Saddle up for a gentle 90-minute ride through the Chianti hills—vineyards, olive groves, and medieval lanes reveal Tuscany’s history from the horse’s back. Ideal for novice and intermediate riders seeking scenic, small-group exploration.
Saddle up for a gentle 90-minute ride through the Chianti hills—vineyards, olive groves, and medieval lanes reveal Tuscany’s history from the horse’s back. Ideal for novice and intermediate riders seeking scenic, small-group exploration.
You climb into the saddle as morning light pushes across low, vine-stitched ridgelines and the horses step out onto a dirt track that smells faintly of olive oil and warm earth. The breeze moves through gnarled olive limbs and rows of grapevines, and the steady rhythm of hooves sets a cadence for taking in those wide, cultivated views that define Chianti.
Verified experiences and guided adventures in the surrounding area.
Operated by myTour in Italy · Siena, Tuscany
You climb into the saddle as morning light pushes across low, vine-stitched ridgelines and the horses step out onto a dirt track that smells faintly of olive oil and warm earth. The breeze moves through gnarled olive limbs and rows of grapevines, and the steady rhythm of hooves sets a cadence for taking in those wide, cultivated views that define Chianti.
This route threads the living history of Tuscany — medieval farmsteads, stone walls, and fields that reflect centuries of agrarian practice. Geology here is gentle: clay and limestone slopes carved into rounded hillocks that guide the trail and shape drainage, vineyards, and scrub oak. Culturally, you’re riding through land once contested by hill towns; Siena’s horses and festivals still recall that equine heritage.
Expect a relaxed, small-group pace aimed at novice and intermediate riders. The tack and helmets are provided, and guides will cover stable routines, mounting, and basic cues before you head out. The experience emphasizes quiet travel: staying on designated tracks preserves vines and prevents erosion, and your guide will point out lesser-known farm lanes and panoramic pullouts for photos.
Practical notes: wear long sleeves, closed-toe shoes with a low heel, and bring water. Timing rides for morning or late afternoon avoids the heat and yields better light for views. If you have back or heart issues, or are pregnant, this activity is not recommended. For most travelers comfortable mounting and dismounting unassisted, the ride offers a memorable way to encounter the Chianti hills without needing advanced riding skills.
moderate.
1.5 hours (90 minutes).
Suitable for people with basic mobility and no serious spinal or cardiovascular conditions; you should be able to mount and dismount unassisted and walk at a steady pace.
No — the tour welcomes novice and intermediate riders who can mount and dismount unassisted and follow basic rein cues; guides provide a stable briefing before departure.
Yes — helmets are provided and use is required for safety during the ride.
Minimum age is 14 years old; younger riders are typically not permitted due to safety and equipment sizing.
Pickup and dropoff are available if selected at booking; otherwise, public transportation options and central meeting points near Siena are common.
The Chianti hills have been shaped by centuries of mixed agriculture and the rivalry between Siena and Florence; many tracks follow historic boundaries and farm access roads.
Staying on marked trails and respecting cultivated land is essential; local stables emphasize low-impact riding to protect vineyards and reduce erosion.
myTour in Italy operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.




You climb into the saddle as morning light pushes across low, vine-stitched ridgelines and the horses step out onto a dirt track that smells faintly of olive oil and warm earth. The breeze moves through gnarled olive limbs and rows of grapevines, and the steady rhythm of hooves sets a cadence for taking in those wide, cultivated views that define Chianti.
You climb into the saddle as morning light pushes across low, vine-stitched ridgelines and the horses step out onto a dirt track that smells faintly of olive oil and warm earth. The breeze moves through gnarled olive limbs and rows of grapevines, and the steady rhythm of hooves sets a cadence for taking in those wide, cultivated views that define Chianti.
This route threads the living history of Tuscany — medieval farmsteads, stone walls, and fields that reflect centuries of agrarian practice. Geology here is gentle: clay and limestone slopes carved into rounded hillocks that guide the trail and shape drainage, vineyards, and scrub oak. Culturally, you’re riding through land once contested by hill towns; Siena’s horses and festivals still recall that equine heritage.
Expect a relaxed, small-group pace aimed at novice and intermediate riders. The tack and helmets are provided, and guides will cover stable routines, mounting, and basic cues before you head out. The experience emphasizes quiet travel: staying on designated tracks preserves vines and prevents erosion, and your guide will point out lesser-known farm lanes and panoramic pullouts for photos.
Practical notes: wear long sleeves, closed-toe shoes with a low heel, and bring water. Timing rides for morning or late afternoon avoids the heat and yields better light for views. If you have back or heart issues, or are pregnant, this activity is not recommended. For most travelers comfortable mounting and dismounting unassisted, the ride offers a memorable way to encounter the Chianti hills without needing advanced riding skills.