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Experience the scenic Tuscan hills on horseback with this guided tour from Siena, featuring gentle horses, beautiful landscapes, and expert guidance for all levels.
The Tuscan Chianti Hills Horseback Riding Tour offers a charming way to explore the rolling landscapes of Tuscany just outside Siena. At a cost of $86.73 per person, this 1.5-hour guided experience provides a relaxed ride suitable for novice and intermediate riders. The tour departs from Strada del Pian del Lago in Siena, and includes a local guide, helmet use, and the ride itself, with no additional costs for equipment. While the location is somewhat remote, the tranquil setting combined with well-trained horses makes it an engaging outing for those seeking a scenic escape from the city.
Most bookings are made about 22 days in advance, reflecting its popularity among travelers looking for an authentic Tuscan experience. The tour is especially appealing for those who appreciate calm, gentle horses and stunning countryside views, with some reviews highlighting how the experience can serve as a peaceful retreat. However, potential participants should be aware that transport to the meeting point is not included, and the location might require a taxi or private car, which can add to the cost.


The tour begins in central Siena, where travelers hop into a comfortable minivan to reach the stables. After a brief safety talk and a quick practice riding session in the arena, riders are introduced to their gentle horses. The horses are chosen to match each rider’s confidence level, ensuring everyone has a comfortable start. The guides are experienced, often highlighted for their friendly attitude and local knowledge.
Once on horseback, the journey takes you along horseback riding trails used by ancient peoples, with the scenery shifting between lush forests, rolling vineyards, and terracotta-roofed villages. The views of villa-crowned hills and medieval towns like Monteriggioni are frequent sights, providing plenty of photo opportunities. For those with more confidence, the guide offers opportunities to trot or canter on certain stretches, adding a bit of excitement for more experienced riders.
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The departure point is located at Strada del Pian del Lago, a bit outside the main historic center of Siena. The transport to the stables involves a short minivan ride, after which the focus shifts entirely to the ride itself. The group size is typically limited to 15 participants, allowing for more personal attention from the guides.
The ride usually begins at a leisurely pace, following trails that wind through countryside and rustic villages. These paths are often used by pilgrims on the Via Francigena, connecting historical routes with spectacular scenery. The hilly terrain offers both gentle inclines and flat stretches, making it manageable for most riders, especially those with basic riding skills.
The horses are described as calm, obedient, and well-trained, making them suitable for beginners and intermediate riders alike. Several reviews highlight their gentle temperament and reliable behavior, which helps riders enjoy the experience without unnecessary concern. The guides are praised for their friendly demeanor and local insights, often sharing stories about the area’s history and landscape while leading the group.
Although most guests find the horses suitable, some comments mention that horses for learners are underweight or less groomed at certain times, so it’s wise to be prepared for a more rustic experience. The guides do their best to match horses with rider experience, ensuring safety and enjoyment.

During the ride, visitors pass through olive groves, vineyards, and forests, with many trails offering dappled shade. The views of Siena’s hills and nearby towns like Monteriggioni are especially striking, giving a true sense of Tuscany’s landscape. Some trails are zigzagging, allowing riders to admire the patchwork of farmland and villa-crowned hills from different angles.
One of the notable features of this tour is its inclusion of ancient trails historically used by pilgrims, adding a touch of historical significance to the scenery. Riders can expect a slow walk, with opportunities to increase pace if they wish, making it a relaxing ride for most.

The meeting point requires arriving by taxi or private car, as there is no included pickup. The location is near public transportation, but guests should plan ahead to avoid delays. The minimum age to participate is 14 years, and participants should wear long-sleeved tops, leggings or jodhpurs, and closed-toe shoes with non-slip soles.
The tour operates with a minimum of 2 participants and can accommodate up to 15 riders. The overall pace is generally slow to moderate, with more advanced riders having the chance to trot or canter, depending on conditions and the guide’s assessment.

Some reviews mention logistical issues like late starts or disorganized arrivals, often related to transportation or communication. One guest noted that the location felt remote, and getting there required extra effort and expense. The horses’ condition and the size of the group have also been points of criticism in some feedback, especially when groups include beginners or inexperienced riders.
However, many guests highlight the friendly guides, beautiful scenery, and calm horses as major positives. The experience excels for those seeking a relaxed, scenic ride rather than a high-adrenaline adventure.

This horseback riding experience is best suited for beginners and intermediate riders who enjoy calm horses and peaceful landscapes. It offers a relaxed pace with stunning views that make it ideal for photography and nature lovers. Participants should be prepared for remote locations and some logistical planning to reach the meeting point.
While advanced riders may find some stretches enjoyable, the emphasis is on scenic strolling rather than gallops or canters. Riders with limited mobility might find the terrain manageable, but should be comfortable mounting and dismounting independently.

The Tuscan Chianti Hills Horseback Riding Tour provides an authentic look at Tuscany’s countryside through a calm, guided ride. Its well-trained horses and friendly guides create a welcoming atmosphere, especially for less experienced riders. The spectacular scenery, including vineyards, olive groves, and medieval villages, makes this a memorable outdoor activity.
On the downside, the remote location and transport logistics may require extra planning, and some guests have noted disorganized arrivals or horses that don’t meet expectations. This tour offers a relaxing, scenic horseback ride suitable for families, couples, and solo travelers seeking a peaceful way to enjoy Tuscany’s landscape. It’s a worthwhile experience for those who appreciate nature, history, and gentle horses in a beautiful setting.
“I had the most wonderful time on this trail ride. I found myself alone in Siena and needed to find something to do. I am so thankful I found this e…”
Is transportation included with this tour?
No, transportation is not included. Guests must arrange their own taxi or private car to reach the meeting point at Strada del Pian del Lago.
What is the minimum age to participate?
Participants must be at least 14 years old to join this horseback riding experience.
Do I need prior riding experience?
No, the tour is mainly aimed at novice and intermediate riders, and horses are chosen based on rider ability. Basic riding commands are sufficient for most.
What should I wear for the ride?
Guests should wear a long-sleeved top, leggings or jodhpurs, and closed-toe shoes with non-slip soles for safety and comfort.
How long does the ride last?
The actual horseback riding time is approximately 1 hour and 30 minutes, including safety instructions and practice.
Are the horses suitable for beginners?
Yes, the calm, well-trained horses are suited for beginners and those with moderate riding confidence.
Can experienced riders participate?
Yes, more experienced riders have the option to trot or canter during stretches, provided conditions permit.
What should I do if I face logistical issues?
Because the location is remote, ensure you plan your transport carefully. Some reviews mention difficulty in finding the meeting point, so arrive with enough time.
Is this tour kid-friendly?
Yes, children aged 14 and over can participate, making it suitable for families with teenagers interested in horseback riding.
What is the cancellation policy?
You can cancel free of charge up to 24 hours in advance. Cancellations made less than 24 hours before the experience are not eligible for a refund.