All Florence Tours in October 2025
1 Trip in Florence during October 2025 with 13 Reviews
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San Gimignano, Siena & Chianti from Florence - October 2025
Step Into the Soul of Tuscany: A Full-Day Wine & Culture Journey
Leave the bustle of Florence behind and set off on an unforgettable day trip deep into the heart of Tuscany, where time seems to slow down and every hilltop town tells a story. This carefully curated experience takes you through the rolling vineyards of Chianti, the medieval magic of Siena, and the timeless charm of San Gimignano.
Wander Through Siena’s Storied Streets
Your adventure begins in the enchanting town of Siena, a place where history whispers from every stone. Meander through its labyrinth of narrow alleys, soak in the atmosphere of the famous Piazza del Campo—home to the legendary Palio horse race—and stand in awe before the majestic Cathedral of Santa Maria Assunta, a Gothic masterpiece brimming with centuries of artistry and devotion.
Taste Tuscany: Wine, Food, and Tradition
From Siena, we journey into the sun-drenched hills of Chianti, the beating heart of Tuscan wine country. Here, amid vineyards that stretch to the horizon, you'll be welcomed to a traditional estate for a relaxing lunch and exclusive wine tasting. Savor the flavors of authentic Tuscan cuisine paired with world-class wines like Chianti Classico. Tour the wine cellars, learn the secrets of the winemaking process, and enjoy the warm hospitality of the countryside.
Discover the Towers of San Gimignano
Our final destination is San Gimignano, the “Medieval Manhattan” of Tuscany, famous for its skyline of ancient towers. A UNESCO World Heritage site, this hilltop village invites you to step back in time as you explore its cobbled lanes, artisan boutiques, and postcard-perfect piazzas. And yes—make time to indulge in what many say is the best gelato in all of Italy.
Getting There
Your journey begins in Florence at Duomo Square, by the Colonna San Zanobi near the Baptistery of San Giovanni. Our friendly team will greet you before boarding a comfortable coach for a scenic ride through the Chianti countryside, complete with fascinating commentary along the way.
Small Group, Big Experience
With a maximum of 30 travelers, this intimate group tour offers a more personal connection to the land, its people, and its stories. By the end of the day, you’ll return to where it all began—back at Duomo Square in Florence—but you’ll carry the spirit of Tuscany with you long after the journey ends.
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