
” ‘Andiamo,’ let’s go, the sound comes out at a gallop.” Frances Mayes
Imagine riding horses under cypress shadows that fall in wide bands across a sunlit pathway that meander over the hillsides of Tuscany. Endless blue skies blown clean of clouds frame medieval villages and vineyards. Birdsong and breezes gently caress your senses and nature is suddenly all around you.
Have any of you, like myself, ever dreamed of riding from castle to castle on horseback? Recently, I have fallen in love with a similar idea. Riding from winery to winery on horseback. But the very best is to combine the two of them together and ride to castles and wineries on horseback! And what better place to journey through than Tuscany.
Tuscany is a primeval land full of history, legends, and ancient peoples. Pathways wind through meadows and forests that pilgrims walked many centuries ago. Olive groves, vineyards and cypress trees embellish the landscape in the most striking tones, giving a balance of beauty that soothes and refreshes the soul.
Chianti is a region in Tuscany located between Florence and Siena. Steeped in ancient history, the land has grown wealthy from wine. Today the vineyards produce an excellent quality. This was not always the case. Many of us remember the cheap Chianti encased in a wicker bottom with a candle sticking out of it, displayed in Italian restaurants years ago. However, the wine has changed with time and today has become some of the best in the world. Classico is a term used which means that the wine is grown in the oldest zone of origin. The map below shows the area.

Chianti wine was first mentioned in a document from 1398. The above outlined Chianti area boundaries have been fixed since 1932 and have stayed the same. But not all are Chianti Classico. Divided into 8 sub-zones, each one produces its own Chianti wine. As you ride through the region, you will find many farms and wineries along the road offering wine tasting.
There is no better way to experience the sights, smells, and tastes of Tuscany than on horseback. Enjoy a day under the Tuscan sun and experience the ambience close up and personal. Below I have listed a few recommended riding experiences that offer wonderful horses that anyone can ride. Click on the titles to open the websites. I have provided a brief description after each title.
After riding for two hours through the Chianti hillsides, you will return to the stables and enjoy a robust Tuscan lunch of salamis, cheeses, meats, fresh vegetables and wines from the same vineyards you just rode through.
Beginning with a one hour ride through vineyards, olive groves, and medieval villages to a 17th century Villa’s estate, you will be taken on a guided tour of the ancient cellar. The unique process of making olive oil and wine will be discussed, followed by tasting the olive oil and several wines. A Tuscan lunch, consisting of bruschetta and pasta, or dinner for the pm ride, will be served afterward.
Seven Castles of Chianti on Horseback
For those who are up for a week-long excursion, this is the one. This rides takes you on a wide loop through the Chianti Classico wine region north of Siena.
Heads up, heels down and enjoy the ride!