Grape Escape Winery Tour: Chianti, San Gimignano and Tuscan Flavors
Two wineries, eight wines, ancient towers, and the rolling hills of Tuscany — all in one unforgettable day from Florence.
This Tuscany winery day tour takes you through the heart of Chianti wine country and the medieval hilltop town of San Gimignano, combining hands-on tastings with genuine cultural discovery. Over seven hours, you will visit two acclaimed wineries, sample eight wines across multiple appellations, and explore one of Tuscany's most iconic historic centers.
The journey begins with a scenic one-hour drive from Florence into the Chianti Classico region, where a passionate local producer guides you through a tasting of four distinct wines alongside a 30-year-aged balsamic vinegar and truffle extra virgin olive oil. The setting is intimate, the knowledge is deep, and the experience is designed to sharpen your palate rather than simply fill your glass.
The second winery sits in the elevated countryside surrounding San Gimignano, a town listed as a UNESCO World Heritage Site for its extraordinary medieval skyline of ancient towers. Here, winemakers lead you through vineyards and underground cellars, revealing the traditions behind D.O.C.G. Vernaccia white wine, rose, and Chianti Colli Senesi before you explore the town's cobblestone streets at your own pace.
With a maximum small-group format, an expert guide fluent in Tuscan history and viticulture, and a relaxed mid-morning departure, this tour suits travelers who want depth, scenery, and genuine local flavor without an early alarm call.
Tour Highlights
Taste eight wines across celebrated Tuscan appellations including Chianti Classico, Brunello di Montalcino, Super Tuscan, Vernaccia, and Chianti Colli Senesi D.O.C.G.
Sample a rare 30-year-aged balsamic vinegar alongside truffle and plain extra virgin olive oils, guided by producers who explain each product's origin and character.
Explore San Gimignano, the so-called Medieval Manhattan, with its landmark towers, Piazza del Duomo, and Romanesque Collegiata cathedral.
Travel through the rolling vine-covered hills of Chianti on a scenic drive enriched by your guide's stories about Tuscan history and landscape.
Enjoy traditional Tuscan snacks paired with the wines, and browse local products available for purchase or international shipping directly from the winery.
Receive practical wine education from working producers, learning to identify aromas, flavors, and the principles behind successful food and wine pairing.
Visit underground cellars at the second winery for an insider look at the production process behind two of Tuscany's most distinctive white and red wines.
Day Itinerary
Gather at Piazza della Calza near the historic Roman Gate of Florence and meet your guide, identifiable by a purple T-shirt. Brief introductions set a relaxed tone before the group boards transport for the Chianti region.
The one-hour journey south from Florence passes through terraced vineyards, silver-leafed olive groves, and cypress-lined ridges. Your guide provides context on Tuscan geography, wine classifications, and the day ahead.
At a family-run estate in the Chianti heartland, a passionate producer leads a structured tasting of four wines: Chianti Classico, Brunello di Montalcino, Super Tuscan, and a fourth selection. The session also covers 30-year-aged balsamic vinegar and truffle extra virgin olive oil, with guidance on recognizing aromas and balancing flavors.
The afternoon moves to an estate in the D.O.C.G. Vernaccia di San Gimignano appellation, where winemakers escort the group through working vineyards and vaulted cellars. Three wines are poured — Vernaccia white, rose, and Chianti Colli Senesi — accompanied by notes on seasonal viticulture and food pairing traditions.
Walk the medieval lanes of San Gimignano at your own pace, visiting the Piazza del Duomo, climbing the Torre Grossa for panoramic views, or sampling local saffron specialties from artisan producers. The town's compact scale makes it easy to explore independently within the allotted time.
The group reassembles for the one-hour return drive to Piazza della Calza, arriving back in Florence by late afternoon. Winery products purchased during the day can be taken home or arranged for international shipping.
What Is Included
Included
- Round-trip transport from Florence in air-conditioned vehicle
- Expert English-speaking guide for the full duration
- Guided visit to two Tuscan wineries
- Eight wine tastings across multiple D.O.C.G. and D.O.C. appellations
- Tasting of three extra virgin olive oils
- 30-year-aged balsamic vinegar tasting
- Traditional Tuscan snacks throughout
- Cellar and vineyard tours at both estates
- Free exploration time in San Gimignano
Not Included
- Lunch or additional meals
- Personal purchases at wineries or shops
- Entrance fees to museums or monuments in San Gimignano
- Gratuities for guide or driver
- Travel insurance
Important Information
Reserve Your Spot on This Tuscany Wine Tour
Places on this small-group tour fill quickly, particularly during peak travel months. Secure your seat today and look forward to a day of rolling Tuscan scenery, artisan winemakers, and eight exceptional wines.
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