Horse Riding the Chianti Trails in Tuscany, Italy

February 24, 2013

A horse riding guide from Castellare di Tonda describes her favorite trek, halfway between Florence and Siena in the heart of Tuscany.

written by Jess Morton
photos by Christiane Slawik and Nate Wade


The horses waited patiently while riders smeared sunblock over their arms and noses. The saddlebags were packed and secured, and I started to bridle each horse and call the respective rider over to mount up. Today’s group was big by Castellare di Tonda's standards. Nine riders, all from the north of England, chatted and laughed while one by one their horses were brought out.

We departed for a special trek during this Italy riding vacation via a hidden forest trail behind the stables. The horses that were left behind called to us from their boxes, and we took the sandy descent down into a shaded tunnel of Mediterranean trees.

italy horse riding vacations

The famous Tuscan countryside surrounding Castellare di Tonda in Italy.

Dust rose behind us as we rode down into the canyon. The horses were keen and strode out happily. Behind me, riders laughed and teased each other. These were all English riders, and the novelty of a western saddle and split reins made for affectionate references to John Wayne and various spaghetti westerns.

We crossed the creek at the bottom of the canyon and rode up the spiral trail to the Chianti vineyards of the neighboring property Castelfalfi. Here we leveled off and rode along red sand trails that offered a panoramic view of Tonda behind us. The Tonda village, with its medieval church spire and triangular architecture, looks like something straight out of a Grimm brother fairy tale.

italy horseback riding vacations

These Italy riding vacations traverse a variety of landscapes; shady Mediterranean forests, rolling golden grain fields, vineyards and olive groves.

We rode back into thick woods along a narrow trail that I had to re-open with my husband’s machete a few weeks ago. This part of the trail ride is more challenging than most, and the horses need to pick their way over a fallen log and pass through a thin section that only allows for one horse at a time.

We passed through and the trail opened up until we were at the top of the ridge. We rode along this ridge to another adjoining one take a couple of exhilarating canters through the vineyards. Long soft trails between the vines afforded us magnificent views of the countryside all around.

tuscany horse riding holidays

Castellare di Tonda has been producing wine for over 30 years. 

Finally, we arrived at the small medieval village of Castelfalfi. The fortified castle and aged stone buildings are thought to date back 1000 years. The castle is complete with turret, a small tower rising above and resting on one of the main towers, and a dark dungeon.

We dismounted, hitched the horses to some trees in a well maintained garden park, and began to take photos. The view from Castelfalfi is spectacular. The largest golf course in Tuscany lies to one side of the town, while the other side is surrounded by a dark green lake.

Castellare di Tonda

A group photo at one of the scenic stops along the trail ride.

We rode the horses down to this lake, past a wooden house that was used for filming a recent Pinocchio movie (it was the fairy's house). The wildflowers here are vibrant and color the landscape pops dramatically with swathes of red, pink and yellow as far as the eye can see. In the distance, solitary cyprus trees line the top of the rolling hills toward Peccioli.

As we departed the lake area, we allowed the horses various canters on the network of grassy trails through the game reserve before returning back to the stables along an old Roman cobbled road lined with tall pine trees. We passed lonely abandoned farmhouses–– proud and magnificent even in their ruined state.

tuscany horse riding vacations

Riders discover medieval castles and abandoned churches on horseback.

Finally on the last section of the trail, we encountered three fallow deer grazing in a field. They glanced at us hesitantly, and watched us for a moment as we troted past, before taking their exit and bounding into the forest below them.

On our return, the riders un-tacked their own horses and washed him down, giving them apples secretly taken from the breakfast table. The sun by this stage was hot, and riders splashed their faces with cool water.

italy horse riding holidays

Castellare di Tonda breeds and trains Quarter horses and Paint horses and offers Western riding in Italy.

After the horses were put away, everyone headed back to their farmhouse for lunch and a swim. We would meet again later in the afternoon for a twilight ride to the nearby village of Sughera. A different type of ride, this one would be along mountainous, wild alpine trails with views of a different kind-- views that run all the way to Volterra, the Etruscan city in the distance.

After saying goodbye, I pack my Border Collie in the car, and head home for the siesta break-- another typical morning riding the trails of Tuscany at Castellare di Tonda.


Learn more about riding vacations in Italy with Castellare di Tonda on their website. Check out Castellare di Tonda in the Equitrekking Vacation Guide to ranch and horseback riding vacations around the world.

Topics: castellare di tonda, italy equestrian vacations, italy horse holidays, italy horseback riding vacations, italy riding holiday, italy riding holidays, tuscany equestrian vacation, tuscany equestrian vacations, tuscany riding holiday, tuscany riding holidays, tuscany riding vacation, tuscany riding vacations