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The classic Tuscany trio, without a rental car.
A private day trip through the Tuscan countryside to Siena and San Gimignano, finishing with a stop in Chianti wine country.
Enjoy the scenic drive through the Tuscan countryside and hop out to capture photos along the way, venturing into Siena and San Gimignano to explore must-see medieval landmarks at your own pace and finishing in Chianti with an optional wine tasting at a local winery.
A popular starting point — every Voyzo itinerary is fully customizable, so we'll shape the order and stops around your group.
Hotel pickup included in Florence.
Explore both towns' landmarks at your own pace.
Finish the day with a tasting at a local winery.
Back to your hotel, home, or the airport — whenever your day wraps up.
A private day trip through the Tuscan countryside to Siena and San Gimignano, finishing with a stop in Chianti wine country. Enjoy the scenic drive through the Tuscan countryside and hop out to capture photos along the way, venturing into Siena and San Gimignano to explore must-see medieval landmarks at your own pace and finishing in Chianti with an optional wine tasting at a local winery.
Piazza del Campo's shell shape isn't decorative — the square is divided by white stone lines into nine segments, a deliberate nod to the Government of the Nine, the council that oversaw Siena through much of the 14th century as the piazza took its current form. Twice a year, on July 2 and August 16, the square's edges become a racetrack covered in tufa dust for the Palio di Siena, a bareback horse race first documented in 1656 and still contested today by riders representing the city's historic districts.
San Gimignano's skyline tells a quieter but equally competitive story: rival families here built increasingly tall stone towers between the 11th and 14th centuries as a show of power, reaching 72 towers at the town's medieval peak. Only 14 survive today, which is still enough to make the approach to San Gimignano one of the most recognizable hilltop views in Tuscany.
An optional stop in Chianti at the end of the day puts you in the territory once marked by the Lega del Chianti, a 14th-century Florentine militia whose black-rooster emblem — the Gallo Nero — still appears on Chianti Classico bottles today, a reminder that this landscape has been producing serious wine for a very long time.
Every Voyzo tour is a starting point — tell us what you have in mind and we'll build it.
