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

Highlights

Itinerary

1. 1

   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•Admission free

2. 2

   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 minutes•Admission free

3. 3

   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 minutes•Admission free

4. 4

   Pubblico Palace

   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 minutes•Admission free•See on map

5. 5

   Siena Cathedral

   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 minutes•Admission free•See on map

6. 6

   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.

   2 hours•Admission free

7. 7

   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•Admission free

8. 8

   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 minutes•Admission free

9. 9

   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 minutes•Admission free

10. 10

    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 minutes•Admission free

11. 11

    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•Admission free

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 minutes•Admission free•See on map

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 minutes•Admission free•See on map

14. 14

    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•Admission free

Meeting point

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

The map shows Florence. The exact meeting point is the address above.Open larger map

Pickup

• Everyone meets at the start point

Know before you go

• Infants and small children can ride in a pram or stroller
• Public transportation options are available nearby
• Infants are required to sit on an adult’s lap
• Travelers should have at least a moderate level of physical fitness
• Due to uneven surfaces, we cannot accept anyone with walking difficulties or using a wheelchair
• Vegetarian option is available, but we regret that gluten free or other alternative dietary requirements cannot be catered for
• It is recommended to book any rail travel from Florence after 9pm to allow time for any traffic delays on your return journey
• When the Duomo of Siena is closed for religious services, Palazzo delle Papesse will be visited instead
• Operates in all weather conditions, please dress appropriately
• Please note: For the Leaning Tower of Pisa children under the age of 8 are not admitted. Children between 8 and 12 years old must be accompanied by an adult and held by the hand at all times while you are in the Leaning Tower of Pisa. Teenagers between 13 and 18 years old must be accompanied by an adult while you are in the Leaning Tower of Pisa
• Classic Tour option includes the visit to Pisa but not the ticket to climb the Leaning Tower
• With Leaning Tower Tickets option also include the tickets to climb on the Leaning Tower in Pisa.
• Mobile or paper ticket accepted
• One per booking
• • Operates in all weather conditions, please dress appropriately • Due to uneven surfaces, we cannot accept anyone with walking disabilities or using a wheelchair • Please note: For the Leaning Tower of Pisa children under the age of 8 are not admitted. Children between 8 and 12 years old must be accompanied by an adult and held by the hand at all times while you are in the Leaning Tower of Pisa. Teenagers between 13 and 18 years old must be accompanied by an adult while you are in the Leaning Tower of Pisa • When the Duomo of Siena is closed for religious services, Santa Maria della Scala museum will be visited instead. • Vegetarians and gluten free can be catered for

Cancellation and refunds

For a full refund, cancel at least 24 hours before the scheduled departure time.

• Cancelled and fully refunded if the weather makes it unsafe
• Cancelled and fully refunded if too few travellers book