Il Palio di Siena & Castel Monastero 2027

On arrival in Florence, you'll be met and transferred by private car to Castel Monastero, your home for the next three nights. Set amidst the gently rolling landscapes of the Tuscan countryside, Castel Monastero occupies a beautifully restored medieval village whose origins date back centuries. Surrounded by vineyards, woodland and olive groves, it offers a peaceful retreat within easy reach of Siena. Spend the remainder of the day settling in and enjoying the hotel's exceptional facilities and tranquil surroundings.

Today is yours to explore Siena, one of Tuscany's most captivating cities and a UNESCO World Heritage Site. Renowned for its remarkably preserved medieval character, Siena is a city of grand piazzas, winding lanes and architectural treasures. At its heart lies the magnificent Piazza del Campo, considered one of Europe's finest public squares and the stage for tomorrow's eagerly anticipated Palio. Elsewhere, discover the striking Siena Cathedral, admire the city's Gothic architecture or simply soak up the atmosphere from a café terrace. This evening, enjoy a traditional dinner in one of Siena's historic Contrada districts. These neighbourhood associations form the foundation of local life and are central to the identity and traditions of the Palio. Savor a menu of regional specialities before returning to Castel Monastero.

Today is dedicated to one of Italy's most extraordinary cultural spectacles. For centuries, the Palio has been far more than a horse race, its roots deeply woven into the identity of Siena and the fierce rivalries between the city's historic contrade. Across the day, the city comes alive with colourful traditions, religious ceremonies and age-old rituals as jockeys, horses and supporters prepare for the event's dramatic climax. To ensure the very best experience, return transfers between Castel Monastero and Siena are included, along with access to a private window overlooking Piazza del Campo. From this privileged vantage point, watch the historic square fill with anticipation as the elaborate Corteo Storico procession makes its way through the city, accompanied by flag bearers, costumed participants and displays of medieval pageantry. As the race approaches, the atmosphere reaches fever pitch before ten horses and their riders thunder around the Piazza del Campo in a thrilling bareback contest that lasts little more than a minute, yet represents centuries of tradition and community pride. During the afternoon, enjoy cocktails and refreshments before an included dinner showcasing regional specialities, while after the race you'll have the opportunity to witness the jubilant celebrations that erupt across Siena as the victorious contrada claims the coveted Palio banner and continues the festivities long into the night.

Enjoy a relaxed breakfast before your private transfer back to Florence Airport for your onward flight.