Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

Meeting point

Where

Check-in: 7.45am - Your guide will be holding a WALKABOUT TOURS sign, right by the taxi stand at Santa Maria Novella train station across from the outside McDonald's · Open in Google Maps

Departure

08:00, 08:30 daily; scheduled year-round (operator schedule, seats confirmed at checkout)

Return

This activity ends back at the meeting point

Pickup

No hotel pickup: everyone meets at the start point

Operator

Walkabout Florence Tours; booking and payment are completed on Viator

1. 1
   Siena

   Leaving Florence behind, the journey begins with a scenic drive through the rolling Tuscan countryside until the skyline of Siena appears, a perfectly preserved medieval city perched atop three hills. Known for its warm-toned brick buildings and Gothic character, Siena offers an immediate sense of stepping back in time.

   1h 30m
2. 2
   Piazza Salimbeni

   Upon arrival, a short walk leads to Piazza Salimbeni, a refined and quieter square framed by elegant palaces. At its center stands a statue of Sallustio Bandini, surrounded by the historic headquarters of one of the oldest banks in the world, giving the square a distinctly noble and intellectual atmosphere.

   20 min
3. 3
   Contrada della Torre

   As the tour continues, you’ll be introduced to the unique concept of the “contrade,” Siena’s historic districts. Each contrada has its own emblem, traditions, and fierce identity, all of which come to life during the famous Palio horse race. Walking through these neighborhoods reveals flags, fountains, and symbols that tell stories of centuries-old rivalries and pride.

   20 min
4. 4
   Piazza del Campo

   The heart of Siena reveals itself in Piazza del Campo, a vast shell-shaped square that gently slopes toward the Palazzo Pubblico. This is the stage for the Palio and one of the most unique public spaces in Europe, where locals and visitors alike gather to relax and soak in the atmosphere.

   20 min
5. 5
   Duomo di Siena

   The route then leads uphill to the magnificent Duomo di Siena, a masterpiece of Italian Gothic architecture. Its striking black-and-white marble façade and richly decorated interior—featuring intricate floors, sculptures, and works by masters like Michelangelo—make it one of the most breathtaking churches in Italy.

   30 min
6. 6
   Fattoria Poggio Alloro

   Next, we visit an organic, family-run wine estate—one of the true highlights of the day. Here, you’ll enjoy a relaxed and informal tasting experience, sampling regional wines such as Chianti, Vernaccia, and the traditional Tuscan dessert wine, Vin Santo. This is followed by a generous lunch featuring authentic local flavors, all served with sweeping views over the surrounding countryside. It’s the perfect moment to unwind, connect with fellow travelers, and savor fresh, organic farm produce, including homemade pasta, artisanal cured meats like prosciutto and salami, local cheeses, a crisp garden salad, and classic Tuscan biscotti.

   2h
7. 7
   San Gimignano

   Leaving the winery, the journey continues through vineyards and olive groves to San Gimignano, often called the “Medieval Manhattan” for its skyline of ancient towers. This UNESCO-listed hill town offers a striking contrast with its vertical silhouettes rising above the countryside.

   1h 30m
8. 8
   Piazza Della Cisterna

   Entering the town, you’ll find yourself in Piazza della Cisterna, a triangular square named after the well at its center. Surrounded by towers and medieval houses, it’s a picturesque and lively spot, perfect for pausing and taking in the timeless ambiance.

   20 min
9. 9
   Piazza del Duomo

   A few steps away lies Piazza del Duomo, the town’s religious and civic center. Here, the Collegiate Church stands opposite the Palazzo Comunale, creating a harmonious space that reflects the balance of power in medieval life.

   20 min
10. 10
    Rocca of Montestaffoli

    The visit continues to the Rocca di Montestaffoli, a fortress offering panoramic views over the surrounding countryside. From this vantage point, the rolling hills, vineyards, and distant villages create a quintessential Tuscan landscape.

    20 min
11. 11
    Pisa

    In the afternoon, the itinerary heads west toward Pisa, a historic maritime republic known worldwide for its architectural treasures. The city’s atmosphere blends academic energy—thanks to its university—with centuries of history.

    1h 15m
12. 12
    Piazza dei Miracoli

    Arriving in Pisa, you’ll step into the remarkable Piazza dei Miracoli, a vast green space where some of Italy’s most celebrated monuments stand in striking harmony. This UNESCO World Heritage Site showcases an extraordinary collection of Romanesque architecture.

    30 min
13. 13
    Leaning Tower of Pisa

    The visit naturally culminates at the iconic Leaning Tower, Pisa’s most famous landmark. Instantly recognizable for its distinctive tilt, this elegant white-marble bell tower has fascinated visitors for centuries. Whether admired from afar or up close, it provides the perfect opportunity for memorable photos and a fitting finale to a day rich in history, culture, and unforgettable landscapes.

    30 min
14. 14
    Florence

    You will be dropped off in Florence at around 8.30pm with a camera full of pictures, a stomach full of hearty Tuscan food and a host of new friends.

    1h 15m

About this tour, from the operator