• Siena - Departing from Florence, the adventure begins with a picturesque drive through the rolling hills of Tuscany until the skyline of Siena emerges, a beautifully preserved medieval city set atop three hills. Renowned for its warm-toned brick buildings and Gothic charm, Siena instantly transports visitors back in time.
• Piazza Salimbeni - Upon arrival, a brief stroll leads to Piazza Salimbeni, a sophisticated and tranquil square surrounded by elegant palaces. At its center stands a statue of Sallustio Bandini, encircled by the historic headquarters of one of the world’s oldest banks, lending the square a distinctly noble and intellectual ambiance.
• Contrada della Torre - As the tour progresses, the unique concept of the “contrade,” Siena’s historic districts, is introduced. Each contrada boasts its own emblem, traditions, and strong identity, all vividly displayed during the renowned Palio horse race. Exploring these neighborhoods reveals flags, fountains, and symbols that narrate tales of age-old rivalries and pride.
• Piazza del Campo - The heart of Siena is unveiled in Piazza del Campo, a vast shell-shaped square that gently slopes toward the Palazzo Pubblico. This is the venue for the Palio and one of Europe’s most distinctive public spaces, where locals and visitors gather to relax and soak in the atmosphere.
• Duomo di Siena - The path then ascends to the magnificent Duomo di Siena, a masterpiece of Italian Gothic architecture. Its striking black-and-white marble façade and richly adorned interior—featuring intricate floors, sculptures, and works by masters like Michelangelo—make it one of Italy’s most breathtaking churches.
• Fattoria Poggio Alloro - Next, the tour visits an organic, family-run wine estate—one of the day’s true highlights. Here, guests 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.
• San Gimignano - Departing the winery, the journey continues through vineyards and olive groves to San Gimignano, often referred to as 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.
• Piazza della Cisterna - Entering the town, visitors find themselves 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.
• Piazza del Duomo - Just 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.
• 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.
• Pisa - In the afternoon, the itinerary heads west toward Pisa, a historic maritime republic renowned worldwide for its architectural treasures. The city’s atmosphere blends academic energy—thanks to its university—with centuries of history.
• Piazza dei Miracoli - Arriving in Pisa, visitors 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.
• 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.
• Florence - Guests 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.

• Hearty farmhouse lunch with 4 wine tastings (for selected options only)
• Siena Cathedral entrance fee (for selected options only)
• Free time to explore the towns at your own pace
• Professional English speaking tour guide with you for the whole day
• In-vehicle air conditioning
• Guided walking tour of Siena with local city guide

• Gratuities
• Hotel pickup and drop-off
• Food and drinks, unless specified

• 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.

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