Tuscany — vin santo production is documented from the 14th century in Tuscan monastery records (the name 'holy wine' suggests religious use). Cantucci di Prato are documented from the 16th century. The ritual pairing of the two is a 19th-20th century formalisation of what was already a longstanding Tuscan practice.
Vin Santo is the sacred wine of Tuscany — a passito wine made from trebbiano and malvasia grapes that are dried on racks or hung in well-ventilated rooms until November (the San Martino period), then pressed and fermented in small caratelli (small barrels of chestnut, cherry, or oak) sealed for 3-6 years in the vinsantaia, the attic space where temperature fluctuation catalyses the wine's development. The wine ranges from dry to sweet; the Montepulciano and Chianti versions have the most reputation. The ritual of vin santo con cantucci (dunking the hard, twice-baked almond biscuits into the sweet wine) is the definitive Tuscan end-of-meal tradition — the biscuit absorbs the wine and softens, releasing almond, orange zest, and wine simultaneously.
Vin santo poured into a small glass is amber and slightly viscous; the fragrance is of dried apricot, walnut, and caramel. The cantucci dunked and withdrawn releases almond, orange, and the sweetness of wine. Eaten in two bites, the once-hard biscuit is now soft and wine-soaked, the almond crunching inside the softened crumb. The wine lingers on the palate with caramel and fig. It is the Tuscan aftermeal at its most civilised.
Cantucci (or biscotti di Prato in the Prato tradition) are made from a dry dough of flour, sugar, eggs, whole almonds, and sometimes orange zest and anise seeds, baked once as a log, cooled, then sliced on the diagonal and returned to the oven at lower heat to dry completely. The result is an extremely hard, dry biscuit that can only be eaten comfortably by dunking. The vin santo: pour into small glasses (100ml maximum); dunk cantucci for 3-5 seconds; the biscuit absorbs the wine and is eaten in two bites, still warm from the wine.
The finest Vin Santo (Avignonesi, Isole e Olena, Felsina are benchmark producers) is aged 6-10 years and has a complexity comparable to sherry or Sauternes. The ritual pairing of vin santo e cantucci is the Tuscan dessert — it is not eaten during the meal but after, as a social ritual while conversation continues. Prato claims the original biscotti di Prato recipe (which uses no butter, unlike many imitations).
Over-dunking the cantucci — 3-5 seconds is sufficient; longer and the biscuit disintegrates in the glass. Serving vin santo at the wrong temperature — vin santo should be served at cellar temperature (13-14°C) — not at room temperature (too flat) and not chilled (too closed). Using cheap vin santo — the quality of the wine is the experience; industrially produced vin santo lacks the complexity of farmhouse production.
Slow Food Editore, Toscana in Cucina; Carol Field, The Italian Baker