Leave the bustle of Florence behind for a day of pure Tuscan magic, where medieval history, stunning landscapes, and world-renowned wine traditions come to life. This comprehensive day trip is a curated journey through the heart of Tuscany, revealing its most iconic cities and its most cherished flavors. You’ll explore two of the region’s most famous hilltop towns, immerse yourself in centuries of history, and, as the highlight of your day, indulge in an authentic Tuscan lunch and wine tasting at a celebrated Chianti winery.

Your adventure begins with a scenic drive through the idyllic Tuscan countryside, a patchwork of rolling green hills, sun-drenched olive groves, and winding cypress-lined roads. Your first stop is the magnificent city of Siena. Stepping into Siena is like stepping back in time. With your expert guide, you’ll wander its winding cobblestone streets, marvel at the Piazza del Campo—the famous shell-shaped square where the historic Palio horse race takes place—and admire the stunning black and white striped marble facade of the Duomo. After your guided tour, you’ll have free time to explore the city at your own pace, perhaps grabbing a coffee in the piazza or visiting the impressive Siena Cathedral on your own.

Next, you’ll journey to the heart of the Chianti wine region, a place revered worldwide for its wines. This is where the true sensory experience of the day unfolds. You’ll arrive at a traditional, family-run Chianti winery and be welcomed with warm Italian hospitality. A guided tour will lead you through the vineyards, where you’ll learn about the unique terroir and the Sangiovese grape that forms the foundation of Chianti wine. You’ll also explore the aging cellars, where the wine rests in large oak barrels, soaking in the history of the estate.

The highlight of the winery visit is a traditional Tuscan lunch and an extensive wine tasting. Settle in for a delicious meal featuring local specialties, such as cured meats, artisan cheeses, and fresh pasta. Each course is expertly paired with a selection of the winery’s finest products. You’ll taste several varieties of wine, including the bold and rustic Chianti, and perhaps even a Super Tuscan or a sweet Vin Santo. You’ll also have the opportunity to sample locally produced olive oil and balsamic vinegar, adding another layer to your culinary adventure. The meal is a celebration of Tuscan flavors, enjoyed with a breathtaking view of the surrounding vineyards—an experience that is both educational and deeply satisfying.

After your delicious feast, you’ll travel to the enchanting medieval town of San Gimignano. Often called the “Medieval Manhattan” because of its iconic towers, this UNESCO World Heritage site is a fairy-tale town frozen in time. You’ll have free time to explore its charming piazzas, browse the unique artisan shops, and climb one of its famous towers for panoramic views of the Tuscan landscape. And for those with a sweet tooth, San Gimignano is home to a world-champion gelato shop, a perfect treat to end your exploration.

This day trip is a seamless blend of art, history, and gastronomy. It offers a chance to see three of Tuscany’s most beautiful destinations in one day, with the unforgettable experience of a true Tuscan lunch and wine tasting at a renowned Chianti winery. It’s a complete immersion into the heart of Italy, leaving you with lasting memories and a deeper appreciation for the beauty and flavors of this extraordinary region.

Highlights of Siena, San Gimignano, and a Chianti Winery

• Hearty farmhouse lunch at a winery overlooking the Typical Tuscan countryside
• Admire the medieval architecture of Siena and its gothic-style Cathedral
• Explore the squares, churches, and the magnificent towers of San Gimignano
• See the Leaning Tower of Pisa and other impressive marble monuments in Pisa

• Expert guide
• Guided walking tour of Siena
• Entry ticket to Siena Cathedral
• Farmhouse lunch at a winery estate in Chianti (if lunch option selected)
• Wine tasting of 4 regional wines (if lunch option selected)
• Free time in Siena, San Gimignano, and Pisa

• Hotel pickup and drop-off
• Leaning Tower of Pisa entry ticket

Meet in front of the Santa Maria Novella train station by the taxi stand, which is located right across the street from the McDonald’s outside the station.

Not suitable for

• People with mobility impairments

What to bring

Comfortable shoes

Know before you go

• If the Siena Cathedral is closed for religious services, the Palazzo delle Papesse will be visited instead
• Vegetarian option is available, but we regret that gluten free or other alternative dietary requirements cannot be catered for
• If you are leaving Florence by train after the tour or need to get off at Pisa to catch a flight or train from there, you can bring your luggage with you. It is recommended that you book any rail travel from Florence after 9:00 PM to allow time for any delays on the return journey