Chianti Hills Trail

7 Days | From £1783pp

Italy ( Best airport: Florence or Pisa)

This riding holiday in Chianti offers a unique way to explore the stunning Tuscan countryside, with its rolling hills, vineyards, olive groves, and charming medieval villages. As you ride through the picturesque landscape, you’ll pass by historic castles and abbeys, often with stops to enjoy the region’s renowned wine and cuisine. The small group size and knowledgeable owner guide ensure a personal experience, while the willing and responsive horses are the perfect partner to discover this enchanting part of Tuscany. A landscape of rolling hills covered in vineyards, ancient stone farmhouses, and winding country roads, this region has inspired poets, artists, and travellers for generations.

The Riding

The riding on this trail is relaxed, allowing you to connect with the stunning landscape in a way that’s different from other forms of travel. The terrain is varied, with gentle trails through vineyards, olive groves, and forested paths, as well as some more challenging areas with rolling hills and scenic viewpoints. Most of the rides are at a leisurely pace, allowing you to soak in the views, but there are opportunities for trotting or cantering where the terrain allows.

Along the way, you’ll stop at local wineries, where you can enjoy a break with a taste of local food andlocally produced wine. This trail offers an intimate way to explore Chianti, allowing you to see parts of the region that are otherwise inaccessible and to experience its beauty from a slower, more grounded perspective.

Much of the riding takes place on the Via Francigena, a 1800km ancient pilgrimage route that stretches across Europe, connecting Canterbury in England to Rome in Italy. You’ll pass through a variety of landscapes, including rolling hills, vineyards, forests, and small Italian villages. This stretch of the Via Francigena offers scenic views, historical landmarks, and cultural heritage, making it a popular route for those looking to combine nature, history, and great riding. The gaits are walk, trot and canter.

Level of Riding and Fitness

This trail is for intermediate riders upwards. You must be confident and in control riding outside an arena with a reasonable level of current riding fitness is required as you’ll be spending 4-5 hours in the saddle each day.

Guides and Group Size

Sergio, the owner of SA Ranch is your host for this holiday and will be your guide. Incredibly knowledgeable about the region’s history, he has been guiding trips through Tuscany for many years.

The group size is 2-6 riders and the maximum weight is 90 kilos.

Any questions?

The Horses

The horses at this destination are all very well cared for and there are a variety of different breeds; beautiful Quarter Horses, English Thoroughbreds, Arabian, Anglo-arab and Sicilian native breeds. The horses are responsive and surefooted and have all been trained by your guide and owner, Sergio.

Tack and Riding Equipment

There are both English and Western saddles available at this ranch.

Accommodation and Dining

You’ll be staying at the Agriturismo La Selva, an ancient and typical Tuscan farmhouse. La Selva offers welcoming and comfortable rooms and apartments, all with private bathrooms and fully furnished. After returning from a day of riding on horseback, there is no better way to relax than a dip in the on site outdoor swimming pool or kick back in the serene garden with a book.

This is a fully inclusive holiday with all meals provided. Dinners are at La Selva and lunches on the trail are usually at local vineyards. You’ll enjoy delicious Italian cuisine and have the chance to taste the local wines.

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Gallery

Itinerary

Day 1 Transfer from the airport to La Selva, your base for the week. Check-in and meet your fellow riders and guide over a delicious dinner with plenty of local wine.

Day 2 After breakfast you'll meet the horses and set off on the trail at 9.30. The first part of the route crosses the Pian del Lago, where until the mid-18th century there was a lake called Verano. This stretch of the Via Francigena will lead you to two ancient and well preserved castles built in the 13th century. Stop for a leisurely lunch before continuing on the Via Francigena, we pass through Abbadia Isola. “Abbadia” stands for abbey, the church being a Cistercian foundation, while “Isola” reminds us of the fact that it originally stood on the marshy Lake Verano. After passing Castel Pietraio we reach the horse stopping point of this first day.

Day 3 The Via Francigena will lead us, in the territory of Castellina in Chianti, to Villa Trasqua whose first records date back to the year 1001. Since then, the link between this farm and the territory has never been broken, continuing the production of Sangiovese and Chianti wines. This vineyard is 100% organic, and the wines produced will accompany today's lunch. Your journey continues along the vineyards of this part of the Sienese Chianti, crossing oak and holm woods, to reach the horse rest point.

Day 4 Today’s route will be on the hills of the Chianti Senese north of Siena. A rural landscape with woods, vineyards, centuries-old olive trees and sown fields. This will lead us to the Monaciano estate, dating back to the 18th century. After lunch, which will be accompanied by the wines produced on this estate, we set off again to reach the horse stopping point in Mociano. This location is important for the people of Siena because the selection and training activities for the horses of the Palio di Siena (a unique, annual, bareback horse race) are carried out here.

Day 5 Today from Chianti we move to the Crete Senesi, south-east of Siena. The name “Crete” derives from the clay present in the soil formed between 2.5 and 4.5 million years ago this entire area was covered by the sea. The landscape, depending on the seasons, can have a grey-blue colour, almost lunar or green, with gently rolling hills, oaks, cypresses, and isolated farms. After lunch, you'll explore the territory of San Rocco a Pilli, an area already inhabited in Etruscan and Roman times, before reaching the horse rest point in Rinidia.

Day 6 Today is the final riding day and to return to the equestrian centre you'll travel along part of the Via Francigena on the Sienese Montagnola. Having crossed Ponte allo Spino, an early medieval village, the paths will lead us to the Villa Cetinale built in 1676, to the Romitorio di Cetinale, an eighteenth-century religious building and to the Parish Church of Pernina, a church whose first records date back to 1078. After lunch the route continues on the Montagnola Senese, until reaching the Hermitage of San Leonardo al Lago which dates back to the year 1112. The Via Francigena will lead us to the equestrian centre where it is time to say goodbye to your lovely horses before enjoying a final dinner.

Day 7 Departure after breakfast either to the Siena train station or Pisa airport.