A medieval re-enactment held every September within the walls of the Rocca di Montestaffoli
Medioevo in Rocca is the historical medieval re-enactment that brings the Rocca di Montestaffoli to life every September in the heart of San Gimignano, in the province of Siena. Organized by the Associazione I Cavalieri di Santa Fina, the event transforms the ancient fortress into a bustling medieval village, where costumed figures, musicians, dancers, and soldiers recreate the life and atmosphere of the 14th-century city of towers.
The Cassero of the Rocca di Montestaffoli is the perfect setting for this re-enactment: perched high on the hill, it overlooks San Gimignano and its famous UNESCO-listed towers, offering a unique backdrop of ancient walls, green lawns, and sweeping views of the Tuscan countryside. During the festival, the Rocca fills with encampments, taverns, and corners dedicated to ancient crafts and daily medieval life.
The heart of the event lies in the performances of the drum, clarion, and flag-waving groups, which accompany costumed processions through the historic center up to the Rocca. Visitors can also enjoy medieval dancers, archery demonstrations by the Arcieri di Castelvecchio, and scenes of period life that animate the fortress grounds. It is a program designed for all ages, blending entertainment, history, and popular tradition.
The four Contrade of San GimignanoโSan Matteo, San Giovanni, Castello, and Piazzaโactively participate in the festival by setting up their own taverns inside the walls of the Rocca. Here, guests can enjoy wine and grilled meat along with traditional Tuscan flavors in a convivial atmosphere that lasts well into the evening. The friendly rivalry between the Contrade is one of the most cherished aspects of the local community.
Medioevo in Rocca is the quintessential late-summer medieval event in San Gimignano, complementing the Ferie delle Messi organized by the Cavalieri di Santa Fina in June. The event is part of the Accade d'Estate program, a widespread cultural festival promoted by the Municipality of San Gimignano that offers over eighty events from June to September, including cinema, opera, jazz, re-enactments, and performances throughout the historic center and surrounding areas. For history and tradition enthusiasts, it is the perfect opportunity to discover San Gimignano in a different light, far from the summer tourist crowds.
From September 3 to 6, 2026, the Rocca di Montestaffoli in San Gimignano hosts Medioevo in Rocca, the historical re-enactment organized by the Associazione I Cavalieri di Santa Fina. Four days of shows, costumed processions, performances by drum, clarion, and flag-waving groups, medieval dances, archery demonstrations, and Contrade taverns where you can enjoy wine and grilled meat within the fortress walls.
The event is part of the Accade d'Estate 2026 program, the cultural festival promoted by the Municipality of San Gimignano which brings together over eighty events from June to September. The detailed day-by-day program, including times, processions, and performances, will be published by the Associazione I Cavalieri di Santa Fina in the weeks leading up to the event.
The detailed program for the 2026 edition, including daily times, processions, and performances, will be announced by the Associazione I Cavalieri di Santa Fina in the weeks preceding the event (typically published between late July and August).
Based on previous editions, the event offers over the four days:
Cassero della Rocca di Montestaffoli, San Gimignano (SI), Tuscany. The Rocca can be reached on foot from the historic center in just a few minutes from Piazza del Duomo and Piazza della Cisterna.
By car: take the Poggibonsi Nord exit (from Florence or Siena) on the Florence-Siena highway, then follow signs for San Gimignano; paid parking is available just outside the walls. By train: reach the Poggibonsi-San Gimignano station, then take a bus to San Gimignano (the historic center is closed to traffic).
Free admission. The Rocca is usually open daily during the festival from late morning until evening; the detailed schedule and program are published by the Associazione I Cavalieri di Santa Fina in the weeks leading up to the event.
Wear comfortable shoes for the cobblestone streets of the village and the walk up to the Rocca. The Contrade taverns offer the chance to dine inside the fortress.
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Cassero della Rocca di Montestaffoli
Rocca di Montestaffoli, 53037 San Gimignano