Private Tour of Chianti with Wine Tastings
Medieval hilltop towns, rolling Chianti vineyards, and UNESCO-listed skylines — all in one unforgettable day.
This Private Tour of Chianti takes you through the heart of Tuscany, weaving together medieval architecture, world-class wines, and some of Italy's most iconic hilltop destinations in a single, carefully crafted eight-hour journey.
Traveling in a luxury vehicle, you will move comfortably between Monteriggioni, Siena, San Gimignano, and the Chianti wine country, with Pisa as a final flourish before returning to Florence. The private format means the pace is yours to set, and every stop is chosen to offer both cultural depth and sensory pleasure.
A professional tour guide can accompany you on request, sharing local knowledge at every landmark. Lunch arrangements are flexible — choose your own restaurant or lean on expert recommendations tailored to the region's culinary traditions.
Tour Highlights
Walk the intact medieval walls of Monteriggioni, one of Tuscany's best-preserved fortified villages.
Explore Siena's Piazza del Campo and admire the Gothic grandeur of the Palazzo Pubblico and Siena Cathedral.
Discover San Gimignano's UNESCO-listed medieval towers and taste its celebrated Vernaccia white wine.
Tour a working Chianti wine estate and sample high-quality wines, local snacks, and fresh olive oils with the owner.
Travel panoramic Chianti roads through picture-perfect Tuscan landscapes between every destination.
Visit Pisa's Piazza dei Miracoli and see the Leaning Tower, the Cathedral, and the Baptistery up close.
Enjoy a fully private experience in a luxury vehicle, with an optional professional guide throughout.
Itinerary
Your journey begins in Monteriggioni, a hilltop village whose circular walls and towers have stood virtually unchanged since the 13th century. Stroll the rustic streets, pause for an espresso, and absorb the atmosphere of a place that feels genuinely removed from the modern world.
In Siena, follow your guide to Piazza del Campo, the shell-shaped square that hosts the famous Palio horse race each year. Nearby, the Piazza del Duomo presents the Cathedral — one of the finest examples of Italian Gothic architecture — before free time lets you explore the historic centre independently.
San Gimignano is known for two things: its cluster of medieval towers, declared a UNESCO World Heritage Site, and its Vernaccia di San Gimignano, among Italy's most celebrated white wines. Free time here allows for independent exploration of the narrow streets and sweeping hilltop viewpoints.
At the heart of the Chianti Classico zone, you will visit a working wine estate and learn the production process directly from the owner. The tasting covers a selection of quality Chianti wines paired with local snacks and freshly pressed olive oil.
The final stop is Pisa's celebrated Piazza dei Miracoli, where the Baptistery, the Cathedral, and the iconic Leaning Tower form one of the most recognizable ensembles in Italian architecture. After time to admire the square, your vehicle returns you to Florence.
What Is Included
Included
- Private luxury vehicle or minivan for the full day
- Professional driver throughout the tour
- Optional professional tour guide (upon request)
- Wine tasting at a Chianti estate with local snacks and olive oil
- Visits to Monteriggioni, Siena, San Gimignano, and Pisa
- Flexible lunch arrangements with local recommendations
Not Included
- Entrance fees to monuments and museums
- Lunch and personal food expenses
- Gratuities for guide or driver
- Travel insurance
Important Information
Reserve Your Private Chianti Tour
Secure your place on this private Tuscan day tour and enjoy a flexible, expertly guided journey through Chianti, Siena, San Gimignano, and beyond — tailored entirely to your group.
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