At Your Own Pace: Discovering Siena & Tuscany

Highlights

Inclusions

Itinerary

1. This extraordinary shell-shaped piazza has served as Siena's living room since the 14th century, its sloping brick pavement divided into nine segments representing the Council of Nine who governed during Siena's golden age. Twice each summer, the piazza transforms into a racetrack for the Palio, where bareback riders representing the city's seventeen contrade compete in a 90-second spectacle that has captivated Sienese for over 600 years. Cafe tables line the curved perimeter where visitors and locals gather to people-watch, savor gelato, and absorb the medieval architecture.

   1 h

2. Siena's magnificent Gothic town hall has anchored the Piazza del Campo since 1310, its elegant facade of brick and travertine marble crowned by the soaring Torre del Mangia. Inside, the Museo Civico houses Ambrogio Lorenzetti's revolutionary Allegory of Good and Bad Government, the first secular frescoes of the Renaissance, alongside Simone Martini's stunning Maestà. The ornate Sala del Mappamondo, Sala della Pace, and Chapel preserve the artistic and political ambitions of medieval Siena.

   Passes by

3. Rising 102 meters above Piazza del Campo, this elegant bell tower was deliberately built to match the height of Siena's cathedral, symbolizing the equal power of church and state in the medieval republic. The tower takes its name from its first bell-ringer, Giovanni di Balduccio, nicknamed Mangiaguadagni (profit-eater) for his spendthrift ways. Climbing the 400 steps rewards visitors with breathtaking views across terracotta rooftops to the Tuscan hills.

   Passes by

4. Siena's cathedral ranks among Italy's most spectacular churches, its black and white striped marble facade and interior creating a dazzling geometric pattern that influenced Tuscan architecture for centuries. The Piccolomini Library preserves Pinturicchio's luminous frescoes depicting the life of Pope Pius II, while Nicola Pisano's carved pulpit and works by Michelangelo and Bernini fill every corner with masterpieces. The unfinished nave extension reveals the cathedral's abandoned ambition before the Black Death devastated the city.

   Passes by

5. Located beneath the cathedral choir, this Gothic baptistery houses a magnificent marble font decorated with bronze panels by the greatest sculptors of the early Renaissance including Ghiberti, Donatello, and Jacopo della Quercia. The hexagonal font's gilded bronze reliefs depicting the life of John the Baptist represent a pivotal moment in art history when Florence and Siena's finest artists collaborated on a single masterpiece. The baptistery's frescoed vaults create an atmosphere of sacred beauty.

   30 min

6. Siena's most elegant street curves from the Campo toward the Duomo, lined with Gothic palaces, artisan workshops, and boutiques selling Sienese specialties from panforte to hand-painted ceramics. The Palazzo Chigi-Saracini houses the prestigious Accademia Musicale Chigiana, its courtyard concerts continuing a tradition of Sienese musical excellence. Window shopping along this atmospheric thoroughfare reveals traditional craft workshops where artisans practice techniques passed down through generations.

   30 min

7. This massive brick Gothic church dominates Siena's skyline from the hill of Camporegio, its austere interior serving as the spiritual home of St. Catherine of Siena, the city's beloved mystic and Doctor of the Church. The Chapel of St. Catherine preserves the saint's head in a gilded reliquary alongside frescoes by Sodoma depicting her ecstasies and miracles. The church's elevated position offers stunning views across the valley to the Duomo.

   30 min

8. The childhood home of St. Catherine has been transformed into a complex of chapels and oratories preserving the rooms where the future saint experienced her mystical visions. Catherine's influence on the medieval church, including persuading Pope Gregory XI to return from Avignon to Rome, made this humble dyer's house a pilgrimage destination decorated with Renaissance frescoes. The intimate spaces convey the domestic origins of one of Christianity's most remarkable women.

   30 min

9. Housed in the Gothic Palazzo Buonsignori, Siena's picture gallery presents the definitive collection of Sienese painting from the 12th to 17th centuries, tracing a distinct artistic tradition that rivaled Florence. Duccio di Buoninsegna, Simone Martini, and the Lorenzetti brothers represent the golden age of Sienese Gothic art, their shimmering gold backgrounds and elegant figures establishing a style that influenced European painting for generations. The chronological arrangement reveals how Sienese artists balanced tradition with innovation.

   Passes by

10. Siena's seventeen contrade each possess a parish church, museum, and distinctive fountain where horses are blessed before the Palio and babies are baptized into their contrada's identity. Walking between these neighborhood fountains reveals the fierce local pride that has divided Siena into competing territories since medieval times, each with its own animal symbol and centuries of victories and defeats. The fountains provide destinations for exploring Siena's residential quarters where flags hang from windows.

    1 h

11. This massive brick fortress was built by Cosimo I de' Medici after Florence's conquest of Siena in 1555, its star-shaped bastions designed to prevent any future rebellion by the subjugated city. Today the fortress has been transformed into a peaceful public park, its grassy ramparts offering sweeping views across Siena and the surrounding countryside. The Enoteca Italiana wine bar occupies the fortress vaults, offering tastings from across Italy in atmospheric brick cellars.

    30 min

12. Perched on a hillside outside Siena's walls, this Renaissance church and monastery was founded by San Bernardino, whose fiery preaching once convinced Sienese women to burn their cosmetics in the Campo. The church's peaceful cloister, terracotta decorations by the Della Robbia workshop, and the saint's simple cell provide a contemplative escape from the busy historic center. The walk through olive groves offers beautiful views of Siena's skyline.

    30 min

Cancellation

Free cancellation up to 24 hours before the experience starts, for a full refund.

Know before you go

How it compares in Siena

• Its from-price is 99% below the median of the 352 experiences we list in Siena.
• It is longer than most of them.
• The operator lists free cancellation on it.

About Siena

Siena is a medieval Tuscan hill city of red-brown brick, known for its shell-shaped main square, its striped cathedral and the twice-yearly Palio.

Siena was Florence's great rival in the Middle Ages, and its historic centre, a UNESCO site, still looks much as it did then. Il Campo, the shell-shaped square, slopes down to the Palazzo Pubblico and its slender tower, the Torre del Mangia. The cathedral, striped in white and dark green marble, has a pavement of inlaid scenes and a library of painted manuscripts.

Top-ranked sights in Siena: Piazza del Campo, Siena Cathedral (Duomo di Siena), Mangia Tower (Torre del Mangia).

See all 352 experiences in Siena