Chianti Private Tour with Dinner and Wine Tasting Experience
A golden evening among Tuscan hilltops, medieval towers, and vineyard tables
This Chianti private tour with dinner takes you from the streets of Florence into the rolling countryside of Tuscany, ending at a wine estate table beneath the open sky. Designed for travelers who want depth over crowds, this six-hour journey pairs culture, landscape, and cuisine into a single coherent experience.
The route winds through some of the most storied countryside in central Italy, passing through the vine-covered slopes that define the Chianti Classico zone before arriving at San Gimignano, a UNESCO-listed hill town whose medieval towers have shaped the Tuscan skyline for centuries. Free time here is unhurried, allowing genuine exploration rather than a rushed photo stop.
The evening concludes at a private wine estate in the Chianti hills, where a three-course Tuscan dinner is served alongside a structured wine tasting. Your private driver handles all logistics throughout, from the Florence pickup to the return transfer, so the experience remains relaxed from start to finish.
Tour Highlights
Explore San Gimignano, the medieval hill town nicknamed the Manhattan of Italy for its remarkable skyline of stone towers.
Watch the Tuscan sunset from the Rocca di Montestaffoli, a 14th-century fortress with panoramic views over vineyards and rolling hills.
Taste Vernaccia di San Gimignano, the first Italian wine to receive DOC certification, enjoyed before leaving the town.
Travel through the Chianti countryside, a landscape of olive groves, cypress rows, and continuous vineyards rarely seen from public transport.
Sit down to a three-course traditional Tuscan dinner at a charming wine estate in the heart of the Chianti hills.
Experience an exclusive wine tasting among the vineyards of Chianti, guided by the estate.
Travel in full comfort with a dedicated private driver who manages all transfers door to door.
Itinerary
Your private driver collects you directly from your accommodation in Florence and departs for the Tuscan countryside. The drive itself offers a gradual transition from the city into a landscape of olive groves and vine-covered hillsides.
Arrive in San Gimignano and explore at your own pace. Wander the narrow alleys of the historic center, discover the main square Piazza della Cisterna, and sample gelato from one of the town's award-winning shops.
Make your way to the Rocca di Montestaffoli, a 14th-century fortress perched above the town. From the top of its walls, the view spans the entire valley, with Tuscan hills and vineyards stretching to the horizon as the light fades.
Before leaving the town, enjoy a glass of Vernaccia di San Gimignano, the local white wine varietal that earned Italy's first DOC designation in 1966. It serves as a fitting introduction to the evening's wine focus.
Your driver takes you into the Chianti hills to a private wine estate, where a three-course Tuscan dinner is served alongside a dedicated wine tasting among the vineyards. The setting is intimate and the atmosphere unhurried.
Once dinner concludes, your private driver escorts you back to Florence in comfort. Drop-off is at your original pickup location or nearby accommodation.
What Is Included
Included
- Private round-trip transfer from Florence
- Professional private driver throughout
- Free time in San Gimignano
- Vernaccia wine tasting in San Gimignano
- Three-course traditional Tuscan dinner
- Wine tasting at the Chianti estate
Not Included
- Gratuities for driver or estate staff
- Personal purchases and souvenirs
- Additional beverages beyond the tasting
- Travel insurance
Important Information
Reserve Your Private Chianti Evening
This tour operates as a fully private experience, meaning the itinerary, pace, and atmosphere are shaped entirely around your group. Spaces are limited by nature of the format, so early booking is advisable, particularly during the spring and summer travel season.
Book Now
