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 driver and expert Walks of Italy guide, 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, skip-the-line entry to Siena’s highlights, 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. With your private guide, you’ll 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. Next, you’ll 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:

• 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, immersive way to see Tuscany from Florence.