Siena, Monteriggioni, San Gimignano & Chianti Wine Tasting
A private journey through Tuscany's medieval towns, hilltop fortresses, and celebrated wine country
This private Tuscany day tour from Florence takes you through four of the region's most celebrated destinations in a single, well-paced itinerary. Travel in comfort across rolling hills, ancient stone streets, and sun-drenched vineyards without the distraction of a large group.
The day moves between Monteriggioni's intact medieval walls, Siena's UNESCO-listed historic center, and the vine-covered landscapes of the Chianti Classico zone. Each stop offers a distinct character — military architecture, Gothic urban planning, and centuries-old winemaking tradition side by side.
San Gimignano rounds out the experience with its cluster of medieval towers and one of Italy's most recognized gelaterias. The pace is relaxed, the route is private, and the setting is consistently Tuscan at its most photogenic.
Tour Highlights
Walk the ancient walls of Monteriggioni, one of Italy's best-preserved medieval fortified villages.
Explore Siena's UNESCO-listed historic center, including the iconic Piazza del Campo and the Gothic Cathedral.
Enjoy a guided wine tasting at a Chianti winery, featuring local varieties including Chianti Classico.
Sit down to a traditional Tuscan lunch prepared with fresh, locally sourced ingredients at the winery.
Discover San Gimignano's medieval towers and the lively Piazza della Cisterna, a UNESCO World Heritage Site.
Travel the scenic Chianti countryside in a private vehicle with no shared itinerary constraints.
Itinerary
Your first stop is Monteriggioni, a circular hilltop village encircled by a complete medieval wall dating to the 13th century. Walk the perimeter, take in panoramic views of the Sienese countryside, and explore the quiet interior of this remarkably intact fortress village.
Siena's UNESCO-listed city center rewards unhurried exploration. The visit centers on Piazza del Campo — the distinctive shell-shaped square famous for the Palio — and the Cathedral of Siena, a landmark of Italian Gothic architecture with an optional interior entry.
At a winery in the Chianti Classico zone, a guided tasting introduces you to the region's signature wines. A traditional Tuscan lunch follows, featuring seasonal ingredients prepared in the local style.
The afternoon visit to San Gimignano focuses on Piazza della Cisterna and the medieval tower skyline that defines this UNESCO-listed town. Time is available to browse artisanal shops or stop at Gelateria Dondoli, internationally recognized for its award-winning gelato.
The return drive across the Tuscan countryside brings the day to a relaxed close. You arrive back in Florence at the end of a full itinerary covering four distinct destinations.
What Is Included
Included
- Private transportation from and to Florence
- Professional private guide throughout the day
- Guided wine tasting at a Chianti winery
- Traditional Tuscan lunch at the winery
- Entrance to Monteriggioni village
- All transfers between stops
Not Included
- Siena Cathedral interior entry (optional, paid on site)
- Personal expenses and souvenirs
- Gratuities for the guide and driver
- Any food or drinks beyond those specified
Important Information
Reserve Your Private Tuscany Day Tour
Secure your spot on this private full-day tour and explore Siena, Monteriggioni, San Gimignano, and the Chianti wine country at your own pace. Availability is limited for private departures.
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