Experience the absolute best of Tuscany on this immersive full-day tour from Florence. Designed for travelers who want to dive deep into the heart of Italian history, this 8-hour adventure takes you through the rolling vineyards of the Chianti countryside to visit two of Italy’s most prestigious UNESCO World Heritage sites: Siena and San Gimignano.
Your journey begins with a scenic drive featuring a stop at the iconic Piazzale Michelangelo for a breathtaking panoramic view of Florence. From there, we head south into the golden landscapes of Tuscany. Your first major destination is the medieval masterpiece of Siena. With skip-the-line access to the stunning Siena Cathedral, you will marvel at its Romanesque-Gothic architecture and intricate marble floors. You will then walk the historic path of the Via Francigena and stand in the heart of the city, the shell-shaped Piazza del Campo, home to the world-famous Palio horse race.
After enjoying some free time to shop for artisan crafts or enjoy a traditional Tuscan lunch, we travel to the 'Medieval Manhattan'—San Gimignano. Renowned for its breathtaking skyline of ancient stone towers, this hilltop town offers a glimpse into the Middle Ages like nowhere else. Wander the cobbled alleys, soak in the views of the surrounding hills, and treat yourself to a world-champion gelato before our comfortable return to Florence.
This tour is perfect for history buffs, photography enthusiasts, and anyone dreaming of an authentic Tuscan experience. With private transportation and a knowledgeable English-speaking driver, you will enjoy a seamless, stress-free day. We also provide a digital map to help you navigate the hidden gems of both cities during your free time. Whether you choose to explore independently or opt for a professional guide, this day trip promises a perfect blend of culture, art, and local flavors.
Wear comfortable walking shoes as both Siena and San Gimignano feature historic cobblestone streets.
Bring your camera! The panoramic view from Piazzale Michelangelo and the towers of San Gimignano are perfect for photography.
Don't miss the gelato in San Gimignano—it's widely considered some of the best in the world!
Choosing this tour means opting for a premium, stress-free experience that maximizes your time in Tuscany. Unlike crowded bus tours, our service prioritizes comfort and flexibility, allowing you to explore at your own pace while benefiting from local expertise. By combining the artistic grandeur of Siena with the charming, tower-filled skyline of San Gimignano, you get a comprehensive overview of the region's history and beauty. With included skip-the-line access and a curated digital map, we ensure you spend your day making memories rather than waiting in queues.
Lunch is not included, allowing you the flexibility to choose your own dining experience. We can provide recommendations for traditional Tuscan trattorias, or you can opt for our optional lunch add-on in the heart of Siena.
The tour involves a moderate amount of walking on historic cobblestone streets. We recommend wearing comfortable footwear to fully enjoy the historic centers of both cities.
