Ramble Through the Rolling Hills of Chianti: San Gimignano, Lunch and Wine Tasting
A private journey through cypress-lined roads, medieval towers, and a Tuscan vineyard table set just for you.
This private Chianti wine tour from Florence takes you deep into one of Italy's most celebrated landscapes, where rolling hills, ancient villages, and world-class wines converge into a single unforgettable day. Beginning with a panoramic stop above Florence, the route winds through the heartland of Chianti before arriving at a real working Tuscan farm for lunch and guided wine tasting.
The itinerary is designed for travelers who want more than a glimpse of Tuscany. From the bronze-gilded viewpoint at Piazzale Michelangelo to the medieval skyline of San Gimignano and the shaded rows of a family vineyard, every stop builds on the last to deliver a layered, authentic experience of the region.
Because this is a fully private tour, the pace is set by you and your group. Your driver is dedicated to your party for the entire day, ensuring flexibility at each destination without the constraints of a shared group schedule.
The vineyard lunch is a highlight in itself: homemade pasta, bruschetta, aged pecorino, and a guided tasting of eight wines drawn from the estate and surrounding appellations, all enjoyed within sight of San Gimignano's famous towers.
Tour Highlights
Sweeping panoramic views of Florence from Piazzale Michelangelo before departing into the Chianti countryside.
Guided exploration of San Gimignano, a UNESCO World Heritage medieval town famous for its preserved tower skyline.
Climb the Torre Rognosa for a 360-degree panorama over the Sienese hills and the Chianti wine country below.
Sample award-winning gelato at Gelateria Dondoli, consistently ranked among the finest gelaterias in the world.
Sit down to a three-course Tuscan farmhouse lunch featuring lasagna, homemade pasta, bruschetta, and aged pecorino cheese.
Eight guided wine tastings covering Chianti, Brunello, Sangiovese, Vernaccia, and more, led by an on-site sommelier.
Fully private door-to-door service with a dedicated driver picking you up and returning you directly to your Florence accommodation.
Itinerary
Your private driver collects you directly from your hotel, B&B, or apartment in Florence. No need to navigate public transport or meeting points in an unfamiliar city.
The first stop offers one of the most celebrated views in Italy, looking out over Florence's terracotta rooftops and the Arno River. Bronze casts of Michelangelo's most iconic sculptures frame the square, providing context before you head into the countryside.
The route south passes through classic Chianti scenery: cypress avenues, olive groves, and terraced vineyards stretching toward the horizon. Your guide will explain the significance of the Black Rooster, the historic emblem of the Chianti Classico wine-producing zone.
Approximately one hour is reserved for independent exploration of this remarkably preserved medieval town. Ascend the Torre Rognosa for sweeping views, wander the stone lanes, and stop at Gelateria Dondoli for a taste of what is widely regarded as the finest artisan gelato in the country.
The afternoon is spent at a working Tuscan farm set against a backdrop of San Gimignano's tower silhouette. A sommelier leads a tasting of eight wines alongside a full farmhouse lunch, with additional tastings of estate olive oils and aged balsamic vinegar available.
Your driver returns you to your Florence accommodation at approximately 4:00 pm, concluding a full day in the Chianti countryside without the logistics of self-guided travel.
What Is Included
Included
- Private driver and vehicle for the full duration
- Door-to-door hotel pickup and drop-off in Florence
- Stop at Piazzale Michelangelo
- Free time in San Gimignano including Torre Rognosa access
- Guided visit to a working Tuscan vineyard
- Three-course Tuscan farmhouse lunch (lasagna or homemade pasta, bruschetta, pecorino)
- Eight guided wine tastings with sommelier
- Olive oil and balsamic vinegar tastings
Not Included
- Gratuities for driver and vineyard staff (discretionary)
- Personal purchases at San Gimignano shops or market
- Gelato at Gelateria Dondoli (own expense)
- Travel insurance
- Additional beverages beyond the included wine tastings
Important Information
Reserve Your Private Chianti Experience
Secure your place on this private day tour through the Chianti hills, San Gimignano, and a working Tuscan vineyard. Availability is limited by the private nature of the experience, so early booking is advisable, particularly during the spring and autumn travel seasons.
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