, small-group setting.

What immediately catches the eye is the eight-hour itinerary that balances active outdoor fun with cultural sightseeing and delicious food. The fact that this tour is highly rated — sitting at a perfect 5.0 out of 5 from nearly 400 reviews — suggests that many travelers find it to be a standout experience.

One thing to keep in mind: the tour is weather-dependent, so if rain is in the forecast, the experience may be altered or canceled, which reviewers noted. Still, if you love scenic views, good wine, and a relaxed pace, this experience is likely to hit the spot, especially for those who appreciate small-group intimacy and expert guides.

Key Points

• Authentic Tuscan countryside experience with horseback riding, sightseeing, and wine tasting in one day
• Small-group format (max 8 people) ensures personalized attention and a more intimate vibe
• Excellent value for money considering the multiple activities, meals, and tastings included
• Highly praised guides make a difference, with many reviewers mentioning knowledgeable and friendly hosts
• Flexible options available, including substituting a farm tour for the horseback ride if needed
• Ideal for active travelers and food/wine enthusiasts wanting a comprehensive taste of Tuscany

What You Can Expect from This Tour

The Itinerary Breakdown

Start at Florence at 9:00 AM with a comfortable, air-conditioned minivan ride that lasts about 45 minutes to an hour. This is a great way to relax after a morning coffee and get into the mood for the day ahead. The small-group size means that you’re not lost in a crowd, and your guide — often praised for their knowledge and friendliness — quickly makes everyone feel at ease.

Stop 1: Horseback Riding near San Gimignano
The highlight for many: a 1-hour guided horseback ride across Tuscan vineyards and olive groves. Reviewers like Teresa_S appreciated the gentle horses and well-organized pre-ride orientation, noting that the horses were suitable even for beginners. You’ll enjoy a scenic stroll through rolling hills with plenty of photo opportunities.

According to reviews, the ride is about an hour long, and the horses are well-behaved, which is great if you’re new to riding or prefer a relaxed pace. One reviewer mentioned that the horses appeared older and very tired, which could be a consideration for horse enthusiasts, but most found the experience comfortable and enjoyable.

The Scenic Town of San Gimignano
After the ride, you have approximately 1 hour and 30 minutes to explore San Gimignano, a stunning medieval village famous for its towered skyline and panoramic views. Many reviews highlight how charming and photogenic this town is, with its narrow streets and historic architecture.

A personal favorite? Sampling the world-championship-winning gelato by Dondoli, mentioned explicitly by travelers like Kelsey_B. She called it a “perfect sampling of everything Tuscany can offer,” emphasizing the combination of delicious food, hospitality, and stunning scenery.

The Lunch and Wine Tasting
The tour includes a Tuscan light lunch paired with wine at a local Chianti winery. The meal is described as authentic, featuring local ingredients, and paired with a selection of wines and olive oil produced on-site. Several reviewers, including Jennifer_V, called the lunch “amazing,” praising the quality of the food and the friendly, informative guides who lead the wine tasting.

Many guests appreciated the opportunity to buy and ship local products directly from the winery, making it a practical souvenir or gift. The wine tasting itself is guided, giving you insight into the regional varieties, which is a huge plus for oenophiles.

Additional Highlights and Practical Details

• Transportation: Roundtrip transportation in an AC 8-seater minivan means a comfortable, hassle-free ride with a small group, enhancing the intimate feeling.
• Guides: Many reviews highlight the guides’ knowledge and friendliness, with some travelers mentioning guides like Lorenzo and Daniele by name, praising their personal touch and storytelling.
• Group Size: Limited to 8 travelers, which means more personalized attention and a chance to ask questions or customize parts of your experience.
• Meal Options: Vegetarian, vegan, and gluten-free options are available upon request, making this tour accessible for various dietary needs.
• Booking Tip: Most travelers book about 7-8 weeks in advance, as the tour is popular and limited in size.

The Real Value of This Experience

When considering the $220.60 per person cost, many reviewers agree it’s a worthwhile investment. You’re not just paying for a horseback ride; you’re getting a full immersion in Tuscan culture, landscape, and cuisine. The combination of active outdoor fun, cultural exploration in San Gimignano, and a wine and food experience means you’re covering a lot in one day.

Compared to other tours that might focus solely on wine tasting or town visits, this package offers a well-rounded view of Tuscany. The horseback ride makes the scenery tangible and memorable, not just a backdrop for photos but an active part of your day.

The tour’s flexibility — for example, the option to substitute a farm tour for the horseback riding — ensures it can suit different preferences or physical abilities. Plus, the small-group format fosters a relaxed atmosphere, making the experience feel more like a day out with friends than a scripted tour.

The Experience in Practice: What You’ll Love

We loved the variety and authenticity of this tour. The scenic horseback ride, especially, is a real highlight: riding through vineyards and olive groves, with views stretching over the Tuscan hills, is an experience you’ll remember long after you’ve returned home. Reviewers like David_E and Cheryl_G describe it as a “great day” with “beautiful countryside” and “spectacular views.”

The guided visit to San Gimignano is more than just a photo stop. It’s a chance to wander at your own pace, soak in medieval charm, and enjoy local treats. One reviewer called it “a charming, photogenic town,” perfect for wandering and shopping. The gelato by Dondoli, a must-try, is often praised as the best in the world.

The lunch and wine tasting at the Chianti winery is topped off with a chance to learn about regional wines and olive oil, making it both enjoyable and educational. The quality of the food and wine, combined with the warm hospitality, delivers great value.

Potential Drawbacks

While overwhelmingly positive, some reviews mentioned weather dependency. Rain can make the horseback riding more stressful for horses and riders, and the experience might be less enjoyable if mud or slippery conditions develop. Also, parking at the meeting point can be tricky, so arriving early is recommended to avoid stress.

Another point to consider: the horses are described as older and possibly tired by some guests, which could be a concern for riders seeking a more energetic ride. But for most, the gentle pace suits beginners and casual riders perfectly.

Who Should Consider This Tour?

This experience suits active travelers who love scenic landscapes and cultural sites. It’s particularly good for those who want to combine physical activity with gourmet food and wine. If you enjoy a relaxed pace and small-group tours, you’ll appreciate the intimate setting.

Families with older children (over 6 years and taller than 1.10 meters) will find it suitable, especially since the horses are gentle and easy to ride. Foodies and wine lovers will enjoy the pairing at the winery, and history buffs will appreciate the visit to San Gimignano.

Those looking for a full-day, well-balanced experience that captures the essence of Tuscany—without feeling rushed—will find this tour hits the mark.

The Sum Up

This horseback ride in San Gimignano, combined with a flavorful Tuscan lunch and Chianti wine tasting, offers a well-rounded glimpse into Tuscany’s rural charm, historic towns, and culinary richness. The small-group format, expert guides, and diverse activities create a memorable, authentic experience that balances adventure with relaxation.

If you’re after an active, delicious, and culturally immersive day in Tuscany, this tour is a strong contender. It’s perfect for those who want to see Italy from a different perspective — on horseback, wandering medieval streets, and savoring regional wines.

While weather can impact the day, most reviews suggest that with some planning, this is a value-packed experience that’s worth every euro. For travelers craving more than just sightseeing, but rather an authentic taste of Tuscan life, this tour makes a fantastic choice.

Frequently Asked Questions

Is transportation provided?
Yes, roundtrip transportation from Florence is included in a comfortable, AC-equipped 8-seater minivan.

Can kids participate?
Children older than 6 years and taller than 1.10 meters are allowed to ride the horses, making it family-friendly for older kids.

What should I wear?
Comfortable clothing suitable for outdoor activities and sturdy shoes are recommended, especially for the horseback riding and town exploration.

Is the tour suitable for non-riders?
Absolutely. If you prefer not to ride, you can opt to substitute a farm tour instead of the horseback riding.

What’s included in the price?
The price covers transportation, the horseback ride, guided visits, lunch with wine pairing, tastings, and a guided tour of San Gimignano.

Are vegetarian, vegan, or gluten-free meals available?
Yes, special dietary requests can be accommodated upon prior notice.

What happens if the weather is bad?
The tour requires good weather. If canceled due to rain or poor conditions, you’ll be offered a different date or a full refund.

This tour offers a genuine slice of Tuscany, blending outdoor adventure with regional culture and cuisine. For those looking to combine activity with indulgence and history, it’s a memorable way to spend a day outside Florence.