Small-Group Tuscany Horseback Riding and Winery Tour with Lunch and Wine Tasting
Ride through Chianti vineyards, savour a traditional Tuscan meal, and explore a UNESCO medieval town in one unforgettable day.
This Tuscany horseback riding and winery tour takes small groups through the rolling hills of the Chianti region, combining a guided equestrian ride with a sit-down lunch, five-wine tasting, and a free-roaming visit to San Gimignano. No prior riding experience is required, making it accessible to first-timers and seasoned travellers alike.
The day begins with a scenic drive through Chianti's vine-covered countryside before reaching a peaceful horse riding school nestled among the Tuscan hills. Experienced staff introduce guests to the horses and lead an easy, one-hour ride through vineyards, native woodlands, and olive groves at a pace suited to all confidence levels.
The tour then moves to a family-run winery in the heart of Chianti, where guests sit down to a generous spread of local cheeses, salami, bruschetta, and extra virgin olive oil, all paired with five regional wines including classic Chianti. The afternoon closes with over an hour of free time in San Gimignano, the tower-studded medieval town recognised as a UNESCO World Heritage Site.
Tour Highlights
Guided ride through Chianti vineyards, olive groves, and native woodlands with no experience needed.
Traditional Tuscan lunch at a local winery featuring cheeses, salami, bruschetta, and five wines.
Tasting of extra virgin olive oils and balsamic vinegar produced in the Chianti region.
Over an hour of free time to explore the medieval towers and cobblestone streets of San Gimignano.
Small-group format ensures personal attention from guides and winery hosts throughout the day.
Multiple departure points available, including Florence and Barberino Tavarnelle, for added convenience.
Itinerary
Meet your tour leader at the designated departure point and set off into the Chianti hills. En route, your guide shares stories and background about the region's history, villages, and winemaking traditions.
Arrive at a tranquil riding school surrounded by the Tuscan countryside. The experienced team introduces guests to the horses and provides a brief orientation before the ride begins.
Ride at a gentle pace through vineyards, olive groves, and native woodlands, with sweeping views of the surrounding hills. No prior equestrian experience is necessary, and staff accompany the group throughout.
Head to a local Chianti winery for a traditional Tuscan meal paired with five wines, plus a tasting of extra virgin olive oils and balsamic vinegar. The setting is authentic and relaxed, giving guests time to enjoy the flavours at their own pace.
Spend over an hour exploring the medieval town of San Gimignano independently. Visit the Collegiata, climb Torre Grossa, browse artisan shops, or simply wander the historic piazzas of this UNESCO World Heritage Site.
After leaving San Gimignano, the group is transferred back to the original meeting point. Guests departing from Florence arrive back by early evening.
What Is Included
Included
- Guided horseback ride of approximately one hour
- Traditional Tuscan lunch at a local winery
- Tasting of five Chianti wines
- Tasting of extra virgin olive oils and balsamic vinegar
- Visit to San Gimignano with free exploration time
- Transportation throughout the tour
- Professional English-speaking tour guide
Not Included
- Hotel pick-up and drop-off
- Personal travel insurance
- Gratuities for guides and winery staff
- Additional food or beverages beyond the included meal
- Entrance fees to monuments in San Gimignano
Important Information
Reserve Your Spot in Chianti
Places on this small-group tour are limited. Secure your spot to experience horseback riding, authentic Tuscan wine, and the medieval streets of San Gimignano in a single day.
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