Memorable Experiences & Highlights in Siena

Accessible from inside the cathedral, this room is an explosion of vibrant, perfectly preserved Renaissance colour. It was commissioned to house the precious manuscript collection of Pope Pius II, a native of the city. The walls are entirely covered in brilliant frescoes painted by Pinturicchio, depicting the adventurous life of the Pope. The ceiling shines with intricate gold detailing, and the illuminated choir books displayed around the room are genuine works of art. It is a dazzling visual experience that contrasts sharply with the darker, gothic atmosphere of the main church.

This massive, solitary wall of striped marble stands as a haunting monument to the city's thwarted ambitions. It was intended to be the facade of the 'New Cathedral', a project designed to dwarf the existing church, but was abandoned forever when the plague decimated the population in 1348. Today, visitors can climb the narrow, winding stairs inside the wall via the cathedral museum. Reaching the top grants what is arguably the most spectacular, vertigo-inducing view over the entire city and the rolling hills beyond.

Originally built to shelter weary pilgrims traveling the Via Francigena, this sprawling complex served as a hospital for nearly a thousand years. Today, it operates as a fascinating, multi-layered museum complex. Exploring its vast halls reveals magnificent frescoes depicting medieval medical care and charity work. Beneath the main floors lie ancient, cavernous cellars and an archaeological museum housing Etruscan relics. It is a profound monument to the city's long history of civic duty and artistic patronage.

Housed inside a stunning 15th-century palace, this gallery contains the most important collection of 'gold-ground' Sienese paintings in the world. It showcases the unique local style that prioritised mystical elegance and rich colours over the mathematical perspective pursued in rival Florence. Masterpieces by Duccio, Simone Martini, and the Lorenzetti brothers fill the quiet, chronologically arranged rooms. The upper floors offer not only exquisite art but also fantastic views over the city rooftops. It is an absolute must-visit for anyone interested in medieval and early Renaissance art.

Built around the humble childhood home of Italy's famous mystic, this sanctuary is a complex of beautifully decorated chapels and courtyards. Walking through the rooms provides insight into the intense spiritual life of a woman who advised popes and significantly influenced 14th-century politics. The sanctuary preserves the stone stairs where she is said to have stumbled during a vision, and the small cell where she slept. Intricate majolica tiles and stunning frescoes decorate the walls, turning a simple house into a profound spiritual monument.

The distinct shell shape of this central square forms the physical and social heart of the city. Divided into nine segments reflecting the historical Council of Nine, the brick-paved expanse slopes gently downwards like a massive amphitheatre. It is entirely surrounded by uniform, elegant Gothic palaces, creating a sense of enclosed, theatrical beauty. Twice a year, it transforms into a frantic dirt racetrack for the legendary Palio. On normal days, it is the perfect place to sit on the warm bricks and watch the world go by.

This vast, austere brick church dominates the western hill of the city with its formidable, fortress-like presence. Inside, the massive, unadorned nave was designed to hold enormous crowds who came to hear the Dominican friars preach. The main draw is the ornate Renaissance chapel containing the mummified head of Saint Catherine, the city's revered patron saint. The church also features authentic frescoes portraying the saint, painted by artists who actually knew her in life. The terrace outside provides one of the finest panoramic views of the cathedral.

Situated at the top edge of the main square, this rectangular fountain was an engineering marvel when it first brought water to the city centre in 1342. The beautifully carved marble panels that line it are 19th-century copies of the original masterpieces created by Renaissance sculptor Jacopo della Quercia. The water flows constantly, providing a refreshing stop for both locals and pigeons alike. Its name, meaning 'joy', reflects the immense celebration that occurred when clean water finally reached the high urban plateau.