Small Group Tuscany Wine Tour: 2 Wineries, 2 Wine Tastings & Chianti Views
Taste the soul of Tuscany across rolling Chianti hills, storied cellars, and the medieval skyline of San Gimignano.
This Tuscany wine tour takes small groups through two distinct wineries in the Chianti region, offering guided tastings, cellar visits, and sweeping countryside views — all without the concern of driving on unfamiliar roads.
Guests move from a hillside estate producing Chianti Classico and Super Tuscan wines to a family winery celebrated for its D.O.C.G. Vernaccia white wine, framed by the iconic towers of San Gimignano. Along the way, a passionate wine producer shares the craft behind each bottle, from vine to glass.
The day concludes with a leisurely walk through San Gimignano, a UNESCO World Heritage town whose fourteen medieval towers have defined the Sienese skyline for centuries. The tour suits travellers who want genuine wine education paired with authentic Tuscan scenery, not a hurried checklist experience.
Tour Highlights
Taste five wines at the first winery, including Chianti Classico, Vernaccia, and Super Tuscan varieties selected by the producer.
Sample a 30-year-old balsamic vinegar and truffle extra virgin olive oil alongside your wine flight.
Walk through working vineyards and historic cellars with winemakers who explain both wine and olive oil production.
Explore San Gimignano and its fourteen medieval towers, including the option to climb for panoramic countryside views.
Purchase local wines and artisan products directly from the winery at producer prices to take home or ship abroad.
Enjoy unobstructed views over the Chianti hills and the silhouette of San Gimignano's towers from the second winery.
Itinerary
Guests choose their starting point at booking. Free parking is available at the Tuscany on Wheels office, located a short distance outside San Gimignano.
Arrive at a winery approximately one hour outside Florence for a guided tasting of five wines, including Chianti Classico, Vernaccia, and a Super Tuscan. A 30-year-old balsamic vinegar and truffle olive oil are also served.
A local family winery in the San Gimignano wine zone welcomes the group for a tour of its vineyards and cellars. Three wines are poured: Vernaccia di San Gimignano white, a rosé, and Chianti Colli Senesi D.O.C.G.
A free-roaming visit to the historic centre gives guests time to explore the medieval towers, browse local shops, or climb for views across the Val d'Elsa.
The tour ends at the Tuscany on Wheels office for those who started there, or in San Gimignano for guests who chose that as their departure point.
What Is Included
Included
- Transportation throughout the tour
- Guided visit to two wineries
- Tasting of five wines at the first winery
- Tasting of three wines at the second winery
- 30-year-old balsamic vinegar sample
- Truffle extra virgin olive oil sample
- Guided cellar and vineyard tour at second winery
- Free time in San Gimignano
Not Included
- Food and meals
- Personal purchases at the winery shop
- Tower entrance fees in San Gimignano
- Gratuities for guides
Important Information
Ready to Explore Tuscany's Wine Country?
Secure your place on this small group Chianti wine tour and spend a day among vineyards, cellars, and medieval towers with knowledgeable local producers as your guides.
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