San Gimignano grew rich on saffron and pilgrims crossing the Via Francigena, then tore itself apart in Guelph-Ghibelline feuds until Florence swallowed it in 1353. Three days of archives in stone: fresco cycles, city gates, hospital pharmacies and a ruined fortress.
Etruscan cinerary urns and Roman glass from the Elsa valley sit beside the reconstructed 16th-century pharmacy of the Spedale di Santa Fina: majolica jars, brass stills and herb ledgers from the hospital that dosed Francigena pilgrims.
This squat arch is the surviving gate of the 10th-century first ring of walls, named for the Becci family who held the towers beside it. Behind it Via del Castello runs through the oldest quarter, past twin Ardinghelli tower stumps.
Benozzo Gozzoli covered the choir in 1464-65 with seventeen scenes from the life of St Augustine, painted while plague ravaged the town. The Romanesque-Gothic hall church of 1280 also holds Piero del Pollaiolo's altarpiece of San Sebastiano.
Ten arches, the oldest Romanesque round ones from 1237 and the pointed Gothic bays added by 1346, shelter the public washing basins fed by a spring below the walls. Wool from the town's cloth trade was rinsed in these troughs.
Dante addressed the council here on 8 May 1300 as Florence's Guelph envoy, under Lippo Memmi's 1317 Maestà. Upstairs, Memmo di Filippuccio's private chamber cycle shows a couple bathing and bedding — rare secular painting of about 1310.
Florence built this pentagonal fortress in 1353, the year after San Gimignano surrendered its independence, then Cosimo I had it slighted in 1558. Only one tower and the curtain walls survive, ringed by olives on the town's highest point.
Housed beside the Collegiata's cloister, it gathers what was stripped from parish churches: Benedetto da Maiano's marble bust of Sant'Antonio, illuminated choir books, and Bartolo di Fredi's panels rescued after the 1944 bomb damage.
The pointed Sienese-style gate of 1262 marks where the walls were pushed out to enclose the Borgo San Matteo. Its outer arch still shows the grooves of the portcullis and the corbels of the vanished defensive gallery above.
The FAI opened this merchant house-tower in 2015 exactly as the Campatelli family left it in 2005: 19th-century furnishings, family photographs, and a 28 m tower shaft you can look up from the ground floor with a projected town history.
The Via Francigena's course through town, lined with pilgrim hospices and the Pisan-striped facade of San Francesco. The 1262 gate at the bottom keeps its Arab-influenced pointed arch, built when Siena controlled the road south.
Thirteen kilometres north, the brick hill town keeps the house where Boccaccio died in 1375, rebuilt after 1944 shelling, with his study, a Decameron library and a tower view. Palazzo Pretorio nearby holds Renaissance podestà coats of arms.
A stark 12th-century Romanesque country parish church of travertine, 4 km west, with no facade decoration and a single apse. Gabriele d'Annunzio set his 1902 tragedy La figlia di Iorio in its setting after visiting in 1899.