Discovering Tuscany on horseback is one of the most immersive ways to experience the iconic Chianti landscape. Framing the rolling hills, ancient vineyards, and olive groves, the medieval skyline of San Gimignano provides a breathtaking backdrop for an equestrian adventure.
Whether you are looking for a quick trail ride through Tuscan nature, an all-inclusive day trip from Florence with wine tastings, or a horseback excursion paired with an authentic farm-to-table lunch, this guide covers the top-rated tours available, complete with pricing, inclusions, and flexible booking options.
Comparing the Best San Gimignano Horseback Riding Tours
| Tour Experience | Best For | Duration | Price (per person) | Free Cancellation | Key Features |
| 1-Hour Nature Trail Ride | Quick adventure / Beginners | 1 hour | From €74 | Up to 24 hrs prior | Guided ride, safety gear included, small groups |
| Small Group Tour: Horseback, Town & Winery | All-inclusive day trip / Wine lovers | 7 hours | From €200 | Up to 24 hrs prior | Hotel pickup from Florence, gelateria visit, winery lunch & tasting |
| Trail Ride & Farmhouse Meal | Foodies & couples | 3 hours | From €99 | Up to 24 hrs prior | 1-hour ride + authentic Tuscan lunch or dinner in an agriturismo |
1. San Gimignano: Horseback Riding Walk in Nature
If you want a straightforward, refreshing escape into nature, this one-hour guided horseback trail ride offers an ideal introduction to the Tuscan countryside.
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Target Audience: Perfect for beginners, couples, or travelers with a busy itinerary who want a high-quality equestrian experience without committing a full day.
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Duration: 1 hour.
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Price: From €74 per person.
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Key Inclusions: Professional equestrian guide, horse and riding gear, mandatory safety helmet.
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Requirements: Participants must be at least 14 years old. Long pants and closed-toe shoes are required.
Starting in the scenic hills surrounding San Gimignano, you will be matched with a gentle horse suited to your experience level. Accompanied by expert safety guides, the route wind through vineyards, olive orchards, and tranquil woodland trails. Morning and afternoon departure slots provide maximum flexibility for your travel schedule.
2. Tuscany: Horseback Riding, San Gimignano & Winery Lunch (Small Group)
For travelers seeking a complete Tuscan cultural and culinary day trip, this top-rated 7-hour tour combines outdoor adventure, medieval sightseeing, and fine dining.
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Target Audience: Travelers staying in Florence or nearby who want a seamless, all-inclusive day tour with transportation provided.
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Duration: 7 hours.
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Price: From €200 per person.
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Key Inclusions: Round-trip transfer in an air-conditioned 8-seater minivan, 1-hour horseback ride, guided visit to San Gimignano, gelato stop at world-champion Dondoli, and a 3-course winery lunch with guided wine and olive oil tastings.
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Requirements: Suitable for beginners. Riders must be at least 8 years old and at least 1.10 meters (3 ft 7 in) tall.
Your journey begins with a comfortable minivan ride into the heart of Chianti. Following a safety briefing and a peaceful 1-hour ride through vineyard-draped hills, you’ll head to the UNESCO World Heritage town of San Gimignano. Enjoy guided free time to explore the iconic medieval towers and sample award-winning gelato. The experience concludes at an authentic local estate for a classic Tuscan lunch paired with Chianti Classico wines, extra virgin olive oils, and aged balsamic vinegar.
3. San Gimignano: Horse Riding in Nature with Farmhouse Lunch or Dinner
Combine scenic trail riding with authentic Tuscan gastronomy in this popular 3-hour experience set in an picturesque agriturismo (farmstay).
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Target Audience: Food enthusiasts, small groups, and travelers wanting an immersive farm-to-table dining experience right after their ride.
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Duration: 3 hours.
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Price: From €99 per person.
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Key Inclusions: Professional riding guide, full equipment, safety helmet, and a complete traditional lunch (1:00 PM) or dinner (8:00 PM) at a rustic countryside farmhouse.
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Requirements: Minimum age of 14 years; maximum weight limit of 100 kg (220 lbs).
After spending an hour riding through scenic country paths near San Gimignano, relax at an agriturismo nestled in the hills. Indulge in home-cooked Tuscan specialties made with local ingredients, traditional pasta dishes, and local wines. Choosing between a sunny lunch or an evening dinner under the stars makes this one of the most memorable romantic activities in the area.
Frequently Asked Questions
Do I need prior horseback riding experience?
No. All featured tours cater to beginners and first-time riders. Before embarking on the trail, professional guides provide a comprehensive safety briefing and basic instructions on handling your horse.
What should I wear for horseback riding in Tuscany?
Always wear comfortable long pants (such as jeans or leggings) to protect your legs from saddle friction, alongside sturdy closed-toe shoes or boots. Avoid sandals, shorts, or loose skirts. Safety helmets are provided on-site and are mandatory.
Why book via GetYourGuide?
Booking online ensures clear pricing, instant mobile ticket confirmation, guaranteed spots during peak season, and maximum peace of mind with 24-hour free cancellation and flexible payment options.
Complete Your Tuscan Escape with Tuscan Mansions
After an unforgettable day horseback riding across the hills of San Gimignano, unwind in total luxury and comfort. Tuscan Mansions offers an exclusive portfolio of private luxury villas, restored farmhouses, and historic estates across the region. Featuring private swimming pools, panoramic hill views, and bespoke concierge services, these properties provide the ultimate sanctuary for your holiday in Tuscany.
