THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Spend a full day exploring Siena, Monteriggioni and San Gimignano from Florence, with expert local guiding and a winery tasting. Expect medieval streets, hilltop vistas and a hands-on primer in Chianti wine culture.
Spend a full day exploring Siena, Monteriggioni and San Gimignano from Florence, with expert local guiding and a winery tasting. Expect medieval streets, hilltop vistas and a hands-on primer in Chianti wine culture.
Book with Keys Of Italy / Florence
Book directly with Keys Of Italy / Florence for the best rates and real-time scheduling.
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Operated by Keys Of Italy / Florence · Florence, Tuscany
Morning light slides over Florence as a premium minivan pulls away from the Arno, steering you into the folded hills of Chianti where vineyards lean toward the sun and olive trees keep a patient watch. The day unfolds as a sequence of hilltop towns—Siena's shell-shaped Piazza del Campo, Monteriggioni's circular battlements, and San Gimignano's ragged skyline of stone towers—each place offering a different chapter of medieval life.
moderate.
9–10 hours.
Suitable for travelers in average fitness—requires walking on cobbles, short uphill sections and standing during tastings.
Yes—the tour departs from Florence; exact pickup point is provided at booking and the tour returns to Florence the same evening.
Yes—an organized tasting at a local winery is included, and it typically covers several regional wines and local olive oil.
Children are welcome and strollers are permitted, but cobbled streets and stairs can make navigation challenging; infant seats are available in the vehicle.
Yes—the schedule includes free time in Siena and San Gimignano for independent visits, shopping or cathedral entry (admissions may be separate).
Siena, San Gimignano and Monteriggioni preserve distinct medieval roles—Siena’s civic rivalry (the Palio), San Gimignano’s tower-building families, and Monteriggioni’s defensive ring dating to the 13th century.
Vineyards and rural roads face pressure from tourism; stick to paths, avoid picking fruit and support local producers to keep landscapes intact.
Keys Of Italy / Florence operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
Book with Keys Of Italy / Florence
Book directly with Keys Of Italy / Florence for the best rates and real-time scheduling.
Reserve Now