Spend a full day on horseback through the Chianti hills, crossing oak woodlands and the Arbia river before arriving at the thousand-year-old Dievole estate for a guided wine tasting and rustic lunch. This ride blends easy equestrian terrain with cultural insight into Tuscan winemaking.
More ways to explore the area's outdoor wonders
You saddle up on a cool Tuscan morning, the horse shifting beneath you as cypress-lined lanes open onto a widening view of soft, cultivated hills. The trail climbs from Cignano hill, drops toward the Arbia river, and threads through oak and holm oak where birds call and the undergrowth rustles like a companion urging you on.
Difficulty
easy
Duration
8–10 hours (full day)
Fitness Level
Suitable for beginners and regular riders; basic balance and the ability to mount/dismount independently are helpful.
Wildlife
History
Dievole estate's recorded origin dates to 1090; the area has long combined hill farming, viticulture and transhumant routes that shaped local tracks.
Conservation
Stay on marked trails and pack out waste; many estates practice sustainable viticulture—support them by following guidelines and buying local wine.
Reserve your spot on the Wine and Horses today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Book with rider details
Provide your height, weight and riding experience when booking so guides can match tack and choose the right mount.
Footwear matters
Sturdy ankle-support boots with a small heel help keep your foot in the stirrup and protect against brush on singletrack sections.
Hydrate and pace
Carry a refillable water bottle and sip regularly—the sun on open hills can be stronger than it feels in the saddle.
Respect vineyards
Stay on designated trails and avoid stepping into vine rows; these are working farms and crops can be fragile.
Riding helmet
Many operators provide helmets, but bringing a well-fitting helmet increases comfort and safety.
Ankle-support boots
Closed-toe boots with a small heel protect feet and help keep your foot secure in the stirrup.
Weatherproof layers
Light waterproof and windproof layers handle morning chill and sudden showers in shoulder seasons.
spring
Refillable water bottle
Staying hydrated on a full-day ride through sun-exposed hills prevents fatigue and headaches.
summer