Medieval Tuscany & Wine Experience: Certaldo, San Gimignano & Volterra
Three medieval villages, one family winery, and the timeless landscapes of Tuscany in a single unforgettable day.
This Tuscany medieval villages day tour from Florence takes you through three of central Italy's most historically layered hilltop towns, combining Etruscan archaeology, UNESCO-listed towers, and a guided wine tasting at a local family-run winery.
The route passes through the rolling scenery of Chianti and Val d'Elsa before reaching Certaldo Alto, a terracotta-hued hilltop settlement that remains largely off the radar of mass tourism. From there, the itinerary moves to San Gimignano and its famous medieval skyline, then closes in Volterra, where Etruscan walls and alabaster ateliers share the same narrow streets.
A traditional Tuscan lunch at a working vineyard anchors the day, offering five wines paired with regional produce. The pace is relaxed, the group is small, and the guide is English-speaking throughout.
Tour Highlights
Walk the tower-lined streets of San Gimignano, a UNESCO World Heritage Site known as the Manhattan of the Middle Ages.
Explore Volterra's Roman Theatre, Etruscan ruins, and centuries-old alabaster workshops in one of Tuscany's most layered towns.
Stroll the cobbled lanes of Certaldo Alto, the serene hilltop birthplace of medieval writer Giovanni Boccaccio.
Taste five local wines including Vernaccia di San Gimignano, Chianti, and Super Tuscan varieties at a family-run winery.
Enjoy a traditional light lunch paired with bruschetta, pecorino cheese, cured meats, and homemade pasta or fresh salads.
Travel through the scenic Chianti hills and Val d'Elsa valley in a comfortable air-conditioned minivan with panoramic views.
Benefit from the expertise of a dedicated English-speaking guide who brings the region's medieval history to life throughout the day.
Itinerary Overview
Meet your guide in the heart of Florence and board a comfortable air-conditioned minivan. The drive west reveals the quintessential Tuscan countryside of Chianti and Val d'Elsa, with vineyard-covered slopes and hilltop villages appearing at every turn.
Arrive at this perfectly preserved medieval hilltop village, birthplace of the celebrated writer Giovanni Boccaccio. Wander terracotta-coloured streets lined with artisan shops and take in sweeping views of the surrounding Tuscan countryside largely untouched by mass tourism.
Explore the iconic stone towers and medieval squares of this UNESCO World Heritage Site. Your guide shares stories of the merchants and rival families who shaped this extraordinary town, and there is time to browse local shops or sample the award-winning gelato at Dondoli Gelateria.
Settle into a family-run winery surrounded by vineyards and olive groves for a guided tasting of five wines, including Vernaccia di San Gimignano and Chianti. The tasting is accompanied by a traditional light lunch of bruschetta, pecorino, artisanal cured meats, and homemade pasta or fresh salads.
Conclude the day in Volterra, where Etruscan walls, a well-preserved Roman Theatre, and a medieval fortress occupy the same hilltop. The town is equally known for its alabaster artisans, and the valley views from the upper streets provide a memorable close to the day.
Board the minivan for a relaxed journey back to the city. Drop-off is in the Florence city center, typically by evening.
What Is Included
Included
- Professional English-speaking guide for the full day
- Air-conditioned minivan transport throughout
- Guided tour of Certaldo Alto, San Gimignano, and Volterra
- Guided tasting of 5 local wines at a family-run winery
- Traditional Tuscan light lunch at the winery
- Small-group experience
Not Included
- Hotel pickup and drop-off
- Entrance fees to museums or monuments
- Gratuities for the guide (optional)
- Personal expenses and additional food or drinks
- Travel insurance
Important Information
Book Your Spot Today
Places on this small-group tour fill quickly, particularly during spring and summer. Secure your seat to explore three of Tuscany's finest medieval villages alongside a knowledgeable local guide and a memorable winery lunch.
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