THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Spend a day riding gentle horses through Chianti vineyards, explore San Gimignano’s medieval towers, and cap it with a farmhouse lunch and guided wine tasting. This small-group tour blends easy riding with cultural stops and local flavors.
Spend a day riding gentle horses through Chianti vineyards, explore San Gimignano’s medieval towers, and cap it with a farmhouse lunch and guided wine tasting. This small-group tour blends easy riding with cultural stops and local flavors.
A slow morning light falls across gravel tracks as riders mount gentle geldings and push off from a farmhouse drive. The horses know the rhythm of the fields; they step through vineyard rows and olive groves, nudging riders toward low ridgelines where the Tuscan plain opens into towered medieval silhouettes.
Verified experiences and guided adventures in the surrounding area.
Operated by Fun In Tuscany · San Gimignano, Tuscany
A slow morning light falls across gravel tracks as riders mount gentle geldings and push off from a farmhouse drive. The horses know the rhythm of the fields; they step through vineyard rows and olive groves, nudging riders toward low ridgelines where the Tuscan plain opens into towered medieval silhouettes.
The route threads a living landscape shaped by Etruscan terraces and medieval commerce—San Gimignano's skyline of stone towers grew from rivalry and trade, while the Chianti hills carry centuries of vine cultivation that monasteries and local families refined into modern labels. The limestone-soil slopes and clay pockets give wines their structure; the same terrain makes for soft, rolling tracks with short, manageable climbs that suit first-time riders.
On tour: a small-group transfer from Florence, a fitting-to-rider horse, roughly one hour in the saddle across farm lanes and vineyard tracks (about 4–6 km of riding), a 90-minute walk through San Gimignano’s medieval streets, then a farmhouse lunch with guided wine tasting of Chianti wines and extra-virgin olive oil. No prior riding experience is required; guides handle horsematching and basic instruction.
Practical edge: wear sturdy closed-toe shoes or paddock boots, bring layered sun protection, and pack a small daypack with water and a light rain shell—weather can change quickly on exposed ridgelines. The full itinerary runs about eight hours; cancellation is allowed up to 24 hours before departure. Expect a mix of cultural sightseeing and mellow riding that pairs motion with tasting—ideal for travelers who want active hours on horseback followed by long-table local flavors.
No—guides match riders to well-trained, gentle horses and provide basic instruction so beginners can participate safely.
The tour includes about one hour of actual riding across farm tracks and vineyards, with additional time for transfers, San Gimignano, and lunch (total ~8 hours).
Yes—lunch at a farmhouse with a guided tasting of local Chianti wines and extra-virgin olive oil is included in the price.
You may note dietary needs during booking; however, the tour is not recommended for travelers with serious back, heart conditions, or pregnancy—notify the operator in advance for accommodations.
Fun In Tuscany operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
A slow morning light falls across gravel tracks as riders mount gentle geldings and push off from a farmhouse drive. The horses know the rhythm of the fields; they step through vineyard rows and olive groves, nudging riders toward low ridgelines where the Tuscan plain opens into towered medieval silhouettes.
A slow morning light falls across gravel tracks as riders mount gentle geldings and push off from a farmhouse drive. The horses know the rhythm of the fields; they step through vineyard rows and olive groves, nudging riders toward low ridgelines where the Tuscan plain opens into towered medieval silhouettes.
The route threads a living landscape shaped by Etruscan terraces and medieval commerce—San Gimignano's skyline of stone towers grew from rivalry and trade, while the Chianti hills carry centuries of vine cultivation that monasteries and local families refined into modern labels. The limestone-soil slopes and clay pockets give wines their structure; the same terrain makes for soft, rolling tracks with short, manageable climbs that suit first-time riders.
On tour: a small-group transfer from Florence, a fitting-to-rider horse, roughly one hour in the saddle across farm lanes and vineyard tracks (about 4–6 km of riding), a 90-minute walk through San Gimignano’s medieval streets, then a farmhouse lunch with guided wine tasting of Chianti wines and extra-virgin olive oil. No prior riding experience is required; guides handle horsematching and basic instruction.
Practical edge: wear sturdy closed-toe shoes or paddock boots, bring layered sun protection, and pack a small daypack with water and a light rain shell—weather can change quickly on exposed ridgelines. The full itinerary runs about eight hours; cancellation is allowed up to 24 hours before departure. Expect a mix of cultural sightseeing and mellow riding that pairs motion with tasting—ideal for travelers who want active hours on horseback followed by long-table local flavors.