Towers and Terroir: Private Tour of San Gimignano with Guide & Premium Wines of Chianti

Explore the medieval streets of San Gimignano with a local guide and savor the world-class wines of Castello di Fonterutoli

Travel through the golden hills of Tuscany, where ancient history and renowned winemaking converge in a day of unforgettable experiences. This full-day tour takes you from the celebrated cellars of Castello di Fonterutoli to the striking medieval towers of San Gimignano, offering a perfect balance of cultural discovery and indulgent flavors.

Morning: Castello di Fonterutoli – A Legacy in Every Glass​

Your adventure begins as your private driver collects you from accomodation, leading you through the rolling vineyards of Chianti Classico for a wine tasting and refined Tuscan lunch at Castello di Fonterutoli. Upon arrival, you'll be greeted by your host then delve into the fascinating world of Tuscan winemaking with an insider’s tour of Castello di Fonterutoli, owned by the Mazzei family for 24 generations. Along the way, you'll discover how this historic estate marries centuries-old tradition with modern innovation.

Tour the winery’s atmospheric cellars carved into the hillside, where oak barrels quietly age some of Chianti’s most esteemed wines. Learn how the Mazzei family helped define the Chianti identity, contributing to the original wine formula dating back to 1398.

Your experience concludes with a guided tasting of Fonterutoli’s exceptional labels, including their acclaimed Chianti Classico. Your host will guide you through each pour, sharing how the unique terroir and meticulous craftsmanship come together in the glass.

Lunch: A Tuscan Feast at Castello di Fonterutoli

Following the tasting, indulge in a gourmet, multi-course meal that celebrates the flavors of the region at the estate’s acclaimed restaurant. Seasonal ingredients and traditional recipes are paired with estate wines to create a dining experience that is both rustic and refined. With sweeping views and a deep-rooted winemaking tradition, this estate is a perfect setting for a culinary interlude.

Afternoon: San Gimignano's Towering Legacy

After a morning of wine tasting and lunch in Chianti, your journey continues into the idyllic Tuscan countryside to the  legendary hill town of San Gimignano. Often called the “Medieval Manhattan” for its impressive skyline of stone towers, you'll feel like you’ve stepped back in time as your expert local guides leads you through this UNESCO World Heritage Site. Admire the town’s iconic towers, 13 of the original 72 still stand, as symbols of San Gimignano’s former power and prestige.

Visit Piazza della Cisterna, the heart of the town, surrounded by Romanesque and Gothic façades, and stop by the Collegiata di Santa Maria Assunta, a Romanesque cathedral adorned with 14th-century frescoes by artists of the Sienese school. Wander through cobbled streets lined with artisan boutiques and ancient buildings, while your guide shares the rich history behind the town’s noble families, rivalries, and architectural wonders.

As the sun dips over the vineyards, your driver will escort you back to your accomodation, leaving you with lasting memories of medieval splendor, world-class wines, and the soul-stirring beauty of the Tuscan countryside.

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