San Gimignano is a walled hilltop town in the province of Siena in Tuscany, central Italy — a municipality of 7,700 people (only about 1,000 live within the medieval walls) whose medieval skyline of 14 surviving towers (out of 72 towers built during the height of the town's power, 13th-14th century — the tower-building mania of medieval Italian city-states: wealthy families built ever-taller towers to display their power and provide refuge in the frequent civil conflicts between rival factions) makes it one of the most immediately recognisable townscapes in the world. San Gimignano (UNESCO World Heritage since 1990, cited for its extraordinary state of medieval preservation and the tower skyline) sits at 334 m altitude in the Val d'Elsa valley, 57 km south of Florence, 38 km northwest of Siena, surrounded by vineyards producing Vernaccia di San Gimignano (the first Italian wine to receive DOC status in 1966 and DOCG status in 1993 — the unique white wine grape variety that grows only in the San Gimignano area, making wines of delicate floral and almond character that pair with the local wild boar, saffron and truffle cuisine). Medieval San Gimignano was wealthy from its position on the Via Francigena (the medieval pilgrimage and trade road from Canterbury to Rome, passing through San Gimignano), and from its monopoly on the trade of saffron (zafferano, from the Crocus sativus grown in the surrounding Val d'Elsa fields — the most expensive spice in the world by weight, used medicinally and as a dye in medieval Europe; San Gimignano saffron DOP is the world's finest). The Piazza della Cisterna (the main triangular medieval square, paved with herringbone brick, with its 1237 well) and the Piazza del Duomo (the adjacent square with the Collegiata and the towers) form the finest medieval civic space in Tuscany.
The Torre Grossa (the Big Tower, 54 m — the tallest of San Gimignano's surviving 14 towers, built by the comune/municipality rather than a private family; the only tower the public can climb) gives the definitive San Gimignano view: looking down and across at the other 13 towers rising from the medieval townscape at different heights, the Tuscan hills stretching to the horizon on all sides, the Collegiata facade in the Piazza del Duomo below, and — on clear days — the towers of Volterra 30 km southwest. The tower museum entry includes the Palazzo del Popolo and the Museo Civico (the civic museum with Lippo Memmi's Maestà and Taddeo di Bartolo's cycle of scenes from the life of San Gimignano).
🎫 Book tickets via GetYourGuideThe Collegiata (the 11th-century Romanesque collegiate church, the dominant building of San Gimignano, with a remarkably plain facade that contrasts with one of the most completely frescoed interiors in Italy) has three complete fresco cycles covering the Old Testament left nave (Bartolo di Fredi, c.1367 — 26 scenes from Genesis, Noah and Job including a rare pre-Renaissance Flood scene with floating drowned bodies), the New Testament right nave (Barna da Siena, c.1340-1350), the Last Judgement west wall (Taddeo di Bartolo, 1393 — the most explicitly graphic Hell scene in Tuscany), and the Cappella di Santa Fina (Ghirlandaio, 1475-1477 — the finest Renaissance chapel in San Gimignano, commissioned by the family of the local saint).
🎫 Book tickets via GetYourGuideThe Vernaccia di San Gimignano (DOCG, the indigenous white wine grape of San Gimignano — mentioned in records since 1276; Dante Alighieri mentioned it in the Purgatorio; the first wine in Italy to receive DOC status in 1966; the grape produces wines of delicate floral and almond aromas with crisp minerality from the Pliocene marine fossil-rich soils of the Val d'Elsa) is the essential San Gimignano wine experience; tasting at the Vernaccia di San Gimignano Wine Experience (DOCG museum + tasting, Rocca di Montestaffoli) or at the Tenuta Abbazia Monte Oliveto, Mormoraia or Cappella Sant'Andrea wineries in the surrounding hills.
🎫 Book tickets via GetYourGuideThe Piazza della Cisterna (the lower of San Gimignano's two main squares, triangular, paved in herringbone brick, centred on the 1237 travertine well — the cisterna that gave the square its name; surrounded by the 13th-14th century tower-houses and merchant palaces of the rival Ardinghelli and Salvucci families who built competing towers; the towers of the Ardinghelli family on the southwest and the Salvucci twin towers on the north anchor the square) at golden hour (when the warm Tuscan light rakes across the brick paving and the travertine well glows) is the finest medieval townscape in Italy at its most photogenic.
The San Gimignano cuisine: pappardelle al cinghiale (wide pasta ribbons in wild boar ragù — the Tuscan forest wild boar, hunted in the Chianti hills, slow-braised with juniper, rosemary and red wine into a rich dark sauce); risotto allo zafferano (risotto with San Gimignano DOP saffron — the local golden-yellow saffron that produces the world's finest risotto Milanese equivalent); the San Gimignano gelato at Sergio Dondoli's Gelateria di Piazza (the gelatiere who won the World Gelato Championship 4 times and whose Vernaccia sorbet is the most unusual gelato in Tuscany).
San Vivaldo (18 km northwest of San Gimignano, the remote hilltop Franciscan sanctuary founded where the hermit Vivaldo di Lazzaro died in 1320) has a Sacred Mountain (sacro monte) of 34 miniature chapels (1500-1515) recreating the holy places of Jerusalem at 1:1 scale — the Via Crucis, the Garden of Gethsemane, the Cenacle, the Praetorium, Calvary and the Holy Sepulchre — designed for pilgrims who could not afford the Jerusalem journey; the terracotta figures inside (hundreds of polychrome terracotta figures by Giovanni della Robbia's workshop and Benedetto Buglioni) are a remarkable survival of early 16th-century devotional art.
🎫 Book tickets via GetYourGuideVolterra (30 km southwest of San Gimignano, the Etruscan city of Velathri — one of the 12 cities of the Etruscan League — now a medieval hilltop city of 11,000 known for the Twilight film series setting (the Volturi vampire clan headquarters), the alabaster crafting tradition (the Volterra alabaster quarries have been worked since Etruscan times; the local artisans produce the finest alabaster sculpture in Italy), the Etruscan Museum (the Guarnacci with the finest collection of Etruscan funerary urns in the world — 600 alabaster cinerary urns), and the Roman Theatre (1st century BC, the best-preserved Roman theatre in Tuscany).
🎫 Book tickets via GetYourGuideThe Val d'Elsa countryside around San Gimignano (the classic "Tuscan landscape" with its cypress-lined roads, the rolling golden hills, the isolated farmhouses, the vineyards and olive groves) is the landscape that appears in the backgrounds of every Ghirlandaio, Botticelli and Leonardo painting — specifically the hill of San Gimignano appears in Ghirlandaio's frescoes in Florence's Santa Trinita and Ognissanti; the saffron Crocus sativus fields (planted in rows of pale purple flowering plants in October-November) are the crop that made San Gimignano wealthy in the medieval period and is now being revived as a DOP product.
The Rocca di Montestaffoli (the 14th-century Florentine fortress at the western end of San Gimignano, now partly converted to the Vernaccia wine experience museum) has the best sunset view in the town — the golden light over the Val d'Elsa, the cypress-lined roads, the vineyards below the walls and the first stars appearing over the Apennines to the east; the Cantina della Rocca serves Vernaccia and local bruschetta with lard, honey and rosemary on the fortress walls as the sun sets over the Tyrrhenian coast (visible on clear days from the tower).
Siena (38 km southeast of San Gimignano by car or bus) has the Piazza del Campo — the scallop-shell shaped medieval civic square on which the Palio di Siena horse race (2 July and 16 August: 10 of the 17 city contrade/districts race bareback horses around the Campo in 90 seconds, the most intense and dangerous horse race in Europe; the contrade prepare for the race all year; the Palio determines the social hierarchy of Siena for the following 12 months) is run; the square's pavement slopes at 8 degrees to give every spectator a clear view; the Torre del Mangia (87 m, the second-tallest medieval tower in Italy, with 505 steps to the top for the finest view of Siena) and the Palazzo Pubblico.
🎫 Book tickets via GetYourGuideThe Siena Duomo (the Cathedral of Santa Maria Assunta, 1220-1380 — the most ambitious Gothic cathedral in Italy after the French cathedrals; the alternating black and white marble striped facade and striped campanile; the extraordinary marble inlaid floor of the nave — 56 panels of intarsia marble depicting sibyls, allegories and historical scenes made between 1372 and 1547, the finest decorative floor in any cathedral in the world; the Piccolomini Library within — frescoed by Pinturicchio with the life of Pope Pius II in a room of perfect Renaissance decorative harmony) and the Museo dell'Opera with Duccio's Maestà.
🎫 Book tickets via GetYourGuideReturn to San Gimignano for the evening — if visiting in October-November, the saffron harvest (the hand-picking of the Crocus sativus flowers at dawn, the separation of the three stigmas from each flower, the drying — 150,000 flowers are needed to produce 1 kg of dried saffron; the DOP San Gimignano saffron is the most expensive per gram of any food ingredient in Tuscany except white truffle) can be visited at participating farms; the farewell dinner at Bel Soggiorno or Dulcisinfundo — the signature San Gimignano pasta with local saffron, wild boar ragu and Vernaccia wine.
San Gimignano empties of day-trippers after 6pm (the vast majority of visitors are day trips from Florence or Siena — typically 10am-5pm) and the evening town is a completely different experience: the Piazza della Cisterna with its medieval wells and towers lit by the street lanterns, the Colleggiata square quiet, the few restaurants serving late Tuscan dinners, the towers visible against the dark Tuscan sky — this is the medieval San Gimignano that the tower-building families of the 13th century inhabited; the only sounds are the bells of the Collegiata and the occasional moped.