THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Spend a private day driving through Chianti’s sun-baked hills to San Gimignano and Siena, with vineyard tours and a light winery lunch. This curated route mixes medieval streets, geological terroir and hands-on wine tasting for a practical and picturesque Tuscan experience.
Spend a private day driving through Chianti’s sun-baked hills to San Gimignano and Siena, with vineyard tours and a light winery lunch. This curated route mixes medieval streets, geological terroir and hands-on wine tasting for a practical and picturesque Tuscan experience.
Book with Events in Italy
Book directly with Events in Italy for the best rates and real-time scheduling.
Reserve NowVerified experiences and guided adventures in the surrounding area.
Operated by Events in Italy · Florence, Tuscany
Morning light slides across the cypress-lined road as a private van departs Florence, the Chianti hills leaning in like attentive hosts. Vine rows march up sun-warmed slopes, and medieval towers of San Gimignano puncture the sky—landmarks that have watched this landscape for centuries.
easy.
8–9 hours.
Suitable for most fitness levels; involves short walks on uneven surfaces and stairs.
Most departures are from Florence hotels; confirm pickup point when booking.
Yes—tastings at a historical villa and vineyard plus a light lunch are included.
The tour is family-friendly but infants must sit on laps and tastings are for adults; check with the operator for child meal options.
Inform the operator at booking about allergies or dietary needs so the winery and lunch can be adjusted.
San Gimignano’s skyline of medieval towers reflects rival noble families’ power from the 12th–14th centuries; Siena’s civic layout centers on medieval communal life and the Palio horse race.
Many wineries here practice sustainable viticulture to reduce erosion and preserve soil health; travelers can support local producers by choosing estate tastings and avoiding single-use plastics.
Events in Italy operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
Book with Events in Italy
Book directly with Events in Italy for the best rates and real-time scheduling.
Reserve Now