Horseback Riding with Wine Tour from Florence

Discover Tuscany’s Charm on Horseback with a Wine and Food Experience from Florence

If you’re looking for a day that combines scenic horseback riding, medieval towns, and tasting some of Italy’s finest wines, this tour offers a well-rounded taste of Tuscany. For around $220 per person, you’ll spend about 8 hours exploring the countryside, visiting San Gimignano—famous for its towers—and sipping local wines at a family-run winery. Led by personable guides like Lorenzo, who delight in sharing their love of the region, this experience is as much about genuine local flavor as it is about picturesque scenery.

What we love about this tour is the gentle horseback ride through vineyards and olive groves, which requires no prior riding experience—making it accessible for most. Plus, the small group size (max 8 participants) ensures a relaxed, personalized atmosphere, perfect for those who prefer intimate travel experiences. The included Tuscan lunch paired with a wine tasting adds significant value, giving you a chance to savor regional specialties and high-quality wines without the hassle of organizing it yourself.

A possible consideration is the weather dependency—since the day involves outdoor activities, poor weather could impact your experience or lead to a reschedule. Also, while the tour is generally praised for its value, some might find that the horseback riding views do not always match the idyllic photos, as one reviewer pointed out. Still, these minor hiccups don’t overshadow the overall quality and charm of the day.

This tour suits travelers eager to see Tuscany beyond Florence, especially those interested in history, scenery, and local wines. It’s perfect for small groups or couples wanting a more relaxed, personalized experience with authentic touches that make Tuscany special.

Key Points

• Accessible horseback riding through vineyards and olive groves — no experience needed.
• Visit San Gimignano, one of Italy’s most picturesque medieval towns with towers, piazzas, and sweet gelato.
• Enjoy a farm-to-table Tuscan lunch paired with guided wine tastings of famous regional wines.
• Small group size (up to 8 people) for a more personal experience.
• Breathtaking views from Piazzale Michelangelo to round off the day.
• Flexible cancellation policy: free up to 24 hours in advance.

A Detailed Look at the Tuscan Horseback & Wine Tour

This tour offers a rare chance to combine scenic horseback riding with cultural exploration and culinary delights. It’s designed to give you a taste of what makes Tuscany so beloved—its rolling landscapes, centuries-old towns, and world-class wines—without feeling rushed or crowded.

The Itinerary: A Day of Authentic Experiences

Start at San Gimignano with a Gentle Horseback Ride
Your adventure begins in the morning at a convenient meeting point in Florence, from where you’ll be transported to the countryside. Once there, your guide will match you with a suitable, well-trained horse—whether you’re a seasoned rider or a total novice. The two-hour horseback ride is designed to be relaxed and scenic. Expect to glide past vineyards and olive groves, with plenty of opportunities to admire the landscape without the adrenaline rush of a fast-paced ride.

Many reviews highlight how gentle the horses are, making it a perfect introduction for beginners or those who simply want to enjoy nature on horseback. As one traveler said, “The horses were very good trained,” which speaks to how the experience is crafted for comfort and safety.

Wander San Gimignano’s Medieval Streets
Next, you’ll explore this UNESCO World Heritage site, often called the medieval Manhattan thanks to its iconic towers. The town boasts narrow cobblestone streets, scenic piazzas, and historic buildings with origins stretching back to Etruscan and Roman times. It’s a favorite for many travelers, with its well-preserved architecture and charming ambiance.

A highlight for many is stopping by Dondoli Gelato, renowned as the world champion of gelato. One review raves: “A stop at Dondoli Gelato will make your taste buds happy!” It’s a delightful treat after wandering through the town’s scenic streets.

Wine and Lunch at a Tuscan Winery
The afternoon involves visiting a local winery for a farm-to-table Tuscan lunch, paired with guided tastings of some of Italy’s most famous wines, like Chianti. The tasting isn’t just about drinking; it’s educational, with guides explaining the magic of the Chianti region and how the wines are made. You’ll also sample high-quality extra virgin olive oil and regional specialties.

Several reviews praise the high quality of the wines and the delicious lunch, describing the experience as “fabulous” and “spectacular.” The value here is clear: you’re getting a farm-fresh meal combined with expert wine tastings, which could cost a lot more if you organized it yourself.

Cap the Day with Florence Views from Piazzale Michelangelo
After exploring and indulging, the tour concludes with a visit to Piazzale Michelangelo. From this famous vantage point, you can view the Florence skyline, including the Duomo and Ponte Vecchio, making it a fitting end to your Tuscan adventure.

The Experience: What Makes It Stand Out?

The small group size means you won’t be lost in a crowd, and guides like Lorenzo, Christian, and Daniel are praised for their knowledge, friendliness, and hospitality. As one reviewer stated, “Our guide Lorenzo was very nice,” adding that the day was “really a perfect day.”

The horseback riding component is a major draw, especially since many travelers have never ridden horses before but found the experience accessible and enjoyable. “No experience required,” as the itinerary notes, and many reviewers echo this, emphasizing how well it’s tailored for beginners.

The wine tasting and lunch at a family-run winery deepen your connection to the land and its traditions. With fabulous wines, a delicious meal, and friendly hosts, this segment captures the essence of Tuscany’s culinary culture.

The Logistics: What You Need to Know

Departure is at 9:00 am from Florence, with the tour lasting approximately 8 hours. The tour is limited to up to 8 participants, which keeps things cozy and personalized. The meeting point is easy to find, located on Via Curtatone in Florence, and transportation is included in the package, making logistics simple.

While the tour doesn’t include private pick-up and drop-off, it’s easy to reach the meeting point via public transport or a short taxi. The free cancellation policy up to 24 hours in advance adds flexibility, especially if weather turns sour.

The Real Experience: Authenticity and Value

Many travelers praise the authenticity of this tour. It’s less about glitz and more about genuine Tuscan life—horseback riding through vineyards, wandering an ancient town, tasting local wines, and enjoying regional cuisine. The small group setting ensures a relaxed environment, where guides can tailor the experience to the group’s interests.

The value is particularly notable when you consider what’s included: horseback riding, San Gimignano exploration, a farm-to-table lunch, wine tastings, and transport—all in one day. Several reviews mention how much they packed into the day, with descriptions like “we saw a lot” and “got so much done in one day,” highlighting the efficient and well-organized nature of the experience.

Who is This Tour Best For?

This experience appeals most to couples, small groups, or solo travelers looking for a blend of outdoor adventure, cultural exploration, and culinary delights. It’s ideal if you love beautiful scenery, good wine, and history but prefer a more intimate setting over large bus excursions. It suits those beginners or experienced riders alike because of the gentle horses and relaxed pace.

If you’re someone who wants to escape the crowds of Florence and see a more authentic side of Tuscany, this tour offers a perfect balance. It’s not just about ticking sights off a list, but about enjoying the land, flavors, and atmosphere.

FAQs

Is horseback riding suitable for beginners?
Absolutely. The horses are described as gentle and well-trained, and no riding experience is required. The ride is relaxed and scenic, designed for all comfort levels.

What is included in the price?
Your ticket covers the horseback ride, visit to San Gimignano, lunch with wine tasting, and transportation from Florence. The tour is limited to small groups for a more personalized experience.

How long is the horseback ride?
The horseback riding segment lasts approximately 1 hour but is part of an overall 8-hour experience, including visits, meals, and sightseeing.

Can I cancel if the weather is poor?
Yes, cancellations are free up to 24 hours before the tour, and if severe weather causes cancellation, you’ll be offered a different date or a full refund.

What’s the worst that could happen?
Some reviews mention that views may not always match promotional photos, and weather may impact the outdoor activities. But guides are praised for their friendliness and professionalism.

Is transportation from Florence included?
Transport is included in the tour price, so you won’t need to organize your own ride to the meeting point.

What are the group size and tour duration?
The tour is limited to 8 participants and lasts about 8 hours, providing a leisurely pace with ample time at each stop.

Final Thoughts

For those craving a day of gentle adventure combined with authentic Tuscan flavors, this horseback riding and wine tour hits the mark. You’ll appreciate how well-organized it is, the friendly guides, and the chance to see Tuscany’s countryside, medieval towns, and enjoy regional wines without the hassle of planning everything yourself.

It’s a particularly good choice for small groups or couples, seeking a relaxed, intimate experience that balances outdoor activity with cultural and culinary immersion. While the weather can influence the day, the overall vibe, authentic stops, and knowledgeable guides make it a worthwhile investment.

If you’re after a memorable, well-rounded day that captures the essence of Tuscany—this tour is a charming way to do it.