Private Tuscany Day Trip from Florence: Siena, San Gimignano & Chianti

Discover Three Stunning Destinations on a Perfectly Planned Tuscany Day Trip

Rolling hills, medieval towns, and world-class wines—this is the Tuscany of your dreams. On this Private Tuscany Day Trip from Florence, travel in comfort with a dedicated English-speaking driver, exploring Siena, San Gimignano, and the Chianti wine region on an all-inclusive Tuscan adventure.

With a farm-to-table lunch at a family-run vineyard, a walking tour of Siena with a local guide, and a seamless itinerary designed for maximum relaxation and discovery, this private tour is the best way to experience Tuscany in a single day.

Explore Siena’s History, Art & Medieval Traditions

Your day begins with Siena, one of Tuscany’s most breathtaking medieval cities. Once you arrive, you'll meet your private guide and discover:

• Piazza del Campo – The heart of Siena, home to the Palio horse race and the stunning Mangia Tower.
• Siena Cathedral (Optional Visit) – Admire the intricate black-and-white marble façade and breathtaking interiors.
• Local Traditions & Historic Streets – Stroll through centuries-old alleyways and discover the unique culture of Siena’s Contrade (neighborhoods).

Enjoy a Farmhouse Lunch & Wine Tasting in Chianti

No Tuscany tour is complete without exceptional food & wine. After saying goodbye to your local guide in Siena, you’ll hop back in the car and head to a family-run Chianti vineyard, where you’ll enjoy:

• A guided tour of the winery & vineyard – Learn the secrets behind Chianti Classico & Super Tuscan wines.
• A homemade, farm-to-table lunch – Savor a seasonally inspired Tuscan meal made with fresh local ingredients, paired with the vineyard’s finest wines.
• Tuscan Hospitality at Its Finest – Experience the warmth of true Italian countryside living with local winemakers.

Step Into a Fairytale in San Gimignano

With full bellies, you’ll continue to San Gimignano, one of Tuscany’s most famous hilltop villages. Here, you’ll have free time to explore on your own. These are some ideas of how to spend the perfect afternoon:

• Wander its medieval streets – Admire the town’s 14 historic towers and breathtaking panoramic views.
• Shop local artisan goods – Browse handmade ceramics, olive oils, and wines unique to this region.
• Taste Italy’s best gelato – Visit Gelateria Dondoli, a world-famous gelateria known for its award-winning flavors.

Why Choose a Private Tuscany Tour?

This private tour follows a carefully planned route, ensuring you experience Tuscany’s most beautiful towns and best wine regions in one effortless day. With a dedicated guide, private driver, and all logistics handled for you, it’s the most relaxing, personal, and immersive way to see Tuscany from Florence.